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Martha's Vineyard Vacation Rentals

Oak Bluffs Vacation Rentals

Oak Bluffs is known for its whimsical "gingerbread" houses, many of which were built in the nineteenth century. A popular family vacation area, Oak Bluffs has several public parks, including Ocean Park with its live music throughout the summer.

231 Vacation Properties in Oak Bluffs
Sleeps

Oak Bluffs vacation rentals that sleep 20

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Oak Bluffs
ID 5533
9 BR
4 baths
Sleeps 20
Villa Rosa- Historic Waterfront Victorian Mansion 1875 Gem
Villa Rosa- Historic Waterfront Victorian Mansion 1875 Gem
Distance to beach: Across the street (no obstruction) Oak Bluffs Town Beach and 5 min drive, 15 min bike State Beach
6 reviews read reviews
Summer:
 $20,000 - $75,000/wk
Off Season:
 $2,200 - $3,000/night
 $10,000 - $25,000/wk
 $30,000 - $60,000/mo

Oak Bluffs vacation rentals that sleep 18

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Oak Bluffs
ID 38152
9 BR
6 ½ baths
Sleeps 18
Spectacular Views Completely Updated w/Guest Home- Sleeps 18
Spectacular Views Completely Updated w/Guest Home- Sleeps 18
Distance to beach: 2/10 mi to Oak Bluffs Town Beach
Summer:
 $26,000 - $32,000/wk
Off Season:
 $1,200 - $1,500/night
 $10,000 - $30,000/wk
Oak Bluffs
ID 39396
9 BR
3 ½ baths
Sleeps 18
OCEANFRONT, 9BR,AC,WALK TO FERRY AND TOWN
OCEANFRONT, 9BR,AC,WALK TO FERRY AND TOWN
Distance to beach: Inkwell Beach, State Beach, East ville Beach
OWNER SPECIAL:
"Escape the Ordinary- Experience the Unforgettable" 9 BR, All Summer 2025 OPEN, BOOK NOW.
Summer:
 $18,000 - $32,000/wk
Off Season:
 $17,000 - $18,000/wk

Oak Bluffs vacation rentals that sleep 16

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Historic Copeland District
ID 35193
8 BR
3 baths
Sleeps 16
8 BR Grand Victorian near Inkwell Beach sleeps 16 people!
8 BR Grand Victorian near Inkwell Beach sleeps 16 people!
Distance to beach: 2/10 mi to Oak Bluffs Town Beach
Summer:
 $13,700 - $19,500/wk
Off Season:
 $1,500 - $2,000/night
 $9,500 - $11,700/wk
East Chop-Oak Bluffs
ID 14646
8 BR
3 baths
Sleeps 16
Historic East Chop Beach House - with AC units
Historic East Chop Beach House - with AC units
Distance to beach: 300 ft to Jetty Beach
7 reviews read reviews
Summer:
 $10,500 - $14,000/wk
Off Season:
 $9,000 - $10,500/wk
3
Oak Bluffs
ID 28357
6 BR
4 ½ baths
Sleeps 16
Beautiful, Newly Updated, Spacious 6 BR Home
Beautiful, Newly Updated, Spacious 6 BR Home
Distance to beach: 3 miles to Oak Bluffs Inkwell Beach
15 reviews read reviews
Summer:
 $12,000 - $15,000/wk
Off Season:
 $10,000 - $12,000/wk
5
Oak Bluffs
ID 19801
6 BR
4 ½ baths
Sleeps 16
Modern Renovated 6 bedroom Beautiful Pool, hot tub and pond
Modern Renovated 6 bedroom Beautiful Pool, hot tub and pond
Distance to beach: 1.5 miles State Beach and 15 Minutes to State Beach
4 reviews read reviews
Off Season:
 $1,500 - $2,000/night
 $12,000 - $16,500/wk
4

Oak Bluffs vacation rentals that sleep 15

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Oak Bluffs
ID 11056
6 BR
2 ½ baths
Sleeps 15
Beach, Town, and Tennis, Central AC, 100% Renew. Energy.
Beach, Town, and Tennis, Central AC, 100% Renew. Energy.
Distance to beach: 3/10 mi to Inkwell Beach, Oak Bluffs
13 reviews read reviews
Summer:
 $7,900 - $9,800/wk
Off Season:
 $3,500 - $7,900/wk
4
Oak Bluffs
ID 39526
6 BR
4 baths
Sleeps 15
Island Escape with Water-Views; Lap Pool & Guest House
Island Escape with Water-Views; Lap Pool & Guest House
Distance to beach: 1 mi to The Jetty Beach and 1/2 mi to Eastville Beach
Summer:
 $17,500 - $21,000/wk
 $50,000 - $80,000/mo
Off Season:
 $1,500/night
 $10,500 - $13,000/wk
 $6,000 - $50,000/mo
5

Oak Bluffs vacation rentals that sleep 14

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Oak Bluffs
ID 35126
7 BR
4 baths
Sleeps 14
Historic Victorian Home With Ocean Views & AC
Historic Victorian Home With Ocean Views & AC
Distance to beach: 0.3 mile Oak Bluffs Town Beach
Summer:
 $14,500 - $21,700/wk
Off Season:
 $7,000 - $16,500/wk
Oak Bluffs
ID 26970
5 BR
2 ½ baths
Sleeps 14
AMENITIES GALORE, DOCK/TENNIS/AC IN PRIVATE COMMUNITY
AMENITIES GALORE, DOCK/TENNIS/AC IN PRIVATE COMMUNITY
Distance to beach: 3 miles to Joseph Sylvia State Beach
3 reviews read reviews
Summer:
 $7,500 - $12,000/wk
Off Season:
 $5,000 - $7,500/wk
2
Oak Bluffs
ID 39105
5 BR
4 ½ baths
Sleeps 14
The Driftwood House Waterfront Retreat, Walk to the Inkwell
The Driftwood House Waterfront Retreat, Walk to the Inkwell
Distance to beach: 3/10 mi to Oak Bluffs Town Beach
3 reviews read reviews
Summer:
 $15,000 - $22,000/wk
Off Season:
 $7,000 - $22,000/wk
4

Oak Bluffs vacation rentals that sleep 13

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Oak Bluffs
ID 35046
6 BR
2 baths
Sleeps 13
Air Conditioned Oak Bluffs Waterview Victorian. In Town
Air Conditioned Oak Bluffs Waterview Victorian. In Town
Distance to beach: 2/10 mi to Oak Bluffs Town Beach
10 reviews read reviews
Summer:
 $6,750 - $12,000/wk
Off Season:
 $3,000 - $6,750/wk

Oak Bluffs vacation rentals that sleep 12

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Oak Bluffs
ID 32999
7 BR
2 ½ baths
Sleeps 12
In Town Oak Bluffs w/AC Beautifully Renovated Victorian
In Town Oak Bluffs w/AC Beautifully Renovated Victorian
Distance to beach: 3/10 mile To Oak Bluffs Town Beach
11 reviews read reviews
Summer:
 $9,000 - $12,000/wk
Off Season:
 $9,000/wk
6
Oak Bluffs (East Chop)
ID 11709
6 BR
4 baths
Sleeps 12
Martha's Vineyard Memories, 1860 Sea Captain's Beach Home!
Martha's Vineyard Memories, 1860 Sea Captain's Beach Home!
Distance to beach: 5 minute bike ride to Sunny Jetty Beach!
12 reviews read reviews
Summer:
 $7,999/wk
Off Season:
 $7,999/wk
2
East Chop
ID 23099
6 BR
4 ½ baths
Sleeps 12
Family Compound on East Chop
Family Compound on East Chop
Distance to beach: two tenths mile to lovely Jetty Beach
2 reviews read reviews
Summer:
 $5,700 - $8,500/wk
Off Season:
 $800/night
 $3,000 - $6,500/wk
East Chop
ID 23424
6 BR
4 ½ baths
Sleeps 12
Large Cottage! Walk to Town and Beach! BOOKING 2025!
Large Cottage! Walk to Town and Beach! BOOKING 2025!
Distance to beach: 3/10 of a mile, 5 minute walk The Jetty Beach
3 reviews read reviews
Off Season:
 $800 - $1,500/night
 $2,000 - $4,000/wk
4
Oak Bluffs
ID 33717
6 BR
3 baths
Sleeps 12
''The Carousel House'' - Ocean Park - Featured in NY Times
''The Carousel House'' - Ocean Park - Featured in NY Times
Distance to beach: 0.2 mi to Oak Bluffs Town Beach
1 review read review
Summer:
 $12,900 - $20,900/wk
Off Season:
 $1,575/night
 $11,025 - $12,900/wk
2
Oak Bluffs
ID 34066
6 BR
3 baths
Sleeps 12
Beautiful Victorian 6 BR home in the heart of Oak Bluffs
Beautiful Victorian 6 BR home in the heart of Oak Bluffs
Distance to beach: 0.2 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
Booking now for 2025!
Summer:
 $14,900 - $20,900/wk
Off Season:
 $9,900 - $12,900/wk
Oak Bluffs
ID 38331
6 BR
3 ½ baths
Sleeps 12
6 Bedroom house for rent in Oak Bluffs, sleeps 12
6 Bedroom house for rent in Oak Bluffs, sleeps 12
Distance to beach: 0.2 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
We are ready to book for 2025!
Summer:
 $8,500 - $11,500/wk
Off Season:
 $8,500 - $11,500/wk
Highlands Section of East Chop
ID 8766
6 BR
2 baths
Sleeps 12
Oak Bluffs Harbor view...walk to town & beach
Oak Bluffs Harbor view...walk to town & beach
Distance to beach: 6/10 mile to Oak Bluffs Town Beach and 3/10 mile to public Jetty Beach
31 reviews read reviews
Summer:
 $6,000 - $6,500/wk
Off Season:
 $850 - $1,050/night
 $6,000/wk
Oak Bluffs
ID 22593
6 BR
3 baths
Sleeps 12
Charming 5+ BR Renovated Camp on Lagoon Pond w/ Guest Cabin
Charming 5+ BR Renovated Camp on Lagoon Pond w/ Guest Cabin
Distance to beach: Private beach on the Lagoon
9 reviews read reviews
Off Season:
 $600 - $900/night
 $6,000 - $7,000/wk
6
East Chop
ID 20680
6 BR
2 baths
Sleeps 12
East Chop Martha’s Vineyard Waterfront Ocean View Rental
East Chop Martha’s Vineyard Waterfront Ocean View Rental
Distance to beach: 2/10 mile to Jetty Beach
2 reviews read reviews
Summer:
 $6,000 - $8,000/wk
Off Season:
 $5,000 - $7,000/wk
The Radcliffe House
ID 37237
6 BR
2 baths
Sleeps 12
Beautiful newly renovated 6bd/ 3 block from beach
Beautiful newly renovated 6bd/ 3 block from beach
Distance to beach: 4/10 mi to Oak Bluffs Town Beach
7 reviews read reviews
Summer:
 $7,500 - $10,500/wk
Off Season:
 $645 - $2,000/night
 $5,000 - $8,000/wk
Oak Bluffs
ID 37925
6 BR
4 baths
Sleeps 12
Oak Bluffs Luxury Compound with Carriage House & Pool/Spa
Oak Bluffs Luxury Compound with Carriage House & Pool/Spa
Distance to beach: 3.7 miles to Inkwell Beach Oak Bluffs Town Beach and 8.7 miles to South Beach (Katama) South Beach - Katama
5
Oak Bluffs
ID 11575
5 BR
3 ½ baths
Sleeps 12
Joy, historic 5 bedroom home in the heart Oak Bluffs
Joy, historic 5 bedroom home in the heart Oak Bluffs
Distance to beach: 1/2 mile
1 review read review
Summer:
 $3,500 - $4,200/wk
Off Season:
 $2,000 - $2,800/night
 $3,000 - $3,500/wk
3
Harthaven
ID 31261
5 BR
3 ½ baths
Sleeps 12
The Beach House: Historic Harthaven Gem on a Private Beach
The Beach House: Historic Harthaven Gem on a Private Beach
Distance to beach: On a private beach & next to an association beach
1 review read review
Summer:
 $8,500 - $9,500/wk
Off Season:
 $6,500 - $9,000/wk
Oak Bluffs
ID 32994
5 BR
3 baths
Sleeps 12
Walk to Town & Beach from this Beautiful Waban Park Cottage
Walk to Town & Beach from this Beautiful Waban Park Cottage
Distance to beach: 2 blocks to Oak Bluffs Town Beach
11 reviews read reviews
Summer:
 $6,000 - $10,000/wk
Off Season:
 $4,500 - $5,500/wk
Oak Bluffs
ID 38997
5 BR
2 baths
Sleeps 12
** Newly Renovated home 2 Minutes away from Circuit Ave
** Newly Renovated home 2 Minutes away from Circuit Ave
Distance to beach: 1.4 mi to Oak Bluffs Town Beach
2 reviews read reviews
Summer:
 $5,500 - $8,500/wk
 $26,300 - $30,000/mo
Off Season:
 $500 - $860/night
 $3,300 - $7,000/wk
 $2,800 - $28,000/mo
4
Oak Bluffs
ID 39247
5 BR
6 ½ baths
Sleeps 12
Grand Coastal-Style Estate In The Preserve With Pool/Hot Tub
Grand Coastal-Style Estate In The Preserve With Pool/Hot Tub
Distance to beach: 3.3 mi to Oak Bluffs Town Beach
1 review read review
Summer:
 $20,000 - $30,000/wk
Off Season:
 $1,500 - $3,145/night
 $10,000 - $17,500/wk
Oak Bluffs
ID 31220
5 BR
2 ½ baths
Sleeps 12
CENTRAL AC! Walk 2 Town and Beach. Game room w/arcade games
CENTRAL AC! Walk 2 Town and Beach. Game room w/arcade games
Distance to beach: 1/2 mile to Jetty beach
16 reviews read reviews
Summer:
 $6,000 - $7,300/wk
Off Season:
 $7,300/wk
3
East Chop
ID 37848
5 BR
5 ½ baths
Sleeps 12
Black Ivy Cottage - Direct Oceanfront in East Chop/Sleeps 12
Black Ivy Cottage - Direct Oceanfront in East Chop/Sleeps 12
Distance to beach: 1/10 mi to The Jetty Beach and 1/10 mi to Oak Bluffs Town Beach
1 review read review
Summer:
 $15,000 - $20,000/wk
Off Season:
 $1,500 - $1,660/night
 $10,000 - $15,000/wk
3
Lagoon Pond Salt-Waterfront
ID 27817
4 BR
3 ½ baths
Sleeps 12
Glorious Sunsets On and Over the Water. Beautiful Home
Glorious Sunsets On and Over the Water. Beautiful Home
Distance to beach: Private beach, 4kayaks,4-SUPs, beach chairs & toys
30 reviews read reviews
Summer:
 $14,000 - $20,000/wk
Off Season:
 $2,000 - $2,500/night
 $6,000 - $140,000/wk
 $25,000 - $30,000/mo
11
Oak Bluffs
ID 37162
4 BR
2 ½ baths
Sleeps 12
Vineyard Seven/Sleeps 12/Tennis Courts/Centrally Located
Vineyard Seven/Sleeps 12/Tennis Courts/Centrally Located
Distance to beach: 2.7 mi to Oak Bluffs Town Beach
1 review read review
Summer:
 $6,000 - $16,000/wk
Off Season:
 $850 - $925/night
 $3,000 - $10,500/wk
Oak Bluffs
ID 38518
4 BR
3 baths
Sleeps 12
Pool, Hot Tub, Pool Bar...Perfect for Entertaining!
Pool, Hot Tub, Pool Bar...Perfect for Entertaining!
Distance to beach: 3.6 mi to Oak Bluffs Town Beach
Off Season:
 $1,375 - $1,600/night
 $5,000/wk
2

