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Martha's Vineyard Vacation Rentals

Vineyard Haven Vacation Rentals

Originally a fishing village and a bustling seaport during the whaling era, the Vineyard Haven of today is home to charming shops, popular restaurants and a beautiful harbor, often filled with private yachts.

58 Vacation Properties in Vineyard Haven
Sleeps

Vineyard Haven vacation rentals that sleep 18

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Vineyard Haven
ID 37866
9 BR
6 ½ baths
Sleeps 18
Historic Captain's House/Sleeps 18/Walk to Ferry & Beaches
Historic Captain's House/Sleeps 18/Walk to Ferry & Beaches
Distance to beach: 1/2 mi to Eastville Beach and across the street from Owen Park Beach
2 reviews read reviews
Summer:
 $14,000 - $26,000/wk
Off Season:
 $2,500 - $3,000/night
 $8,000 - $18,000/wk
4

Vineyard Haven vacation rentals that sleep 14

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Vineyard Haven
ID 34385
7 BR
4 baths
Sleeps 14
Magnificent 7 Bedroom, West Chop, Beachfront, Dock & Tennis!
Magnificent 7 Bedroom, West Chop, Beachfront, Dock & Tennis!
Distance to beach: Gorgeous Shared Private Beach
Summer:
 $1,500 - $2,500/night
 $10,250 - $12,250/wk
Off Season:
 $900 - $1,500/night
 $5,000 - $9,000/wk
4

Vineyard Haven vacation rentals that sleep 13

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West Chop Waterfront
ID 38244
6 BR
3 baths
Sleeps 13
West Chop Waterfront Home with Private Beach
West Chop Waterfront Home with Private Beach
Distance to beach: Private sandy beach
Summer:
 $10,000 - $20,000/wk
Off Season:
 $5,000 - $15,000/wk

Vineyard Haven vacation rentals that sleep 12

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Vineyard Haven
ID 35726
6 BR
6 ½ baths
Sleeps 12
Private Estate with Pool and Tennis
Private Estate with Pool and Tennis
Distance to beach: 2.4 mi to Lake Tashmoo Town Beach
Summer:
 $15,000 - $28,000/wk
Off Season:
 $15,000 - $22,000/wk
Vineyard Haven
ID 39172
6 BR
4 ½ baths
Sleeps 12
Luxurious Six-Bedroom Vineyard Haven Cottage/Walk to Beach
Luxurious Six-Bedroom Vineyard Haven Cottage/Walk to Beach
Distance to beach: 1/10 mile to Tisbury Town Beach
1 review read review
Summer:
 $12,000 - $14,000/wk
Off Season:
 $500 - $800/night
 $5,000 - $12,000/wk
10
Vineyard Haven
ID 38942
5 BR
6 ½ baths
Sleeps 12
Luxurious Beachfront Haven w/ Private Dock & Views
Luxurious Beachfront Haven w/ Private Dock & Views
Distance to beach: Situated on Private Beach
Summer:
 $15,000 - $35,000/wk
Off Season:
 $1,700 - $2,100/night
 $9,000 - $25,000/wk
4
Vineyard Haven
ID 27594
5 BR
2 ½ baths
Sleeps 12
Main House near Lagoon & Town
Main House near Lagoon & Town
Distance to beach: 4 miles State Beach and Less than one mile to Lagoon Beach via wooded hike
Off Season:
 $500 - $900/night
 $4,500 - $6,000/wk
5