Oak Bluffs vacation rentals that sleep 11

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East Chop
ID 34693
5 BR
5 ½ baths
Sleeps 11
East Chop Beautiful Renovated Cottage, 5 Bedrooms + 5 Baths
East Chop Beautiful Renovated Cottage, 5 Bedrooms + 5 Baths
Distance to beach: 7/10 mi to The Jetty Beach
2 reviews read reviews
Summer:
 $7,500 - $10,500/wk
Off Season:
 $750 - $950/night
 $5,000 - $6,500/wk
5
Oak Bluffs
ID 35433
5 BR
4 baths
Sleeps 11
Beautiful home, Game Room/pool table, Large Patio & Yard
Beautiful home, Game Room/pool table, Large Patio & Yard
Distance to beach: 2.9 mi to Oak Bluffs Town Beach and 4.0 mi to State Beach
3 reviews read reviews
Summer:
 $6,900 - $8,800/wk
Off Season:
 $750 - $800/night
 $2,000 - $8,600/wk
2
Harthaven/Oak Bluffs
ID 39344
5 BR
4 ½ baths
Sleeps 11
Five Bedroom Property in Harthaven, Oak Bluffs
Five Bedroom Property in Harthaven, Oak Bluffs
Distance to beach: Less than 1/2 mile to Harthaven Association Beach
Summer:
 $13,000 - $15,000/wk
Off Season:
 $13,000/wk
Oak Bluffs
ID 33881
5 BR
1 ½ bath
Sleeps 11
Beach and downtown OB walkable! 5 Bedroom Victorian.
Beach and downtown OB walkable! 5 Bedroom Victorian.
Distance to beach: 3/10 mi to Oak Bluffs Town Beach
3 reviews read reviews
Summer:
 $8,000/wk
Off Season:
 $3,000 - $4,500/wk
East Chop
ID 34601
4 BR
3 baths
Sleeps 11
Dempster Park of East Chop: Walk to Beach & Town!
Dempster Park of East Chop: Walk to Beach & Town!
Distance to beach: Jetty Beach Oak Bluffs Town Beach
7 reviews read reviews
Summer:
 $6,000 - $8,000/wk
Off Season:
 $571/night
 $4,000 - $6,000/wk
5
Oak Bluffs
ID 39520
4 BR
4 baths
Sleeps 11
Heated Pool/Spa/Poolhouse; Home Theatre, Outdoor Dining
Heated Pool/Spa/Poolhouse; Home Theatre, Outdoor Dining
Distance to beach: 2.2 mi to Oak Bluffs Town Beach
Summer:
 $20,000 - $25,000/wk
 $67,000 - $80,000/mo
Off Season:
 $2,000 - $3,000/night
 $15,000 - $25,000/wk
 $45,000 - $61,000/mo
5

Oak Bluffs vacation rentals that sleep 10

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Oak Bluffs
ID 18823
6 BR
2 baths
Sleeps 10
Charming, 6 Bedroom Victorian Gingerbread
Charming, 6 Bedroom Victorian Gingerbread
Distance to beach: One block State Beach and One block to Sea View Ave & Town Beach.
12 reviews read reviews
Summer:
 $7,500 - $8,500/wk
Off Season:
 $7,500/wk
4
Oak Bluffs
ID 29386
6 BR
2 baths
Sleeps 10
Charming House on Waban Park, Walk to Beach, Town, & Ferry!
Charming House on Waban Park, Walk to Beach, Town, & Ferry!
Distance to beach: 2 blocks from the Inkwell (Town Beach)
7 reviews read reviews
Summer:
 $4,500 - $10,000/wk
Off Season:
 $2,000 - $6,900/wk
3
Oak Bluffs
ID 12900
6 BR
3 baths
Sleeps 10
Classic Vineyard Ocean, Harbor, Lake & Parkview Cottage w/AC
Classic Vineyard Ocean, Harbor, Lake & Parkview Cottage w/AC
Distance to beach: 3/10 mi to Jetty Beach
3 reviews read reviews
Summer:
 $6,200 - $7,000/wk
Off Season:
 $2,000/night
 $4,000/wk
2
Oak Bluffs
ID 4132
5 BR
3 baths
Sleeps 10
Waterfront with its own Private Sandy Beach ! ! !
Waterfront with its own Private Sandy Beach ! ! !
Distance to beach: 0 feet to our beach; 1-1/2 miles to Vinyd beaches
6 reviews read reviews
Summer:
 $6,500 - $7,900/wk
Off Season:
 $1,000 - $7,900/wk
2
Oak Bluffs
ID 3540
5 BR
3 baths
Sleeps 10
Magnificent Spacious Modern Home
Magnificent Spacious Modern Home
Distance to beach: O.7 miles Oak Bluffs Town Beach and 0.7 miles Eastville Beach
8 reviews read reviews
Summer:
 $5,000 - $6,500/wk
Off Season:
 $2,000 - $6,500/wk
 $3,500 - $5,000/mo
2
Oak Bluffs
ID 11040
5 BR
2 baths
Sleeps 10
Ocean Peek Cottage
Ocean Peek Cottage
Distance to beach: Two blocks
6 reviews read reviews
Summer:
 $4,200 - $4,600/wk
Off Season:
 $1,500 - $4,600/wk
2
Oak Bluffs
ID 19414
5 BR
2 baths
Sleeps 10
No need for car -- walk from ferry! Beach & water views
No need for car -- walk from ferry! Beach & water views
Distance to beach: ~30 yards to Inkwell Beach
3 reviews read reviews
Summer:
 $7,000 - $12,200/wk
Off Season:
 $7,000 - $10,000/wk
3
Oak Bluffs
ID 27415
5 BR
2 baths
Sleeps 10
Two weeks left for 2025. Don't wait.
Two weeks left for 2025. Don't wait.
Distance to beach: Inkwell beach under a 1/2 mile
25 reviews read reviews
Summer:
 $5,000 - $6,000/wk
Off Season:
 $4,000 - $4,500/wk
3
Oak Bluffs
ID 28697
5 BR
2 ½ baths
Sleeps 10
Great Location. Central AC. Easy walk to town & beach!
Great Location. Central AC. Easy walk to town & beach!
Distance to beach: Town / Inkwell Beach yards away
1 review read review
OWNER SPECIAL:
GREAT WEEKS STILL OPEN, JUNE 7TH,14TH & 21ST ;AUGUST 23RD & 30TH 2025 ARE OPEN!
Summer:
 $9,000 - $16,500/wk
Off Season:
 $8,000 - $9,500/wk
Oak Bluffs
ID 34051
5 BR
2 baths
Sleeps 10
5 BR on Quiet East Chop Street, Steps to Beach
5 BR on Quiet East Chop Street, Steps to Beach
Distance to beach: 0.3 mi to The Jetty Beach
7 reviews read reviews
Summer:
 $4,350 - $6,850/wk
Off Season:
 $575/night
 $4,150 - $4,350/wk
2
Oak Bluffs
ID 34390
5 BR
3 baths
Sleeps 10
This is one Summer School you won't want to miss!
This is one Summer School you won't want to miss!
Distance to beach: 7/10 mi to Oak Bluffs Town Beach
3 reviews read reviews
Summer:
 $7,000 - $11,000/wk
Off Season:
 $5,000 - $7,750/wk
4
Oak Bluffs
ID 34661
5 BR
5 ½ baths
Sleeps 10
5 BR SUITES, SALT WATER POOL, CENTRAL AIR, BIKE PATH
5 BR SUITES, SALT WATER POOL, CENTRAL AIR, BIKE PATH
Distance to beach: 3.3 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
2025 WEEKS ARE STILL AVAILABE FOR JULY BOOK NOW BEFORE THEY GO !
Summer:
 $15,000 - $30,000/wk
Off Season:
 $15,000/wk
Preserves
ID 33665
5 BR
5 ½ baths
Sleeps 10
5 BR SUITES, CENTRAL AIR, TRAILS, BIKE PATH, FARM NECK!
5 BR SUITES, CENTRAL AIR, TRAILS, BIKE PATH, FARM NECK!
Distance to beach: 3.4 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
Do not miss out , August 17th OPEN book now best week of the season!
Summer:
 $14,500 - $18,500/wk
Off Season:
 $12,000 - $14,500/wk
Oak Bluffs
ID 35217
5 BR
3 baths
Sleeps 10
The “Summer Wind” House - Walk to the Beach!
The “Summer Wind” House - Walk to the Beach!
Distance to beach: 3/10 mi to Oak Bluffs Town Beach
2 reviews read reviews
Summer:
 $9,000 - $17,000/wk
Off Season:
 $6,000 - $10,000/wk
Oak Bluffs
ID 34873
5 BR
2 baths
Sleeps 10
5 BR , Walk to Town and Inkwell Beach, Sleeps 10
5 BR , Walk to Town and Inkwell Beach, Sleeps 10
Distance to beach: 2/10 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
2025 WEEKS ARE STILL AVAILABE FOR JULY BOOK NOW BEFORE THEY GO,.
Summer:
 $8,750 - $12,750/wk
Off Season:
 $8,750 - $10,750/wk
Oak Bluffs
ID 34333
5 BR
3 baths
Sleeps 10
The Mission House Waterviews of Nantucket Sound & Farm Pond
The Mission House Waterviews of Nantucket Sound & Farm Pond
Distance to beach: 2/10 mi to Oak Bluffs Town Beach and 1/10 mi to Inkwell Beach
1 review read review
OWNER SPECIAL:
Due to a Cancellation, Two week rental Aug 9-23 available!! Grand Illumination & OB Fireworks.
Summer:
 $13,500 - $16,000/wk
Off Season:
 $8,000/wk
3
Waterview Farm
ID 38347
5 BR
2 ½ baths
Sleeps 10
Family Retreat in Private Setting
Family Retreat in Private Setting
Distance to beach: 1/2mi Oak Bluffs Town Beach and 2 miles - State Beach
Summer:
 $15,000 - $16,000/wk
Off Season:
 $1,250 - $1,500/night
 $15,000/wk
7
Oak Bluffs
ID 38822
5 BR
4 baths
Sleeps 10
Stylish In-town Gingerbread in the Center of EVERYTHING!
Stylish In-town Gingerbread in the Center of EVERYTHING!
Distance to beach: 2/10 mi to Oak Bluffs Town Beach
3 reviews read reviews
Summer:
 $6,000 - $16,000/wk
Off Season:
 $900 - $1,200/night
 $5,000 - $12,000/wk
Oak Bluffs
ID 39273
5 BR
3 ½ baths
Sleeps 10
5 BR Victorian, AC, OCEAN PARK, FERRY,BEACHES,TOWN
5 BR Victorian, AC, OCEAN PARK, FERRY,BEACHES,TOWN
Distance to beach: Across the Street to Town/Inkwell Beaches
OWNER SPECIAL:
Now booking for 2025!
Summer:
 $7,500 - $14,000/wk
Off Season:
 $7,000 - $8,000/wk
Oak Bluffs
ID 26885
5 BR
1 ½ bath
Sleeps 10
Great Location, Water Views, AC & Steps from Inkwell Beach
Great Location, Water Views, AC & Steps from Inkwell Beach
Distance to beach: 75 yards to the Inkwell beach
5 reviews read reviews
Summer:
 $10,000/wk
Off Season:
 $8,500/wk
Oak Bluffs
ID 33204
5 BR
3 baths
Sleeps 10
AKWAABA Manor Marthas Vineyard
AKWAABA Manor Marthas Vineyard
Distance to beach: 1/10 mi to Oak Bluffs Town Beach
Off Season:
 $1,100 - $1,900/night
 $7,700 - $10,000/wk
 $15,000 - $25,000/mo
2
Oak Bluffs
ID 33370
5 BR
3 baths
Sleeps 10
CENTRAL AIR! Walk to town, Porch, 5 bedrooms & 3 bathrooms
CENTRAL AIR! Walk to town, Porch, 5 bedrooms & 3 bathrooms
Distance to beach: 15 minute walk to (5/10 of a mile) State Beach
13 reviews read reviews
Summer:
 $8,000 - $9,500/wk
Off Season:
 $5,000 - $9,000/wk
4
Oak Bluffs
ID 32791
4 BR
4 baths
Sleeps 10
AIR CONDITIONED Spacious Beach House w/Attached Studio Apt.
AIR CONDITIONED Spacious Beach House w/Attached Studio Apt.
Distance to beach: 1.8 mi To Oak Bluffs Town Beach
11 reviews read reviews
Summer:
 $3,850 - $7,700/wk
Off Season:
 $400 - $550/night
 $2,800 - $6,800/wk
3
Heart of Oak Bluffs
ID 34321
4 BR
5 ½ baths
Sleeps 10
Beautiful, Fully Renovated Gingerbread House on Ocean Park
Beautiful, Fully Renovated Gingerbread House on Ocean Park
Distance to beach: 2/10 mi to Oak Bluffs Town Beach
8 reviews read reviews
Summer:
 $10,000 - $20,000/wk
Off Season:
 $6,000 - $10,000/wk
4
Oak Bluffs
ID 35269
4 BR
3 ½ baths
Sleeps 10
Contemporary 4 BR with central AC, tennis, kayaks, bikes
Contemporary 4 BR with central AC, tennis, kayaks, bikes
Distance to beach: 3.8 mi to Oak Bluffs Town Beach
Summer:
 $4,500 - $7,500/wk
Off Season:
 $600 - $800/night
 $3,500 - $4,500/wk
Oak Bluffs
ID 37186
4 BR
3 ½ baths
Sleeps 10
Ocean View Oak Bluffs 2023 Renovation
Ocean View Oak Bluffs 2023 Renovation
Distance to beach: 3.6 mi to Oak Bluffs Town Beach and 5 min walk to Sengekontacket Pond
4 reviews read reviews
Summer:
 $6,000 - $12,000/wk
Off Season:
 $400 - $850/night
 $2,500 - $8,000/wk
5
Oak Bluffs
ID 38330
4 BR
2 baths
Sleeps 10
The Tuck at Inkwell/Walk to Oak Bluffs Town Center & Beach
The Tuck at Inkwell/Walk to Oak Bluffs Town Center & Beach
Distance to beach: 3/10 mi to Oak Bluffs Town Beach
Summer:
 $5,500 - $10,000/wk
Off Season:
 $785 - $1,140/night
 $4,000 - $6,500/wk
2
Oak Bluffs
ID 38969
4 BR
4 ½ baths
Sleeps 10
Main House Convenient Oak Bluffs Location 8019
Main House Convenient Oak Bluffs Location 8019
Distance to beach: 7/10 of a mile Oak Bluffs Town Beach
Summer:
 $13,000 - $14,500/wk
Off Season:
 $7,000 - $9,000/wk
Oak Bluffs
ID 33878
4 BR
3 baths
Sleeps 10
Amazing Gem w/AC, Guest House, Mooring & Private Sandy Beach
Amazing Gem w/AC, Guest House, Mooring & Private Sandy Beach
Distance to beach: House is on Lagoon Pond; 137 feet of private, sand
OWNER SPECIAL:
Holiday Special. Price reduction to $5,000/week through the end of the year!!
Summer:
 $13,000 - $21,000/wk
Off Season:
 $1,700 - $2,150/night
 $7,000 - $17,000/wk
Oak Bluffs
ID 33937
4 BR
2 baths
Sleeps 10
Beautiful 4 BR/2 Bath w/AC. Walk to Park, Beach, & Downtown!
Beautiful 4 BR/2 Bath w/AC. Walk to Park, Beach, & Downtown!
Distance to beach: 1/10 mi to Oak Bluffs Town Beach
1 review read review
Summer:
 $5,500 - $9,500/wk
Off Season:
 $850/night
 $4,000 - $7,000/wk
Oak Bluffs
ID 37145
4 BR
2 baths
Sleeps 10
Rest and Relax in a newly renovated home - The Doll House!
Rest and Relax in a newly renovated home - The Doll House!
Distance to beach: 2.8 mi to Oak Bluffs Town Beach
7 reviews read reviews
Summer:
 $6,000 - $14,000/wk
Off Season:
 $650 - $800/night
 $4,500 - $9,000/wk
 $18,000/mo
5
Oak Bluffs - Lagoon Pond
ID 37698
4 BR
2 ½ baths
Sleeps 10
Spacious 4-Bedroom Home in Oak Bluffs w/ Private Pool
Spacious 4-Bedroom Home in Oak Bluffs w/ Private Pool
Distance to beach: 3.3 mi to Oak Bluffs Town Beach and 3.6 mi to Owen Park Beach
2 reviews read reviews
Summer:
 $10,000 - $14,000/wk
Off Season:
 $350 - $1,500/night
 $3,500 - $10,000/wk
6
Oak Bluffs
ID 39489
3 BR
2 ½ baths
Sleeps 10
The Purple Door in Heart of OB/Close to Beaches & Town
The Purple Door in Heart of OB/Close to Beaches & Town
Distance to beach: 0.8 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
Labor Day Week/Weekend Special! Flexible Days - Fall & Winter Rental at Reduced Rates.
Summer:
 $250 - $800/night
 $6,500 - $12,000/wk
 $16,000 - $36,000/mo
Off Season:
 $250 - $800/night
 $2,500 - $8,500/wk
 $6,000 - $18,000/mo
6

Oak Bluffs vacation rentals that sleep 9

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OBT2012
ID 34157
6 BR
2 baths
Sleeps 9
Charming OB 1885 Victorian Cottage
Charming OB 1885 Victorian Cottage
Distance to beach: 0.4 mi to The Jetty Beach
Off Season:
 $5,800/wk
Vineyard Haven
ID 38413
5 BR
3 ½ baths
Sleeps 9
Charming Vineyard Haven Home near Lagoon Pond
Charming Vineyard Haven Home near Lagoon Pond
Distance to beach: Short Distance to Lagoon Pond
Summer:
 $7,000 - $9,000/wk
Oak Bluffs, Copeland Historic
ID 22456
4 BR
3 baths
Sleeps 9
Solera - Ocean Views, Steps to Inkwell Beach
Solera - Ocean Views, Steps to Inkwell Beach
Distance to beach: Inkwell Beach is 1 short block away
21 reviews read reviews
Summer:
 $8,000 - $16,500/wk
Off Season:
 $850 - $1,100/night
 $6,500 - $9,000/wk
7
Oak Bluffs
ID 31591
4 BR
2 ½ baths
Sleeps 9
Oceanfront, steps to beach, walk to town & ferry!
Oceanfront, steps to beach, walk to town & ferry!
Distance to beach: 1/10 Oak Bluffs Town Beach and Oak Bluffs Town Beach (ocean) across the street
9 reviews read reviews
OWNER SPECIAL:
Book now for summer 2025!
Summer:
 $10,000 - $17,900/wk
 $39,000 - $60,000/mo
Off Season:
 $8,000 - $12,500/wk
 $15,000 - $35,000/mo
5
Oak Bluffs
ID 29856
4 BR
3 baths
Sleeps 9
Newly Renovated! Walk to Town Oak Bluffs 4 BR/3Bath A/C
Newly Renovated! Walk to Town Oak Bluffs 4 BR/3Bath A/C
Distance to beach: 1/2 m. to State Beach and 1/2 m. to East Chop Beach
Summer:
 $7,000 - $10,000/wk
Off Season:
 $850 - $1,000/night
 $4,550 - $8,000/wk
Oak Bluffs
ID 33354
4 BR
3 baths
Sleeps 9
Enchanting Cottage with Central AC & Lagoon pond views
Enchanting Cottage with Central AC & Lagoon pond views
Distance to beach: 1.4 mi to Eastville Beach
OWNER SPECIAL:
WATERVIEWS, GREAT HOUSE; JULY 6TH,13TH & 20TH;AUGUST 17TH, 24TH, 31ST!
Summer:
 $8,500 - $11,500/wk
Off Season:
 $5,000 - $9,000/wk
Oak Bluffs
ID 36607
4 BR
1 bath
Sleeps 9
5 min walk to lagoon w/new outdoor shower
5 min walk to lagoon w/new outdoor shower
Distance to beach: 1/4 mi to Lagoon in Oak Bluffs
7 reviews read reviews
Summer:
 $3,500 - $4,500/wk
Off Season:
 $800 - $3,500/wk
Oak Bluffs
ID 38080
4 BR
4 ½ baths
Sleeps 9
East Chop, Newly Renovated 4BR, Walk to Beach & Downtown
East Chop, Newly Renovated 4BR, Walk to Beach & Downtown
Distance to beach: 1.1 mi to The Jetty Beach and 1/2 mi to Marinelli Beach East Chop
9 reviews read reviews
OWNER SPECIAL:
Multi-week discount for Summer 2025. Contact me to discuss renting for 2-3 weeks next summer.
Summer:
 $7,000 - $11,000/wk
Off Season:
 $800 - $1,000/night
 $6,000 - $8,000/wk
3
Oak Bluffs
ID 38650
4 BR
3 baths
Sleeps 9
Cozy Cottage Near Inkwell Beach (New Build)
Cozy Cottage Near Inkwell Beach (New Build)
Distance to beach: 0.5 mi to Oak Bluffs Town Beach
3 reviews read reviews
Summer:
 $6,000 - $9,000/wk
Off Season:
 $430 - $1,200/night
 $4,000 - $6,000/wk
3
Oak Bluffs
ID 39480
4 BR
2 ½ baths
Sleeps 9
Centrally Located Oak Bluffs Property next to Bike Path
Centrally Located Oak Bluffs Property next to Bike Path
Distance to beach: 4.8 mi to State Beach
Summer:
 $4,200 - $6,020/wk
Off Season:
 $600 - $860/night
 $4,200 - $6,020/wk
3
Oak Bluffs
ID 35803
4 BR
2 ½ baths
Sleeps 9
Tranquility in Oak Bluffs
Tranquility in Oak Bluffs
Distance to beach: 4.2 mi to Oak Bluffs Town Beach and 5.3 mi to State Beach
3 reviews read reviews
Off Season:
 $3,000 - $5,000/wk
Oak Bluffs
ID 35107
3 BR
3 ½ baths
Sleeps 9
HEATED POOL/2 WHIRLPOOLS, CENTRAL AC,VIEW OF VINEYARD SOUND
HEATED POOL/2 WHIRLPOOLS, CENTRAL AC,VIEW OF VINEYARD SOUND
Distance to beach: 1 mi to Jetty (Marinelli) Beach, 0.3 mi to Eastvi
OWNER SPECIAL:
Book Now BIG WEEKS OPEN FILM FESTIVAL 8/3/25 8/10/25open FIREWORKS! 8/16/25.
Summer:
 $17,000/wk
Off Season:
 $10,000 - $17,000/wk