Vineyard Haven vacation rentals that sleep 10

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Waterfront in Vineyard Haven
ID 38336
6 BR
4 ½ baths
Sleeps 10
Vineyard Haven Waterfront with Mooring
Vineyard Haven Waterfront with Mooring
Distance to beach: 0.2 mi to Eastville Beach and water access from the house
Summer:
 $20,000 - $22,000/wk
Vineyard Haven
ID 16690
5 BR
2 ½ baths
Sleeps 10
Vineyard Haven (in town), Recently Renovated, Harbor views
Vineyard Haven (in town), Recently Renovated, Harbor views
Distance to beach: 1 block to Owen Park Beach
11 reviews read reviews
Summer:
 $6,900 - $7,400/wk
Off Season:
 $6,900/wk
3
VINEYARD HAVEN
ID 35577
5 BR
4 ½ baths
Sleeps 10
Reunion House: Car + Ferry Tickets
Reunion House: Car + Ferry Tickets
Distance to beach: 1.5 miles to James Pond Preserve (Lambert's Cove)
8 reviews read reviews
Summer:
 $7,725 - $10,750/wk
Off Season:
 $4,000 - $8,000/wk
9
Vineyard Haven
ID 39248
5 BR
3 ½ baths
Sleeps 10
Luxury Getaway With Pool and Private Association Beach
Luxury Getaway With Pool and Private Association Beach
Distance to beach: 1.2 mi to Eastville Beach and Mink Meadows Association Beach
Summer:
 $15,000 - $18,900/wk
Off Season:
 $1,000 - $1,785/night
 $6,750 - $13,500/wk
West Chop Water Front
ID 38856
5 BR
4 ½ baths
Sleeps 10
West Chop Waterfront
West Chop Waterfront
Distance to beach: Water Front path to Association Beach
2
Vineyard Haven
ID 30546
4 BR
3 baths
Sleeps 10
4-Bedroom Vineyard Haven Home
4-Bedroom Vineyard Haven Home
Distance to beach: 1.2 miles to Owen Park Beach
18 reviews read reviews
Summer:
 $4,500 - $6,500/wk
Off Season:
 $400 - $500/night
 $3,000 - $5,500/wk
3
Lower Makonikey, off Lambert's
ID 3695
4 BR
3 baths
Sleeps 10
Secluded 4+br home: short walk to private association beach
Secluded 4+br home: short walk to private association beach
Distance to beach: 4/10 mile to private Lower Makonikey Beach
19 reviews read reviews
Summer:
 $4,500 - $4,600/wk
5
Off Main Street
ID 33483
4 BR
2 baths
Sleeps 10
Great Wedding Season Rental Walk to town & Beach. Family Fun
Great Wedding Season Rental Walk to town & Beach. Family Fun
Distance to beach: 2/10 mi to Tisbury Town Beach
5 reviews read reviews
Summer:
 $6,000 - $7,500/wk
Off Season:
 $4,000 - $6,000/wk
2

Vineyard Haven vacation rentals that sleep 9

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Vineyard Haven
ID 18566
4 BR
2 baths
Sleeps 9
Waterfront Cottage with Private Beach
Waterfront Cottage with Private Beach
Distance to beach: On the beach
6 reviews read reviews
Summer:
 $5,000 - $6,900/wk
Off Season:
 $2,750 - $4,400/wk
Vineyard Haven
ID 29874
4 BR
4 baths
Sleeps 9
Luxury 4 Ensuite Bedrooms, Pool, Spa, Cabana Walk To Town VH
Luxury 4 Ensuite Bedrooms, Pool, Spa, Cabana Walk To Town VH
Distance to beach: .5 miles Owen Park Beach and Owen Park Beach 1/2 mile
Summer:
 $16,000 - $20,000/wk
Off Season:
 $1,000 - $1,800/night
 $7,000 - $12,000/wk
2
VIneyard Haven
ID 37130
4 BR
2 ½ baths
Sleeps 9
Updated Vineyard Farmhouse - Walk to Town & Ferry
Updated Vineyard Farmhouse - Walk to Town & Ferry
Distance to beach: 1.0 mi to Tisbury Town Beach and 0.7 mi to Owen Park Beach
Off Season:
 $350 - $550/night
 $3,360 - $4,130/wk