Oak Bluffs vacation rentals that sleep 8

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Oak Bluffs
ID 21269
5 BR
1 ½ bath
Sleeps 8
5 BR, Oceanviews, Inkwell,Walk to Town, Ferry, Harbor
5 BR, Oceanviews, Inkwell,Walk to Town, Ferry, Harbor
Distance to beach: 100 Feet Oak Bluffs Town Beach and 100 feet to Inkwell Beach
OWNER SPECIAL:
GREAT WEEKS 2025! OPEN JUNE 29TH, JULY 27TH, AUGUST 10TH AND 24TH! BOOK NOW!
Summer:
 $7,000/wk
Off Season:
 $6,500 - $7,000/wk
Lagoon Pond Estates, Oak Bluff
ID 34037
5 BR
3 ½ baths
Sleeps 8
Salty Sanctuary with Deeded Access to Lagoon Pond
Salty Sanctuary with Deeded Access to Lagoon Pond
Distance to beach: 3.1 mi to Oak Bluffs Town Beach and 4.5 miles Eastville Beach
2 reviews read reviews
Summer:
 $4,800 - $6,500/wk
Off Season:
 $400 - $650/night
 $3,500 - $5,500/wk
6
Oak Bluffs
ID 25368
4 BR
3 baths
Sleeps 8
Spacious retreat, just steps to Lagoon Beach - Great Value!!
Spacious retreat, just steps to Lagoon Beach - Great Value!!
Distance to beach: Lagoon Beach, approx. 500 feet
2 reviews read reviews
OWNER SPECIAL:
Juneteenth-6/18-6/24 7 nights, pay for 6, savings of $525.
Summer:
 $535 - $635/night
 $3,750 - $4,450/wk
Off Season:
 $500 - $522/night
 $3,000 - $4,000/wk
4
Oak Bluffs
ID 12643
4 BR
2 baths
Sleeps 8
Charming, Steps to Town & Beach, Central Air
Charming, Steps to Town & Beach, Central Air
Distance to beach: 10 minute walk
13 reviews read reviews
Summer:
 $4,900 - $6,900/wk
Off Season:
 $399 - $690/night
 $2,800 - $6,300/wk
Oak Bluffs
ID 26262
4 BR
1 ½ bath
Sleeps 8
La Sirena, The Mermaid Of Oak Bluffs
La Sirena, The Mermaid Of Oak Bluffs
Distance to beach: less than a mile Oak Bluffs Town Beach
8 reviews read reviews
Summer:
 $4,800 - $5,800/wk
Off Season:
 $4,800/wk
4
Oak Bluffs
ID 29717
4 BR
2 baths
Sleeps 8
Cozy home...walk to Oak Bluffs Marina & Gingerbread Houses
Cozy home...walk to Oak Bluffs Marina & Gingerbread Houses
Distance to beach: Inkwell Beach approx. 1/2 a mile
6 reviews read reviews
Summer:
 $4,300 - $5,000/wk
Off Season:
 $600/night
 $4,300/wk
Walk to town, and beach, shops
ID 29080
4 BR
2 baths
Sleeps 8
Walk to town and beach Oak Bluffs 4 bedrooms renovated home
Walk to town and beach Oak Bluffs 4 bedrooms renovated home
Distance to beach: Oak Bluffs State Beach and 1/2 mile to Oak Bluffs town beach, East Chop beach
3 reviews read reviews
Summer:
 $3,500 - $10,000/wk
Off Season:
 $750 - $1,000/night
 $3,500 - $7,000/wk
7
Oak Bluffs
ID 28871
4 BR
2 baths
Sleeps 8
Cozy, Walk to town, 4 Bdrm, A/C Kid & Dog friendly Welcome!
Cozy, Walk to town, 4 Bdrm, A/C Kid & Dog friendly Welcome!
Distance to beach: Under 1/2 mile to Inkwell, Jetty and Pay Beach
5 reviews read reviews
Summer:
 $4,500 - $6,500/wk
Off Season:
 $4,000 - $5,500/wk
 $2,500 - $3,000/mo
6
Oak Bluffs
ID 31304
4 BR
2 baths
Sleeps 8
Classic waterfront Vict. cottage, walk to town; huge porch
Classic waterfront Vict. cottage, walk to town; huge porch
Distance to beach: Two blocks to Inkwell & OB town beach, Harthaven
18 reviews read reviews
Summer:
 $800 - $1,400/night
 $7,700 - $9,800/wk
Off Season:
 $600 - $1,200/night
 $3,500 - $7,700/wk
 $6,500/mo
3
Oak Bluffs
ID 19178
4 BR
2 baths
Sleeps 8
Renovated Victorian Home - 2 Blocks to Beach, Town & Parks
Renovated Victorian Home - 2 Blocks to Beach, Town & Parks
Distance to beach: 2 Blocks Oak Bluffs Town Beach and 2 Blocks The Jetty Beach
5 reviews read reviews
OWNER SPECIAL:
Summer 2025 is now open and ready to book. Prime weeks still available!!!
Summer:
 $3,000 - $13,000/wk
Off Season:
 $2,500 - $4,000/wk
 $2,800 - $4,000/mo
5
Oak Bluffs
ID 32817
4 BR
3 ½ baths
Sleeps 8
Exquisite family home - w/central A/C + heated pool!
Exquisite family home - w/central A/C + heated pool!
Distance to beach: 1 and 2/10 mile Oak Bluffs Town Beach and 3 miles State Beach
7 reviews read reviews
Summer:
 $7,500 - $16,500/wk
Off Season:
 $5,000 - $8,000/wk
Oak Bluffs
ID 33286
4 BR
2 baths
Sleeps 8
Lagoon Chic 4 Bedroom Family Home
Lagoon Chic 4 Bedroom Family Home
Distance to beach: 500 steps Eastville Beach and Inkwell Beach 1.2 miles
14 reviews read reviews
Summer:
 $3,500 - $4,620/wk
Off Season:
 $500/night
 $2,200 - $4,620/wk
3
Oak Bluffs
ID 31301
4 BR
2 ½ baths
Sleeps 8
Ocean Park Victorian Gem w/Sweeping Water Views
Ocean Park Victorian Gem w/Sweeping Water Views
Distance to beach: 30 yards from Oak Bluffs Town Beach and 150 yards to downtown.
1 review read review
Summer:
 $6,825 - $9,975/wk
Off Season:
 $2,500 - $8,400/wk
Meadow View Farms
ID 33786
4 BR
2 ½ baths
Sleeps 8
Peaceful Meadows
Peaceful Meadows
Distance to beach: 2.6 mi to Oak Bluffs Town Beach
8 reviews read reviews
Summer:
 $5,200/wk
Off Season:
 $2,500 - $4,500/wk
4
Oak Bluffs
ID 32868
4 BR
2 ½ baths
Sleeps 8
4 BR Home Inkwell Beach, Town, Basketball,Pickleball, Tennis
4 BR Home Inkwell Beach, Town, Basketball,Pickleball, Tennis
Distance to beach: 5 minute walk to Oak BluffsTown & Inkwell Beaches
OWNER SPECIAL:
BEST WEEKS OF SUMMER 2025 GOING FAST! ALL OF JUNE 28TH, JULY 5TH,12TH, & AUGUST 16TH,23RD,30TH!
Summer:
 $8,500 - $9,500/wk
Off Season:
 $7,500 - $8,500/wk
Oak Bluffs
ID 28167
4 BR
3 ½ baths
Sleeps 8
Waterview Farms, Prime Bike Trails, Martha's Vineyard
Waterview Farms, Prime Bike Trails, Martha's Vineyard
Distance to beach: Water View Farms Landing
Summer:
 $4,000 - $5,500/wk
Off Season:
 $4,000 - $5,500/wk
Oak Bluffs
ID 34079
4 BR
4 baths
Sleeps 8
Beautiful 4 BR/4 BA Modern Victorian: The Mack on Winemack
Beautiful 4 BR/4 BA Modern Victorian: The Mack on Winemack
Distance to beach: 1.1 mi to The Jetty Beach and 1.3 to Inkwell Beach
14 reviews read reviews
Summer:
 $3,500 - $9,500/wk
Off Season:
 $2,500 - $4,500/wk
6
Oak Bluffs
ID 32194
4 BR
3 baths
Sleeps 8
Historical J. A. Norton House
Historical J. A. Norton House
Distance to beach: 1/10 mile Oak Bluffs Town Beach and 1 mile State Beach (Joseph Sylvia State Beach)
Summer:
 $8,800 - $10,000/wk
Off Season:
 $4,300 - $8,500/wk
Oak Bluffs
ID 26201
4 BR
2 baths
Sleeps 8
Charming Cape near Lagoon and Town
Charming Cape near Lagoon and Town
Distance to beach: 3 Miles State Beach and 1 Mile Eastville Beach
Summer:
 $3,000/wk
Off Season:
 $400 - $600/night
 $3,000/wk
Oak Bluffs
ID 35109
4 BR
3 ½ baths
Sleeps 8
Luxury Getaway At The Preserve
Luxury Getaway At The Preserve
Distance to beach: 2.5 mi to Oak Bluffs Town Beach
Summer:
 $18,000 - $24,500/wk
Off Season:
 $19,000/wk
3
Oak Bluffs
ID 35166
4 BR
2 ½ baths
Sleeps 8
Fully Renovated Victorian 4 Br /2.5 Baths Steps To Inkwell
Fully Renovated Victorian 4 Br /2.5 Baths Steps To Inkwell
Distance to beach: 0.1 mi to Oak Bluffs Town Beach
7 reviews read reviews
Summer:
 $7,000 - $9,000/wk
Off Season:
 $500 - $1,000/night
 $3,500 - $7,500/wk
5
East Chop
ID 33664
4 BR
3 baths
Sleeps 8
CENTRAL AC,4 BR,EASTCHOP, EASTVILLE BEACH AUGUST OPEN!
CENTRAL AC,4 BR,EASTCHOP, EASTVILLE BEACH AUGUST OPEN!
Distance to beach: 8/10 mi to The Jetty Beach
OWNER SPECIAL:
ALL OF AUGUST 2025 IS OPEN, BOOK NOW , BEST WEEKS OF THE SEASON !
Summer:
 $7,500 - $10,500/wk
Off Season:
 $7,500 - $8,750/wk
Oak Bluffs
ID 35279
4 BR
2 ½ baths
Sleeps 8
Your Own Peaceful Getaway w/AC in Oak Bluffs (Sorry No Pets)
Your Own Peaceful Getaway w/AC in Oak Bluffs (Sorry No Pets)
Distance to beach: 1.5 mi to Oak Bluffs Town Beach
6 reviews read reviews
Summer:
 $6,500 - $8,000/wk
Off Season:
 $4,500 - $6,500/wk
4
Oak Bluffs
ID 35483
4 BR
1 ½ bath
Sleeps 8
La Bella Sorella (The Beautiful Sister)
La Bella Sorella (The Beautiful Sister)
Distance to beach: 4/10 mi to Oak Bluffs Town Beach
3 reviews read reviews
Summer:
 $5,800 - $6,800/wk
Off Season:
 $5,800/wk
3
Oak Bluffs
ID 36320
4 BR
3 baths
Sleeps 8
Bright and Airy Oasis in OB
Bright and Airy Oasis in OB
Distance to beach: 1 mile Oak Bluffs Town Beach
6 reviews read reviews
Off Season:
 $700/night
 $4,900/wk
2
Oak Bluffs
ID 27205
4 BR
4 ½ baths
Sleeps 8
Contemporary Home with Heated Pool/Spa - Pay No Room Tax
Contemporary Home with Heated Pool/Spa - Pay No Room Tax
Distance to beach: Inkwell Beach is 1.5 miles away
Summer:
 $18,000/wk
Oak Bluffs
ID 36488
4 BR
2 ½ baths
Sleeps 8
Gingerbread Cottage with Amazing Oak Bluffs Harbor View
Gingerbread Cottage with Amazing Oak Bluffs Harbor View
Distance to beach: 4/10 mi to Oak Bluffs Town Beach and 5/10 mi to The Jetty Beach
Summer:
 $7,250 - $7,700/wk
Off Season:
 $7,000 - $7,500/wk
Oak Bluffs
ID 34260
4 BR
2 ½ baths
Sleeps 8
Great central location, Central AC
Great central location, Central AC
Distance to beach: 4.0 mi to Oak Bluffs Town Beach
Summer:
 $7,500 - $8,900/wk
Off Season:
 $1,000 - $1,200/night
 $7,000 - $8,000/wk
Oak Bluffs
ID 31476
4 BR
2 baths
Sleeps 8
Fun, Family, Vineyard Getaway
Fun, Family, Vineyard Getaway
Distance to beach: Lagoon 0.3 mi, State beach 1.5 mi
1 review read review
Off Season:
 $370 - $500/night
 $3,000/wk
4
Sengekontacket Association, Oa
ID 37096
4 BR
2 baths
Sleeps 8
Sun Filled Waterfront Home with a Beautiful Pond View
Sun Filled Waterfront Home with a Beautiful Pond View
Distance to beach: 3.6 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
Rate posted is now $900 OFF of August dates.FERRY Tickets may be available if you contact owner.
Summer:
 $6,000 - $8,000/wk
Off Season:
 $3,000 - $7,500/wk
Oak Bluffs
ID 37238
4 BR
1 ½ bath
Sleeps 8
Victorian Beach Rental with Ocean Views, Wrap-around Porch
Victorian Beach Rental with Ocean Views, Wrap-around Porch
Distance to beach: 489 ft to Oak Bluffs Town Beach
1 review read review
Summer:
 $5,000/wk
Off Season:
 $2,500 - $4,000/wk
Oak Bluffs
ID 35412
4 BR
2 ½ baths
Sleeps 8
Charming 19Th Century Victorian Cottage In Oak Bluffs
Charming 19Th Century Victorian Cottage In Oak Bluffs
Distance to beach: 0.5 mi to The Jetty Beach and 0.8 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
BOOKING NOW FOR JUNTEENTH AND JULY WEEKS 2025! GREAT RATES!
Summer:
 $5,500 - $6,000/wk
Off Season:
 $5,500 - $6,000/wk
Oak Bluffs
ID 37469
4 BR
2 baths
Sleeps 8
Classic Victorian Beauty Steps to Beach
Classic Victorian Beauty Steps to Beach
Distance to beach: 0.1 mi to Oak Bluffs Town Beach and Inkwell Beach
Summer:
 $6,000 - $9,000/wk
Off Season:
 $750 - $1,200/night
 $6,000/wk
Oak Bluffs
ID 37484
4 BR
2 baths
Sleeps 8
Nashawena Park Home- Close to Inkwell and town
Nashawena Park Home- Close to Inkwell and town
Distance to beach: 4/10 mi to Oak Bluffs Town Beach
Summer:
 $7,000 - $11,500/wk
Off Season:
 $500 - $1,000/night
 $7,000 - $8,000/wk
3
Oak Bluffs
ID 38145
4 BR
3 baths
Sleeps 8
Hideaway At Meadow View Farm/Private Tennis Courts
Hideaway At Meadow View Farm/Private Tennis Courts
Distance to beach: 2.9 mi to Oak Bluffs Town Beach
5 reviews read reviews
Summer:
 $5,600 - $7,000/wk
Off Season:
 $430/night
 $3,000 - $7,000/wk
5
Oak Bluffs
ID 38181
4 BR
2 baths
Sleeps 8
Quintessential East Chop Cottage - with A/C
Quintessential East Chop Cottage - with A/C
Distance to beach: 0.6 mi to The Jetty Beach
2 reviews read reviews
OWNER SPECIAL:
Book now for Summer 2025.
Summer:
 $4,600 - $6,500/wk
Off Season:
 $700/night
 $4,000 - $5,200/wk
Oak Bluffs
ID 38312
4 BR
2 ½ baths
Sleeps 8
Spacious Oak Bluffs Farmhouse
Spacious Oak Bluffs Farmhouse
Distance to beach: 2.6 mi to Oak Bluffs Town Beach
1 review read review
Summer:
 $5,000 - $7,000/wk
Off Season:
 $2,500 - $5,000/wk
 $3,500 - $5,500/mo
3
Oak Bluffs
ID 38862
4 BR
2 baths
Sleeps 8
Relaxing Oak Bluffs Getaway with A/C, Close to Town
Relaxing Oak Bluffs Getaway with A/C, Close to Town
Distance to beach: 0.9 mi to Oak Bluffs Town Beach
2 reviews read reviews
Summer:
 $3,600 - $5,700/wk
Off Season:
 $3,000 - $3,600/wk
1
Oak Bluffs
ID 38989
4 BR
3 ½ baths
Sleeps 8
Fabulous New 4 Bedroom in Oak Bluffs
Fabulous New 4 Bedroom in Oak Bluffs
Distance to beach: 1.6 mi to The Jetty Beach
Summer:
 $5,200 - $7,200/wk
Off Season:
 $500 - $850/night
 $3,200 - $6,400/wk
2
Oak Bluffs
ID 38972
4 BR
3 baths
Sleeps 8
4 BR, BIKE PATH, AC, FARM NECK, NEW DECOR
4 BR, BIKE PATH, AC, FARM NECK, NEW DECOR
Distance to beach: 1.3 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
Great weeks in June and July 2025!
Summer:
 $7,000 - $12,500/wk
Off Season:
 $7,000/wk
Oak Bluffs
ID 38738
4 BR
2 ½ baths
Sleeps 8
Harper House - Waterfront Luxury Rental
Harper House - Waterfront Luxury Rental
Distance to beach: 1/2 mi to Eastville Beach
1 review read review
Summer:
 $3,500 - $4,000/night
 $30,000/wk
 $120,000 - $130,000/mo
Off Season:
 $2,200 - $2,500/night
 $14,000/wk
 $72,000 - $120,000/mo
Oak Bluffs
ID 39256
4 BR
4 ½ baths
Sleeps 8
Luxurious Oak Bluffs Contemporary With Water Views
Luxurious Oak Bluffs Contemporary With Water Views
Distance to beach: 3.6 mi to Oak Bluffs Town Beach
Summer:
 $11,000 - $13,000/wk
Off Season:
 $785 - $1,000/night
 $5,500 - $10,000/wk
Oak Bluffs
ID 39277
4 BR
2 baths
Sleeps 8
Spacious Colonial Summer Home
Spacious Colonial Summer Home
Distance to beach: .7 mi to The Jetty Beach
Summer:
 $2,950 - $5,300/wk
Off Season:
 $350 - $450/night
 $1,500 - $4,000/wk
East Chop Highlands
ID 39326
4 BR
2 baths
Sleeps 8
Cozy Cottage at Coleman Corners/Walk to Beach
Cozy Cottage at Coleman Corners/Walk to Beach
Distance to beach: 1/2 mi to The Jetty Beach
10 reviews read reviews
Summer:
 $3,500 - $4,000/wk
Off Season:
 $3,200 - $3,850/wk
3
The Historic Copeland District
ID 39629
4 BR
3 ½ baths
Sleeps 8
4 BR WALK TO INKWELL, TOWN, FERRY; AC
4 BR WALK TO INKWELL, TOWN, FERRY; AC
Distance to beach: 0.3 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
"New to the Market, Inkwell beach, Waban Park, close to town Hurray Book Now !
Summer:
 $14,900 - $20,000/wk
Off Season:
 $11,000 - $14,900/wk
Oak Bluffs
ID 39688
4 BR
2 baths
Sleeps 8
Vineyard Hills Beauty
Vineyard Hills Beauty
Distance to beach: 2.8 mi to Oak Bluffs Town Beach
Summer:
 $5,500 - $8,000/wk
Off Season:
 $500 - $1,000/night
 $4,500 - $6,000/wk
Oak Bluffs
ID 12116
4 BR
2 baths
Sleeps 8
Cape Style Home - has A/C ! short walk to Lagoon Beach
Cape Style Home - has A/C ! short walk to Lagoon Beach
Distance to beach: 4 minute walk to Lagoon Beach
6 reviews read reviews
Summer:
 $4,350/wk
Off Season:
 $2,000 - $4,350/wk
Oak Bluffs
ID 19225
4 BR
2 baths
Sleeps 8
OAK BLUFFS GETAWAY!
OAK BLUFFS GETAWAY!
Distance to beach: 1.1 mile to Inkwell Beach
16 reviews read reviews
Off Season:
 $5,000/wk
Oak Bluffs
ID 19626
4 BR
1 bath
Sleeps 8
5 Minute Walk to Oak Bluffs & Jetty Beach!
5 Minute Walk to Oak Bluffs & Jetty Beach!
Distance to beach: Jetty Beach
14 reviews read reviews
Off Season:
 $275 - $775/night
 $3,000 - $3,200/wk
4
Oak Bluffs
ID 9007
4 BR
3 ½ baths
Sleeps 8
Spacious Contemporary Cape in Private Cul de Sac
Spacious Contemporary Cape in Private Cul de Sac
Distance to beach: Ink Well 5 miles, State Beach 6, VH beaches 4
6 reviews read reviews
Summer:
 $5,300 - $6,300/wk
Off Season:
 $2,500 - $6,300/wk
East Chop
ID 28974
4 BR
2 baths
Sleeps 8
Adorable Oak Bluffs Cottage with AC on East Chop
Adorable Oak Bluffs Cottage with AC on East Chop
Distance to beach: 1/2 mile to Eastville Beach
6 reviews read reviews
Summer:
 $4,200 - $4,550/wk
Off Season:
 $500/night
 $3,500 - $4,200/wk
4
Oak Bluffs - Meadow View Farms
ID 29775
4 BR
4 ½ baths
Sleeps 8
Flexible turnover days for remaining July 2024 weeks!
Flexible turnover days for remaining July 2024 weeks!
Distance to beach: State Beach - 2 miles
30 reviews read reviews
Summer:
 $4,500 - $6,900/wk
Off Season:
 $3,500 - $6,900/wk
5
Oak Bluffs
ID 30502
4 BR
2 ½ baths
Sleeps 8
Spacious, Relaxing & Central Location!
Spacious, Relaxing & Central Location!
Distance to beach: 7-10 Minute Drive to OB & Edgartown Beaches
4 reviews read reviews
Off Season:
 $6,200 - $6,500/wk
Oak Bluffs
ID 30339
4 BR
2 baths
Sleeps 8
Classic 4 B Cape in Eastville-Central AC & Heat!
Classic 4 B Cape in Eastville-Central AC & Heat!
Distance to beach: 1.5 miles Oak Bluffs Town Beach
8 reviews read reviews
Off Season:
 $2,800 - $5,000/wk
4
Oak Bluffs
ID 32448
4 BR
2 ½ baths
Sleeps 8
Walk to Town/Walk to Beach in quiet location in OB (with AC)
Walk to Town/Walk to Beach in quiet location in OB (with AC)
Distance to beach: 3 blocks to Oak Bluffs Town Beach
4 reviews read reviews
Summer:
 $6,000 - $10,000/wk
Off Season:
 $5,250 - $7,000/wk
4
Oak Bluffs - Near Farm Neck
ID 37842
4 BR
2 baths
Sleeps 8
Tree House Oak Bluffs
Tree House Oak Bluffs
Distance to beach: 1.7 mi to Oak Bluffs Town Beach
2
Oak Bluffs
ID 35115
3 BR
3 ½ baths
Sleeps 8
Experience A Luxury Getaway By The Lagoon
Experience A Luxury Getaway By The Lagoon
Distance to beach: 0.3 mi to Oak Bluffs Town Beach
Summer:
 $6,650 - $13,500/wk
Off Season:
 $3,500 - $8,000/wk
2
Historic Copeland District
ID 35575
3 BR
2 ½ baths
Sleeps 8
The Cinderella Cottage Oak Bluffs
The Cinderella Cottage Oak Bluffs
Distance to beach: 0.2 mi to Oak Bluffs Town Beach and Steps to Inkwell Beach
Summer:
 $5,500 - $11,000/wk
Off Season:
 $1,000 - $2,000/night
 $9,000/wk
5
Oak Bluffs
ID 36518
3 BR
2 baths
Sleeps 8
East Chop Waterview - Delightful Contemporary
East Chop Waterview - Delightful Contemporary
Distance to beach: 0.9 mi to The Jetty Beach
Summer:
 $6,500 - $8,000/wk
Off Season:
 $6,500 - $8,000/wk
Oak Bluffs
ID 35791
3 BR
2 ½ baths
Sleeps 8
3 BR Cottage, Town, Beaches, Ferry, Harbor, AC
3 BR Cottage, Town, Beaches, Ferry, Harbor, AC
Distance to beach: 0.4 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
Now booking for 2025!
Summer:
 $6,800 - $9,500/wk
Off Season:
 $6,800 - $7,800/wk
Oak Bluffs
ID 31215
3 BR
2 baths
Sleeps 8
Happy house 0.5mi Nancy’s & Jetty Beach: 1 2025 wk left!
Happy house 0.5mi Nancy’s & Jetty Beach: 1 2025 wk left!
Distance to beach: 1/2 Mile - Jetty beach on East Chop
1 review read review
Summer:
 $3,500 - $5,500/wk
Off Season:
 $2,800/wk
Oak Bluffs
ID 38157
3 BR
2 baths
Sleeps 8
Endless Summer Vacation
Endless Summer Vacation
Distance to beach: 0.7 mi to The Jetty Beach and 1 mile to Inkwell Beach
5 reviews read reviews
Summer:
 $4,000 - $7,500/wk
Off Season:
 $500 - $1,000/night
 $4,000 - $5,500/wk
Town
ID 38903
3 BR
2 baths
Sleeps 8
The Jessie Lee Harris Legacy House
The Jessie Lee Harris Legacy House
Distance to beach: 1.1 mi to Oak Bluffs Town Beach
Summer:
 $4,000 - $10,000/wk
Off Season:
 $3,000 - $6,000/wk
Oak Bluffs
ID 39654
3 BR
2 baths
Sleeps 8
NOBLE HOUSE: Charming Oasis Near Town & Beach
NOBLE HOUSE: Charming Oasis Near Town & Beach
Distance to beach: 1.2 mi to Oak Bluffs Town Beach
Summer:
 $6,000 - $8,500/wk
 $28,000 - $32,000/mo
Off Season:
 $900 - $8,000/wk
 $2,500 - $20,000/mo
3
Oak Bluffs
ID 30781
3 BR
2 ½ baths
Sleeps 8
Hidden Treasure: Contemporary 3 BR Home w/Access to Tennis
Hidden Treasure: Contemporary 3 BR Home w/Access to Tennis
Distance to beach: Equidistant to OB, State, VH & Edgartown Beaches
3 reviews read reviews
Summer:
 $6,500 - $9,500/wk
Off Season:
 $500 - $800/night
 $4,000 - $6,500/wk
East Chop
ID 37607
3 BR
2 baths
Sleeps 8
Booming Ben: Air-conditioned East Chop Gingerbread Cottage
Booming Ben: Air-conditioned East Chop Gingerbread Cottage
Distance to beach: 3/10 mi to The Jetty Beach
6 reviews read reviews
Summer:
 $6,500 - $8,500/wk
Off Season:
 $895 - $995/night
 $4,500 - $6,500/wk