Vineyard Haven vacation rentals that sleep 8

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Vineyard Haven
ID 28634
4 BR
2 baths
Sleeps 8
Secluded In-Town Wonder: The Best Of Both Worlds
Secluded In-Town Wonder: The Best Of Both Worlds
Distance to beach: 1/2 mile to Owen Park Beach and 1/4 mile to Owen Park Beach.
Summer:
 $3,900 - $4,950/wk
Off Season:
 $3,700/wk
5
Vineyard Haven
ID 34561
4 BR
2 baths
Sleeps 8
A/C Home w/ Peaceful Pool
A/C Home w/ Peaceful Pool
Distance to beach: 10 minute walk to Owen's Beach State Park
2 reviews read reviews
Summer:
 $6,000 - $10,000/wk
Off Season:
 $5,000 - $7,000/wk
Vineyard Haven
ID 36965
4 BR
2 baths
Sleeps 8
Charming, Centrally Located Vineyard Home
Charming, Centrally Located Vineyard Home
Distance to beach: 1 mile Owen Park Beach and 4 miles Oak Bluffs Town Beach
10 reviews read reviews
Summer:
 $3,500 - $6,000/wk
Off Season:
 $2,000 - $3,500/wk
 $3,500 - $4,000/mo
Vineyard Haven (West Chop)
ID 37892
4 BR
2 baths
Sleeps 8
Newly Renovated West Chop/Walk to Beach, Golf, and Ferry
Newly Renovated West Chop/Walk to Beach, Golf, and Ferry
Distance to beach: 1/2 mi to Tisbury Town Beach and 4 mi to Lake Tashmoo Town Beach
7 reviews read reviews
OWNER SPECIAL:
Early Booking Special… Book 2 weeks or more and save 10%!
Summer:
 $4,500 - $6,500/wk
Off Season:
 $1,500 - $4,500/wk
4
Vineyard Haven
ID 38171
4 BR
3 baths
Sleeps 8
Main Street Charmer
Main Street Charmer
Distance to beach: 0.2 mi to Tisbury Town Beach
Summer:
 $2,800 - $4,750/wk
Off Season:
 $2,500 - $4,750/wk
Vineyard Haven
ID 39177
4 BR
3 baths
Sleeps 8
Private Beachfront Cottage that Has It All
Private Beachfront Cottage that Has It All
Distance to beach: 0.5 mi to Owen Park Beach and Private beach right in front of the home.
Summer:
 $6,000/wk
Off Season:
 $250 - $500/night
 $5,000/wk
3
VIneyard Haven
ID 39682
4 BR
2 ½ baths
Sleeps 8
The Bellevue - Stunning 4/2.5 Water View, Hot Tub
The Bellevue - Stunning 4/2.5 Water View, Hot Tub
Distance to beach: 1.0 mi to Tisbury Town Beach and Under 3 miles to Inkwell Beach, Oak Bluffs
15 reviews read reviews
Summer:
 $6,900 - $8,400/wk
Off Season:
 $399 - $950/night
 $3,500 - $6,900/wk
 $7,000 - $8,000/mo
6
Martha's Vineyard
ID 28424
4 BR
4 ½ baths
Sleeps 8
Captain Spring House: In-town Luxury with Water Views
Captain Spring House: In-town Luxury with Water Views
Distance to beach: 3/10 mile Owen Park Bch, 1/2 mile Town Beach
1 review read review
Off Season:
 $750 - $1,000/night
 $5,250 - $7,990/wk
4
Vineyard Haven
ID 3110
3 BR
2 baths
Sleeps 8
Peaceful Escape | Charming Vacation Home w/ AC
Peaceful Escape | Charming Vacation Home w/ AC
Distance to beach: 1.0 mile Owen Park Beach and 1.5 miles Lake Tashmoo Town Beach
16 reviews read reviews
OWNER SPECIAL:
"Fall" In Love w/ MV - Special $400 per night rate w/ cleaning included 10/1-12/25 (3 night minimum)
Summer:
 $4,200/wk
Off Season:
 $450 - $500/night
 $2,200 - $3,400/wk
3
Vineyard Haven
ID 36073
3 BR
3 baths
Sleeps 8
West Chop/Private Setting...Two Private Beaches
West Chop/Private Setting...Two Private Beaches
Distance to beach: 1/4 mile to Private Association Beach
6 reviews read reviews
Summer:
 $6,825/wk
Off Season:
 $4,200 - $6,650/wk
4

Vineyard Haven vacation rentals that sleep 7

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Vineyard Haven
ID 29593
4 BR
2 ½ baths
Sleeps 7
Remaining Weeks Discounted! A/C, Walk to Town/Beach/Ferry
Remaining Weeks Discounted! A/C, Walk to Town/Beach/Ferry
Distance to beach: 2/10 mile Tisbury Town Beach and 3/10 Owen Park Beach
12 reviews read reviews
Off Season:
 $2,500 - $3,500/wk
5
Downtown Vineyard Haven
ID 29406
3 BR
3 ½ baths
Sleeps 7
MV Modern Farmhouse
MV Modern Farmhouse
Distance to beach: A few blocks to Owen Park Beach
2 reviews read reviews
Summer:
 $6,000 - $13,500/wk
Off Season:
 $4,500 - $10,000/wk
5

Vineyard Haven vacation rentals that sleep 6

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Vineyard Haven
ID 11693
3 BR
2 baths
Sleeps 6
Charming Cottage near West Chop- Vineyard Haven
Charming Cottage near West Chop- Vineyard Haven
Distance to beach: 2 Blks to Owen Little Beach-1 mi. to Tashmoo Beach
5 reviews read reviews
Summer:
 $3,250 - $3,465/wk
Off Season:
 $2,500 - $3,465/wk
 $2,600 - $3,000/mo
Vineyard Haven
ID 29492
3 BR
2 baths
Sleeps 6
Amazing Views Year-Round, Private Beach, Great for Kayaking
Amazing Views Year-Round, Private Beach, Great for Kayaking
Distance to beach: Private beach on the property, 3/10 mile to public
22 reviews read reviews
Summer:
 $4,150 - $6,100/wk
Off Season:
 $329 - $659/night
 $2,250 - $4,700/wk
5
Vineyard Haven
ID 33283
3 BR
1 ½ bath
Sleeps 6
Commanding Lagoon Waterfront, Private Beach: 180° View
Commanding Lagoon Waterfront, Private Beach: 180° View
Distance to beach: 20 ft from the your own 250' private Lagoon Beach!
11 reviews read reviews
Summer:
 $7,750 - $12,500/wk
Off Season:
 $950 - $1,000/night
 $5,000 - $8,500/wk
7
Vineyard Haven
ID 27296
3 BR
1 ½ bath
Sleeps 6
Charming 3 Bedroom Home Close to Downtown & Lake Tashmoo!
Charming 3 Bedroom Home Close to Downtown & Lake Tashmoo!
Distance to beach: Lake Tashmoo, Owen Park, Wilfred's Pond
Summer:
 $2,600 - $2,900/wk
Off Season:
 $2,600/wk
3
Tisbury
ID 36737
3 BR
2 ½ baths
Sleeps 6
Walk to Town Beach, Downtown, Sunny Stylish VH Ranch
Walk to Town Beach, Downtown, Sunny Stylish VH Ranch
Distance to beach: one block Tisbury Town Beach
Summer:
 $5,400 - $6,000/wk
 $26,000 - $29,000/mo
Off Season:
 $5,400 - $5,900/wk
 $20,000 - $22,000/mo
6
Vineyard Haven
ID 37747
3 BR
2 baths
Sleeps 6
Waterfront Classic w/ Private Beach.Kayaks & Paddle Boards
Waterfront Classic w/ Private Beach.Kayaks & Paddle Boards
Distance to beach: Private BEACH on Lagoon Pond is 100 steps
2 reviews read reviews
Summer:
 $9,800/wk
8
Vineyard Haven
ID 37838
3 BR
2 baths
Sleeps 6
Wedding guest romantic weekend girls trip golf fishing
Wedding guest romantic weekend girls trip golf fishing
Distance to beach: 8/10 mile to Tisbury Town Beach and 2.2 Lake Tashmoo Town Beach
4 reviews read reviews
Summer:
 $3,800 - $5,800/wk
Off Season:
 $3,500 - $3,800/wk
4
Vineyard Haven
ID 37831
3 BR
3 baths
Sleeps 6
Vineyard Haven Townhouse with Pool
Vineyard Haven Townhouse with Pool
Distance to beach: 1.0 mi to Fuller Street Beach
Summer:
 $3,000 - $3,600/wk
Off Season:
 $343/night
 $2,400 - $3,000/wk
Vineyard Haven
ID 39147
3 BR
2 baths
Sleeps 6
Renovated Home Near Town Vineyard Haven
Renovated Home Near Town Vineyard Haven
Distance to beach: 2.1 mi to Tisbury Town Beach
OWNER SPECIAL:
Now Booking for 2025!!
Summer:
 $4,500 - $6,000/wk
Off Season:
 $500 - $1,000/night
 $4,000 - $4,500/wk
Vineyard Haven
ID 39287
3 BR
2 baths
Sleeps 6
Carefully Restored Captains House
Carefully Restored Captains House
Distance to beach: 0.8 mi to Tisbury Town Beach
Summer:
 $4,000 - $6,000/wk
Off Season:
 $3,000 - $6,000/wk
Vineyard Haven
ID 39473
3 BR
2 baths
Sleeps 6
Renovated Vineyard Retreat: Modern & Convenient Location
Renovated Vineyard Retreat: Modern & Convenient Location
Distance to beach: 1.7 mi to Tisbury Town Beach
Summer:
 $4,000 - $5,000/wk
 $18,000/mo
Off Season:
 $350 - $569/night
 $2,000 - $4,000/wk
 $7,000 - $15,000/mo
Vineyard Haven
ID 16365
2 BR
3 baths
Sleeps 6
Tashmoo Wood Condo
Tashmoo Wood Condo
Distance to beach: 1.5 mi to Lake Tashmoo Town Beach (Herring Creek)
Summer:
 $2,500 - $3,400/wk
Off Season:
 $2,000 - $3,400/wk
3
Vineyard Haven
ID 4482
2 BR
1 bath
Sleeps 6
Hine's Point Waterfront
Hine's Point Waterfront
Distance to beach: 1/2 mile
1 review read review
Off Season:
 $3,200 - $4,000/wk