Oak Bluffs vacation rentals that sleep 7

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Oak Bluffs
ID 6969
4 BR
2 ½ baths
Sleeps 7
Hillside Harborview
Hillside Harborview
Distance to beach: 3/10th of a mile Oak Bluffs Town Beach and 3/10 of a mile to East Chop Beach
2 reviews read reviews
Summer:
 $2,200 - $4,300/wk
Off Season:
 $2,200/wk
East Chop
ID 35529
4 BR
1 ½ bath
Sleeps 7
Quiet, Comfy Home in Heart of East Chop - walk to the beach!
Quiet, Comfy Home in Heart of East Chop - walk to the beach!
Distance to beach: 0.5 mi to The Jetty Beach
7 reviews read reviews
Summer:
 $3,500 - $5,000/wk
 $15,000 - $16,000/mo
Off Season:
 $3,000 - $3,900/wk
3
Oak Bluffs
ID 6897
3 BR
1 ½ bath
Sleeps 7
Comfortable Cape within walking distance to Downtown
Comfortable Cape within walking distance to Downtown
Distance to beach: 8/10 miles to Oak Bluffs Town Beach
8 reviews read reviews
Summer:
 $3,200/wk
Off Season:
 $2,800/wk
Historic Downtown Copeland Dis
ID 13640
3 BR
2 ½ baths
Sleeps 7
Lovely In-town Victorian ~ walk to beach & ferry
Lovely In-town Victorian ~ walk to beach & ferry
Distance to beach: 2.5 blocks to Oak Bluffs Town Beach and the Inkwell
14 reviews read reviews
Summer:
 $3,600 - $4,000/wk
Off Season:
 $3,100 - $3,400/wk
6
Oak Bluffs
ID 21147
3 BR
2 baths
Sleeps 7
Oak Bluffs ''Quaint Victorian Home''
Oak Bluffs ''Quaint Victorian Home''
Distance to beach: One and a quarter mile State Beach and 1/4 mile, Eastville--1 1/2 Oak Bluffs town beach
4 reviews read reviews
Summer:
 $2,600 - $4,000/wk
 $13,000 - $16,000/mo
Off Season:
 $350 - $500/night
 $2,400 - $3,800/wk
 $8,000 - $12,000/mo
5
Historic Copeland District/ In
ID 28831
3 BR
2 ½ baths
Sleeps 7
Perfect! 7 houses from the Beach-Walk to Ferry & Town!
Perfect! 7 houses from the Beach-Walk to Ferry & Town!
Distance to beach: 500 ft to Town Beach, Inkwell, State Beach
2 reviews read reviews
Summer:
 $6,000 - $9,000/wk
Off Season:
 $2,500 - $6,000/wk
Oak Bluffs
ID 33550
3 BR
3 baths
Sleeps 7
Our great Guest Review's tell it all!
Our great Guest Review's tell it all!
Distance to beach: 2 miles Oak Bluffs Town Beach and 1.5 Eastville Beach
26 reviews read reviews
Summer:
 $6,300 - $7,500/wk
Off Season:
 $5,300 - $6,100/wk
7
East Chop
ID 33916
3 BR
2 baths
Sleeps 7
East Chop Home w/Central AC on a Quiet Street
East Chop Home w/Central AC on a Quiet Street
Distance to beach: 7/10 mi to The Jetty Beach
Summer:
 $6,500 - $8,500/wk
Off Season:
 $5,000/wk
Oak Bluffs-MCVMA
ID 35732
3 BR
1 ½ bath
Sleeps 7
OB Harbor-Front Ginger-Bread Cottage ''Tight Squeeze''
OB Harbor-Front Ginger-Bread Cottage ''Tight Squeeze''
Distance to beach: 4/10 mi to Oak Bluffs Town Beach and 5/10 mi to The Jetty Beach
6 reviews read reviews
Summer:
 $4,950 - $6,995/wk
Off Season:
 $3,950 - $4,950/wk
4
Lagoon
ID 38690
3 BR
2 baths
Sleeps 7
Waterfront Home With Private Beach in Oak Bluffs
Waterfront Home With Private Beach in Oak Bluffs
Distance to beach: 2.4 mi Oak Bluffs Town Beach and 100 ft to Private beach downhill on a path
Summer:
 $7,500 - $12,000/wk
Off Season:
 $3,500 - $7,500/wk
Oak Bluffs
ID 39425
2 BR
2 baths
Sleeps 7
Oceanfront on OB Lagoon; Direct Access to Beach; 2 Moorings
Oceanfront on OB Lagoon; Direct Access to Beach; 2 Moorings
Distance to beach: On Oak Bluffs Lagoon
Summer:
 $7,500 - $11,000/wk
Off Season:
 $2,000 - $8,400/night
 $7,000 - $10,000/wk
4
Oak Bluffs
ID 28887
2 BR
1 ½ bath
Sleeps 7
2+BR ''Gingerbread'' Cottage - Walk to ALL!
2+BR ''Gingerbread'' Cottage - Walk to ALL!
Distance to beach: 10 minute walk to Oak Bluffs Town Beach and 10 minute walk to The Jetty Beach
14 reviews read reviews
Summer:
 $3,700 - $4,800/wk
Off Season:
 $2,100 - $3,700/wk
3