Vineyard Haven vacation rentals that sleep 5

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Vineyard Haven
ID 7366
3 BR
1 ½ bath
Sleeps 5
Charming Lagoon Pond Cottage with Water View & Private Beach
Charming Lagoon Pond Cottage with Water View & Private Beach
Distance to beach: Private beach on property
17 reviews read reviews
Summer:
 $3,350/wk
Off Season:
 $2,512 - $3,350/wk
2
Vineyard Haven
ID 29565
2 BR
2 baths
Sleeps 5
Vineyard Charmer
Vineyard Charmer
Distance to beach: 1 mile Owen Park Beach
Summer:
 $3,250 - $3,600/wk
Off Season:
 $3,050 - $3,450/wk
2

Vineyard Haven vacation rentals that sleep 4

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Vineyard Haven
ID 19399
3 BR
2 baths
Sleeps 4
Charming Bright Sunny Cape Home in Vineyard Haven
Charming Bright Sunny Cape Home in Vineyard Haven
Distance to beach: 10 min walk Owen Park Beach and Lake Tashmoo Beach, Tisbury Town Beach also close
10 reviews read reviews
Summer:
 $2,400 - $2,700/wk
Off Season:
 $2,000 - $2,500/wk
 $2,000 - $2,200/mo
3
Vineyard Haven
ID 7436
2 BR
1 bath
Sleeps 4
Relax..You're on Island Time...A little piece of paradise..
Relax..You're on Island Time...A little piece of paradise..
Distance to beach: 1 mile Tisbury Town Beach and 1 mile Owen Park Beach
47 reviews read reviews
Summer:
 $1,800 - $2,000/wk
Off Season:
 $250 - $350/night
 $1,600 - $1,800/wk
 $1,700/mo
Vineyard Haven
ID 16502
2 BR
1 bath
Sleeps 4
Fabulous Contemporary With Steinway Piano & Tremendous Charm
Fabulous Contemporary With Steinway Piano & Tremendous Charm
Distance to beach: 3/4 Mile Owen Park Beach and Owen Park Beach, Appx. 3/4 mile from house.
Summer:
 $2,700 - $4,500/wk
Off Season:
 $500 - $750/night
 $1,600 - $3,500/wk
 $2,500 - $3,000/mo
6
Vineyard Haven
ID 34386
2 BR
2 baths
Sleeps 4
Architect Designed Two Bedroom Refuge w/Shared Private Beach
Architect Designed Two Bedroom Refuge w/Shared Private Beach
Distance to beach: Wonderful shared private beach just 200 feet away!
OWNER SPECIAL:
Tax Exempt When Renting 32+ Nights!
Summer:
 $4,000 - $5,500/wk
Off Season:
 $425 - $650/night
 $2,500 - $3,750/wk
 $2,600 - $13,000/mo
4
West Chop
ID 35609
2 BR
1 bath
Sleeps 4
Cozy West Chop Hideaway
Cozy West Chop Hideaway
Distance to beach: 0.9 mi to Tisbury Town Beach
2 reviews read reviews
Summer:
 $2,600 - $3,800/wk
Off Season:
 $1,500 - $2,900/wk
5
VIneyard Haven