Oak Bluffs vacation rentals that sleep 6

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Oak Bluffs
ID 29086
4 BR
2 baths
Sleeps 6
Quaint Historic Cottage: Walk to Beach, Harbor, Circuit Ave
Quaint Historic Cottage: Walk to Beach, Harbor, Circuit Ave
Distance to beach: 1/4 mile The Jetty Beach and 1/2 mile Oak Bluffs Town Beach
3 reviews read reviews
Summer:
 $5,000 - $9,700/wk
 $38,000 - $39,000/mo
Off Season:
 $5,000 - $7,000/wk
 $20,000 - $28,000/mo
3
Oak Bluffs
ID 9098
3 BR
2 baths
Sleeps 6
Waterfront Cottage on Oak Bluffs Harbor w/ Small Beach!
Waterfront Cottage on Oak Bluffs Harbor w/ Small Beach!
Distance to beach: 5 min walk The Jetty Beach and On harbor w/sandy beach; 5 min walk to ocean beach
15 reviews read reviews
Summer:
 $5,250 - $7,875/wk
Off Season:
 $4,900 - $5,250/wk
Sea View Ave. just out of town
ID 19701
3 BR
2 baths
Sleeps 6
Charming 1800's Victorian Cottage Fronting the Sound
Charming 1800's Victorian Cottage Fronting the Sound
Distance to beach: 500 feet to inkwell beach
11 reviews read reviews
Summer:
 $4,000 - $5,200/wk
Off Season:
 $4,500/wk
2
Oak Bluffs
ID 22799
3 BR
3 baths
Sleeps 6
MV Peace of Pie - Short 15 min walk to OB center, AC
MV Peace of Pie - Short 15 min walk to OB center, AC
Distance to beach: 1.1 miles to Oak Bluffs Town Beach
15 reviews read reviews
Summer:
 $5,000 - $6,000/wk
Off Season:
 $4,500 - $5,000/wk
Oak Bluffs Lagoon Pond area
ID 23542
3 BR
2 baths
Sleeps 6
Contemporary 3 BR Just 300 Yds from the Lagoon in Oak Bluffs
Contemporary 3 BR Just 300 Yds from the Lagoon in Oak Bluffs
Distance to beach: Lagoon Beach 1/2 mile, Eastville Beach < 1 mile
10 reviews read reviews
Summer:
 $3,200 - $3,700/wk
Off Season:
 $3,600/wk
6
Oak Bluffs
ID 20575
3 BR
3 baths
Sleeps 6
Bright Modern House w/ AC-Sleeps 7 Walk to Beach & Shops
Bright Modern House w/ AC-Sleeps 7 Walk to Beach & Shops
Distance to beach: Lagoon Beach-end of block;15 min bike- State Beach
2 reviews read reviews
Summer:
 $3,000 - $4,900/wk
 $15,000 - $18,000/mo
Off Season:
 $4,200 - $4,900/wk
 $3,500 - $9,000/mo
Oak Bluffs
ID 24822
3 BR
2 baths
Sleeps 6
Pristine Retreat - Blue Stone Patio - Fire Pit
Pristine Retreat - Blue Stone Patio - Fire Pit
Distance to beach: 3 miles Oak Bluffs Town Beach and Less than 2 miles to Sailing Camp Park
28 reviews read reviews
Summer:
 $5,600 - $7,400/wk
Off Season:
 $4,200 - $5,600/wk
6
Oak Bluffs
ID 19888
3 BR
3 baths
Sleeps 6
Beautiful Sunny w/Lagoon View-Walk to Center of Oak Bluffs
Beautiful Sunny w/Lagoon View-Walk to Center of Oak Bluffs
Distance to beach: 130 feet (steps) from the house
5 reviews read reviews
Summer:
 $2,100 - $3,600/wk
 $2,650 - $13,000/mo
Off Season:
 $1,800 - $2,600/wk
 $1,800 - $9,000/mo
32 County Road, Oak Bluffs
ID 31344
3 BR
2 baths
Sleeps 6
OB-POSH with Central A/C Owner has ferry tix except 7/9-16
OB-POSH with Central A/C Owner has ferry tix except 7/9-16
Distance to beach: Eastville Beach about 1/2 a mile
Summer:
 $4,000 - $8,450/wk
Off Season:
 $4,000 - $6,900/wk
2
Oak Bluffs
ID 33125
3 BR
2 baths
Sleeps 6
Cozy Sunlit Cottage, quick walk to downtown Oak Bluffs!
Cozy Sunlit Cottage, quick walk to downtown Oak Bluffs!
Distance to beach: 1 mile To Oak Bluffs Town Beach
6 reviews read reviews
Summer:
 $2,800 - $3,300/wk
Off Season:
 $2,800/wk
Near MV Hospital
ID 33461
3 BR
1 bath
Sleeps 6
3 Bedrooms on OB's Towanticut St. New living room furnIture.
3 Bedrooms on OB's Towanticut St. New living room furnIture.
Distance to beach: 7/10 mi to The Jetty Beach and 1/2 mi to Eastville Beach
Summer:
 $2,850 - $3,150/wk
Off Season:
 $2,250 - $3,150/wk
East Chop
ID 32946
3 BR
2 baths
Sleeps 6
Newly Renovated East Chop Home. Walk to beach and town!
Newly Renovated East Chop Home. Walk to beach and town!
Distance to beach: 3/10 mi To The Jetty Beach
17 reviews read reviews
Summer:
 $4,500 - $5,500/wk
Off Season:
 $3,500 - $4,500/wk
5
Walk to town- quiet location
ID 33701
3 BR
2 baths
Sleeps 6
Quiet Oak Bluffs Neighborhood walk to Harbor, Beach,Village
Quiet Oak Bluffs Neighborhood walk to Harbor, Beach,Village
Distance to beach: 6/10 mi to The Jetty Beach and 1 mi Oak Bluffs Town Beach
Summer:
 $3,000 - $3,800/wk
Off Season:
 $2,800 - $3,800/wk
 $3,000 - $3,500/mo
Oak Bluffs
ID 34492
3 BR
2 ½ baths
Sleeps 6
Heated saltwater pool, stunning sunsets, 2 kayaks!
Heated saltwater pool, stunning sunsets, 2 kayaks!
Distance to beach: 3/10 mi to Lagoon Pond Public Beach Oak Bluffs Town Beach
20 reviews read reviews
Summer:
 $7,900 - $11,600/wk
Off Season:
 $850 - $1,000/night
 $5,500 - $8,600/wk
 $17,000/mo
5
Oak Bluffs
ID 34180
3 BR
2 baths
Sleeps 6
A/C, Assoc.tennis courts & dock, some confirmed RT FERRY TIX
A/C, Assoc.tennis courts & dock, some confirmed RT FERRY TIX
Distance to beach: 3 & 4/10 mi Oak Bluffs Town Beach and 5 miles State Beach
2 reviews read reviews
Summer:
 $2,800 - $8,000/wk
Off Season:
 $2,450 - $3,750/wk
Oak Bluffs
ID 35304
3 BR
3 ½ baths
Sleeps 6
LOVELY 3 BR, CENTRAL AC, MEDIA & GAME ROOM, LAGOON
LOVELY 3 BR, CENTRAL AC, MEDIA & GAME ROOM, LAGOON
Distance to beach: 1.9 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
2025 WEEKS ARE STILL AVAILABE FOR JULY BOOK NOW BEFORE THEY GO !
Summer:
 $7,500 - $9,500/wk
Off Season:
 $7,500 - $8,500/wk
Oak Bluffs
ID 34548
3 BR
2 baths
Sleeps 6
Jupiter House: Recently Renovated, Open-concept 3 BR Home
Jupiter House: Recently Renovated, Open-concept 3 BR Home
Distance to beach: 1.5 miles to Oak Bluffs Town Beach and 0.5 miles to Eastville Beach
3 reviews read reviews
Summer:
 $3,000 - $4,700/wk
Off Season:
 $500/night
 $3,000 - $3,200/wk
7
Oak Bluffs
ID 36742
3 BR
2 baths
Sleeps 6
Beautiful Inground Pool, Central Location
Beautiful Inground Pool, Central Location
Distance to beach: 4.4 miles Oak Bluffs Town Beach
1 review read review
Summer:
 $5,400 - $6,500/wk
Off Season:
 $2,000 - $5,700/wk
Oak Bluffs
ID 34650
3 BR
1 bath
Sleeps 6
3 BR, LAGOON POND, BIKE PATH, BEAUTIFUL SUNSETS!
3 BR, LAGOON POND, BIKE PATH, BEAUTIFUL SUNSETS!
Distance to beach: on private beach; 1.6 m to Oak Bluffs Town Beach
OWNER SPECIAL:
BEST WEEKS OF THE SEASON; AUGUST 2ND, 10TH AND 17th 2025! BOOK NOW BEFORE THEY GO!
Summer:
 $8,200 - $11,500/wk
Off Season:
 $8,200/wk
Oak Bluffs
ID 35664
3 BR
3 baths
Sleeps 6
Perfect Family House - Walk to Lagoon
Perfect Family House - Walk to Lagoon
Distance to beach: 2 blks to Lagoon Pond;1mi to Oak Bluffs Town Beach
2 reviews read reviews
Summer:
 $3,000 - $5,000/wk
Off Season:
 $500/night
 $1,800 - $4,000/wk
2
Oak Bluffs
ID 37961
3 BR
2 baths
Sleeps 6
Beautiful Home / Walk to Town
Beautiful Home / Walk to Town
Distance to beach: 1.0 mi to Oak Bluffs Town Beach
Off Season:
 $550/night
 $3,000 - $3,850/wk
 $15,000 - $16,000/mo
Oak Bluffs
ID 38381
3 BR
1 ½ bath
Sleeps 6
History and Heritage Awaits/Walk to Beach
History and Heritage Awaits/Walk to Beach
Distance to beach: 0.5 mi to The Jetty Beach
Summer:
 $2,000 - $4,000/wk
 $16 - $15,500/mo
Off Season:
 $600 - $3,500/wk
 $2,500 - $11,000/mo
4
Gingerbred Cottages - MVCMA
ID 38584
3 BR
1 ½ bath
Sleeps 6
Beautifully Updated Gingerbread Family Cottage Walk to Town
Beautifully Updated Gingerbread Family Cottage Walk to Town
Distance to beach: 0.5 mi to Oak Bluffs Town Beach
Summer:
 $5,250 - $5,500/wk
5
Oak Bluffs
ID 38623
3 BR
1 bath
Sleeps 6
Dottie's House - HIstoric Home in the Heart of Oak Bluffs
Dottie's House - HIstoric Home in the Heart of Oak Bluffs
Distance to beach: 1/2 mi to The Jetty Beach and 1.2 mi to Oak Bluffs Town Beach
4 reviews read reviews
Summer:
 $3,300 - $5,500/wk
Off Season:
 $450 - $550/night
 $3,150 - $4,200/wk
Oak Bluffs
ID 38836
3 BR
1 ½ bath
Sleeps 6
Oak Bluffs Victorian Gingerbread Cottage
Oak Bluffs Victorian Gingerbread Cottage
Distance to beach: 0.2 mi to Oak Bluffs Town Beach
OWNER SPECIAL:
Great weeks of summer, going fast! June 13th, June 20th and August 24th 2025.
Summer:
 $5,500 - $6,500/wk
Off Season:
 $6,500/wk
Oak Bluffs
ID 39435
3 BR
1 ½ bath
Sleeps 6
Updated Home, Steps to Town/Ferry, Beach, Ocean Views
Updated Home, Steps to Town/Ferry, Beach, Ocean Views
Distance to beach: 300 yards Oak Bluffs Town Beach
3 reviews read reviews
Summer:
 $6,000 - $8,500/wk
Off Season:
 $300 - $600/night
 $2,800 - $7,000/wk
2
Oak Bluffs
ID 39601
3 BR
2 baths
Sleeps 6
Pet Friendly 3BR Home Close to Town and Beach in Oak Bluffs
Pet Friendly 3BR Home Close to Town and Beach in Oak Bluffs
Distance to beach: 1.3 mi to Oak Bluffs Town Beach
Summer:
 $4,500 - $8,000/wk
Off Season:
 $4,500/wk
4
Oak Bluffs - East Chop
ID 39616
3 BR
3 baths
Sleeps 6
Oak Bluffs/East Chop Modern Retreat w/ Detached Studio!
Oak Bluffs/East Chop Modern Retreat w/ Detached Studio!
Distance to beach: 1 mi Oak Bluffs Town Beach and 0.9 mi to Eastville Beach
Summer:
 $3,000 - $5,000/wk
Off Season:
 $1,500 - $3,000/wk
7
Oak Bluffs
ID 9553
3 BR
2 baths
Sleeps 6
Oak Bluffs Family Vacation Home
Oak Bluffs Family Vacation Home
Distance to beach: Lagoon Eastville Beach and 3 miles State Beach (Joseph Sylvia State Beach)
3 reviews read reviews
Summer:
 $900 - $1,000/night
 $14,000 - $16,000/mo
Off Season:
 $700 - $800/night
 $1,500 - $2,800/wk
 $2,000 - $6,000/mo
10
Oak Bluffs
ID 9028
3 BR
2 ½ baths
Sleeps 6
Vineyard Retreat - The perfect place to rest and relax
Vineyard Retreat - The perfect place to rest and relax
Distance to beach: 2/10 mile to a beach on a large 3,968 acre pond
16 reviews read reviews
Summer:
 $3,600 - $4,500/wk
 $14,000 - $16,000/mo
Off Season:
 $3,000 - $3,700/wk
 $10,000 - $15,000/mo
4
Oak Bluffs
ID 12452
3 BR
1 ½ bath
Sleeps 6
Easy and comfortable Island home
Easy and comfortable Island home
Distance to beach: 1/4 mile Eastville Beach and 1/2 mile to Jette Beach
7 reviews read reviews
Summer:
 $3,400 - $4,000/wk
Off Season:
 $375/night
 $2,000 - $3,400/wk
5
Oak Bluffs
ID 32157
3 BR
2 baths
Sleeps 6
Charming Home On Farm Pond w/ Ocean View walk to Inkwell
Charming Home On Farm Pond w/ Ocean View walk to Inkwell
Distance to beach: 4/10 mile to Inkwell Beach
1 review read review
Summer:
 $3,750 - $4,675/wk
Off Season:
 $2,500 - $3,750/wk
2
Oak Bluffs - East Chop
ID 29421
3 BR
2 ½ baths
Sleeps 6
Ocean, Ferry & Sunset Views - Relax and Unwind
Ocean, Ferry & Sunset Views - Relax and Unwind
Distance to beach: 3/4 mile Oak Bluffs Town Beach, E Chop Beach Club
Summer:
 $7,000 - $8,500/wk
Off Season:
 $500 - $850/night
 $3,500 - $8,500/wk
 $7,000 - $14,000/mo
6
Oak Bluffs
ID 34172
3 BR
2 ½ baths
Sleeps 6
Vineyard Get-Away
Vineyard Get-Away
Distance to beach: 2.6 mi to Oak Bluffs Town Beach
12 reviews read reviews
Summer:
 $3,650 - $6,500/wk
Off Season:
 $3,500 - $4,000/wk
3
Oak Bluffs
ID 35638
3 BR
2 ½ baths
Sleeps 6
Modern Gingerbread Home, Walking Distance to Lagoon
Modern Gingerbread Home, Walking Distance to Lagoon
Distance to beach: 1.5 mi to Oak Bluffs Town Beach and 1.0 mi to Eastville Beach
5
Oak Bluffs
ID 36904
3 BR
2 baths
Sleeps 6
East Chop Tree Tops
East Chop Tree Tops
Distance to beach: 0.9 miles The Jetty Beach and 1.1 miles Eastville Beach
Off Season:
 $395 - $449/night
 $2,765 - $2,999/wk
Lagoon Heights
ID 36917
3 BR
2 baths
Sleeps 6
Cozy Cape near Lagoon
Cozy Cape near Lagoon
Distance to beach: 3 Blocks Walking distance to Lagoon
Summer:
 $4,500 - $5,000/wk
Off Season:
 $575 - $700/night
 $3,500 - $5,000/wk
3
Oak Bluffs
ID 37210
3 BR
1 bath
Sleeps 6
Birds of Paradise - Walk to Beaches and Town
Birds of Paradise - Walk to Beaches and Town
Distance to beach: 1/2 mi to Oak Bluffs Town Beach
Summer:
 $3,000 - $4,500/wk
Off Season:
 $2,500 - $4,500/wk
2
Oak Bluffs
ID 37557
3 BR
2 ½ baths
Sleeps 6
Pristine Home in Oak Bluffs/Close to Downtown
Pristine Home in Oak Bluffs/Close to Downtown
Distance to beach: 1 mi to Eastville Beach and 1.2 mi to Inkwell Beach
2 reviews read reviews
Off Season:
 $3,100 - $4,200/wk
Oak Bluffs
ID 37987
3 BR
2 baths
Sleeps 6
Renovated Cottage in Convenient Location to Beaches and Town
Renovated Cottage in Convenient Location to Beaches and Town
Distance to beach: 1.3 mi to Oak Bluffs Town Beach
1 review read review
Summer:
 $650 - $750/night
 $3,000 - $3,500/wk
Off Season:
 $300 - $400/night
 $2,500 - $4,000/wk
Oak Bluffs
ID 39483
3 BR
2 baths
Sleeps 6
Top Notch Vacation Rentals (Walk to Sengekontacket Pond)
Top Notch Vacation Rentals (Walk to Sengekontacket Pond)
Distance to beach: 1 mi to Oak Bluffs Town Beach and 5 min walk to Sengekontacket Pond
Summer:
 $5,000/wk
Off Season:
 $650 - $700/night
 $2,500 - $3,000/wk
Oak Bluffs
ID 33919
2 BR
2 ½ baths
Sleeps 6
Oak Bluffs Retreat - The perfect getaway!
Oak Bluffs Retreat - The perfect getaway!
Distance to beach: 1.3 mi to Oak Bluffs Town Beach
2 reviews read reviews
Summer:
 $3,325 - $4,655/wk
Off Season:
 $390 - $545/night
 $3,255 - $3,990/wk
Oak Bluffs
ID 38986
2 BR
2 ½ baths
Sleeps 6
Happy Place in OB
Happy Place in OB
Distance to beach: 0.8 mi to Oak Bluffs Town Beach
Summer:
 $6,500 - $7,000/wk
Off Season:
 $700 - $800/night
 $3,850 - $6,500/wk
5
Oak Bluffs
ID 27087
2 BR
1 bath
Sleeps 6
Oak Bluffs Getaway
Oak Bluffs Getaway
Distance to beach: Lagoon
In-Town of Oak Bluffs
ID 36162
2 BR
3 ½ baths
Sleeps 6
Charming Cottage in Great OB Location
Charming Cottage in Great OB Location
Distance to beach: 4/10 mi to Oak Bluffs Town Beach
Summer:
 $5,000 - $6,000/wk
Off Season:
 $500 - $1,000/night
 $5,000/wk
3

Oak Bluffs vacation rentals that sleep 5

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Oak Bluffs
ID 16588
3 BR
1 ½ bath
Sleeps 5
Vanessa's Hide-Away; ferry res. avail. 7/29-8/5
Vanessa's Hide-Away; ferry res. avail. 7/29-8/5
Distance to beach: 2 minute walk to Oak Bluffs Beaches
5 reviews read reviews
Summer:
 $3,595 - $4,695/wk
Off Season:
 $3,495 - $4,295/wk
Oak Bluffs
ID 21790
3 BR
1 ½ bath
Sleeps 5
Ideal location, short walk to Town & Beach, 3 night min Sept
Ideal location, short walk to Town & Beach, 3 night min Sept
Distance to beach: 7 min walk Oak Bluffs Town Beach and 7-minute walk to Inkwell Beach
10 reviews read reviews
Summer:
 $2,895 - $4,495/wk
Off Season:
 $480/night
 $2,695 - $3,695/wk
Oak Bluffs
ID 35306
3 BR
1 ½ bath
Sleeps 5
BEACH COTTAGE, SUNSETS, LAGOON, 3 BR, AC
BEACH COTTAGE, SUNSETS, LAGOON, 3 BR, AC
Distance to beach: 2.4 mi to Oak Bluffs Town Beach and your own Private Beach on Lagoon Pond
OWNER SPECIAL:
2025 Book Now ! weeks still available at this wonderful Beach house. Call asap.
Summer:
 $7,000 - $10,000/wk
Off Season:
 $6,000 - $6,500/wk
Oak Bluffs, near Inkwell Beach
ID 24640
3 BR
1 ½ bath
Sleeps 5
Jingle Shell Cottage, quiet locale, walk to beach & town!
Jingle Shell Cottage, quiet locale, walk to beach & town!
Distance to beach: 1200 feet Oak Bluffs Town Beach and 1000 feet to Inkwell Beach
2 reviews read reviews
Oak Bluffs
ID 10417
2 BR
1 bath
Sleeps 5
Cozy cottage about 700 ft from the Inkwell Beach
Cozy cottage about 700 ft from the Inkwell Beach
Distance to beach: Inkwell/Town Beach Oak Bluffs Town Beach and 700 ft to town beach
1 review read review
Summer:
 $3,000/wk
Off Season:
 $2,300/wk
2
Oak Bluffs
ID 36583
2 BR
2 baths
Sleeps 5
Cozy-Cottage-Glam off Circuit Great Outdoor Living.2Bd/2B
Cozy-Cottage-Glam off Circuit Great Outdoor Living.2Bd/2B
Distance to beach: 4/10 mi to Inkwell Oak Bluffs Town Beach
2 reviews read reviews
Summer:
 $6,000 - $7,000/wk
Off Season:
 $500/night
 $3,500 - $6,500/wk
Copeland Historic District
ID 35333
2 BR
1 bath
Sleeps 5
5 Minute Walk to Circuit Ave and Town Beach
5 Minute Walk to Circuit Ave and Town Beach
Distance to beach: 3/10 mi to Oak Bluffs Town Beach
3 reviews read reviews
Summer:
 $2,600/wk
Off Season:
 $2,600/wk
9

Oak Bluffs vacation rentals that sleep 4

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Oak Bluffs
ID 35127
2 BR
2 ½ baths
Sleeps 4
Charming Cottage Located in Heart of Oak Bluffs
Charming Cottage Located in Heart of Oak Bluffs
Distance to beach: 0.2 mi to Oak Bluffs Town Beach
Summer:
 $4,750 - $8,400/wk
Off Season:
 $2,900 - $5,040/wk
East Chop
ID 38085
2 BR
1 bath
Sleeps 4
Gorgeous Cabin with Gorgeous Views (Walk to beach and town)
Gorgeous Cabin with Gorgeous Views (Walk to beach and town)
Distance to beach: 0.5 mi to The Jetty Beach and 0.5 mi to Oak Bluffs Town Beach
3 reviews read reviews
Summer:
 $6,000 - $7,250/wk
Off Season:
 $500/night
 $2,500 - $7,250/wk
 $3,000/mo
7
Oak Bluffs
ID 38849
2 BR
1 bath
Sleeps 4
Oak Bluffs Cottage Walk to Town & Beach
Oak Bluffs Cottage Walk to Town & Beach
Distance to beach: .75 miles The Jetty Beach and 3/4 Mile to The Inkwell Beach
OWNER SPECIAL:
Price Reduced! Fall Beauty Awaits! 3 Night Escape without the Crowds!
Summer:
 $3,150 - $9,450/wk
Off Season:
 $450/night
 $2,800 - $3,850/wk
Oak Bluffs
ID 30504
2 BR
1 bath
Sleeps 4
OAK BLUFFS GETAWAY
OAK BLUFFS GETAWAY
Distance to beach: 9/10 mile to Inkwell Beach
6 reviews read reviews
Off Season:
 $3,000/wk
3
Oak Bluffs on the Edgartown li
ID 37184
2 BR
1 ½ bath
Sleeps 4
Quiet and Comfortable - Come and Stay a While!
Quiet and Comfortable - Come and Stay a While!
Distance to beach: 5.5 miles State Beach and 7 miles South Beach - Katama
1 review read review
Summer:
 $3,000 - $3,500/wk
 $10,000/mo
Off Season:
 $3,000/wk
 $10,000/mo
East Chop (Oak Bluffs)
ID 4096
1 BR
1 bath
Sleeps 4
Beautiful Cottage Retreat: Reminiscent of Summer Traditions
Beautiful Cottage Retreat: Reminiscent of Summer Traditions
Distance to beach: 2/10 mile to Oak Buffs Harbor/Marina Beach
3 reviews read reviews
Summer:
 $10,000/mo
Off Season:
 $9,000 - $10,000/mo
Oak Bluffs
ID 37211
1 BR
1 bath
Sleeps 4
Relax and Rejuvenate in a brand new cozy apartment!
Relax and Rejuvenate in a brand new cozy apartment!
Distance to beach: 2.8 mi to Oak Bluffs Town Beach and .4 mi to Sailing Camp Beach
Summer:
 $250 - $500/night
 $2,500 - $3,500/wk
 $11,000 - $13,000/mo
Off Season:
 $2,000 - $3,000/wk
 $2,000 - $10,000/mo
6

Oak Bluffs vacation rentals that sleep 3

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Oak Bluffs
ID 34370
2 BR
1 bath
Sleeps 3
Absolutely Amazing... Lovely, Cozy Garden Cottage
Absolutely Amazing... Lovely, Cozy Garden Cottage
Distance to beach: 9/10 mi to The Jetty Beach
Off Season:
 $975 - $1,050/night
4
Oak Bluffs
ID 34153
1 BR
1 bath
Sleeps 3
Perfect One Bedroom Garage Apartment w/AC
Perfect One Bedroom Garage Apartment w/AC
Distance to beach: 1.1 mi to The Jetty Beach and 1.3 to Inkwell Beach
7 reviews read reviews
Summer:
 $1,500 - $2,500/wk
Off Season:
 $1,500/wk
3
Oak Bluffs
ID 21977
1 BR
1 bath
Sleeps 3
Wooded Haven, Martha's Vineyard Oasis
Wooded Haven, Martha's Vineyard Oasis
Distance to beach: 1.5 miles to Oak Bluffs Town Beach and 5/10 mile to Eastville Beach
18 reviews read reviews
Summer:
 $2,800 - $3,000/wk
 $10,000 - $12,000/mo
Off Season:
 $1,500 - $2,600/wk
3
Oak Bluffs
ID 36402
1 BR
1 bath
Sleeps 3
Renovated Cozy Seaside Cottage with Views of Town Beach
Renovated Cozy Seaside Cottage with Views of Town Beach
Distance to beach: 200 feet to Oak Bluffs Town Beach
Off Season:
 $2,500 - $3,000/wk

Oak Bluffs vacation rentals that sleep 2

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Oak Bluffs
ID 32208
1 BR
1 bath
Sleeps 2
''The Nest'' Guest House: Steps to Beach/town, Water Views!
''The Nest'' Guest House: Steps to Beach/town, Water Views!
Distance to beach: 1/10 of a mile to Oak Bluffs Town Beach and a short bike ride on the path State Beach
8 reviews read reviews
OWNER SPECIAL:
Ask about flexible dates!
Summer:
 $350 - $600/night
 $2,900 - $4,700/wk
 $9,000 - $13,000/mo
Off Season:
 $325 - $500/night
 $2,200 - $2,900/wk
 $6,000 - $11,800/mo
2
Oak Bluffs
ID 39272
1 BR
1 bath
Sleeps 2
East Chop Waterfront
East Chop Waterfront
Distance to beach: Beachfront private beach
Summer:
 $3,500 - $4,500/wk
Off Season:
 $3,000 - $4,000/wk
Oak Bluffs
ID 11609
1 BR
1 bath
Sleeps 2
Sweet Pea Cottage, Walk To Beach
Sweet Pea Cottage, Walk To Beach
Distance to beach: 1/10 mile Oak Bluffs Town Beach
69 reviews read reviews
Off Season:
 $385/night
 $1,850 - $2,650/wk
Oak Bluffs
ID 13623
1 BR
1 bath
Sleeps 2
Best Direct Waterfront Value, Incredible Location
Best Direct Waterfront Value, Incredible Location
Distance to beach: 2/10 mile to East Chop Jetty beach
Summer:
 $3,695/wk
Off Season:
 $2,995 - $3,695/wk
4