ID 36738
2 BR
1 bath
Sleeps 4
Charming Vineyard Haven Cottage ~ Walk to Beach, Town, Park
Charming Vineyard Haven Cottage ~ Walk to Beach, Town, Park
Distance to beach: 4/10 mi Tisbury Town Beach
Summer:
 $4,900 - $5,900/wk
 $20,000 - $23,600/mo
Off Season:
 $3,000 - $4,900/wk
 $2,500 - $13,900/mo
6
Tisbury
ID 38371
2 BR
1 bath
Sleeps 4
Peaceful Upgraded Condo Minutes from VH and Ferry/Pool
Peaceful Upgraded Condo Minutes from VH and Ferry/Pool
Distance to beach: 0.8 miles Owen Park Beach
3 reviews read reviews
Off Season:
 $2,000/wk
3
Vineyard Haven
ID 39641
2 BR
1 bath
Sleeps 4
Waterfront Beach House! Incredible Sunsets and Lake access.
Waterfront Beach House! Incredible Sunsets and Lake access.
Distance to beach: 0.1 mi to Lake Tashmoo Town Beach and Sandy Path from House Leads to Private Beach
Summer:
 $5,500 - $6,750/wk
Off Season:
 $3,850 - $5,750/wk
1
Vineyard Haven
ID 31287
2 BR
1 bath
Sleeps 4
Lovely Vineyard Condo - Walk To Ferry - Flexible Dates
Lovely Vineyard Condo - Walk To Ferry - Flexible Dates
Distance to beach: 7/10 mile to Owen Park Beach
3 reviews read reviews
Summer:
 $2,200/wk
Off Season:
 $1,200 - $2,200/wk
2
Vineyard Haven
ID 38039
2 BR
2 baths
Sleeps 4
Cozy West Chop Cottage, Walk or Bike to Beach & Woods, Town
Cozy West Chop Cottage, Walk or Bike to Beach & Woods, Town
Distance to beach: 4/10 Mi to Grove Avenue Beach;1 mi Owen Park Beach
1 review read review
Summer:
 $450 - $650/night
 $3,999 - $4,999/wk
 $17,000 - $19,000/mo
Off Season:
 $299 - $699/night
 $2,100 - $4,999/wk
 $7,000 - $14,000/mo
5

Vineyard Haven vacation rentals that sleep 2

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Vineyard Haven
ID 21680
1 BR
1 bath
Sleeps 2
CCC - Cute, Cozy Condo with Pool
CCC - Cute, Cozy Condo with Pool
Distance to beach: Owen Park Beach under 1/2 mile
5 reviews read reviews
Summer:
 $1,000 - $1,125/wk
Off Season:
 $1,000 - $1,125/wk
Vineyard Haven
ID 29576
1 BR
1 bath
Sleeps 2
Stand Alone Condo Walking distance to Town and Ferry
Stand Alone Condo Walking distance to Town and Ferry
Distance to beach: 1 mile to Owen Park
Summer:
 $2,800 - $3,000/wk
Off Season:
 $300/wk
Vineyard Haven
ID 7718
1 BR
1 bath
Sleeps 2
Waterview of Vineyard Sound, sleeps 2.
Waterview of Vineyard Sound, sleeps 2.
Distance to beach: 10 minute walk to Owen Little Way Beach.
3 reviews read reviews
Off Season:
 $600 - $1,400/wk