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Mid Cape Cod Vacation Rentals

Osterville Vacation Rentals

Osterville is an exclusive seaside community on Nantucket Sound. Elegant waterfront homes, many of which were built in the 19th century, line the main streets.

22 Vacation Properties in Osterville
Sleeps

Osterville vacation rentals that sleep 14

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Osterville
ID 37315
7 BR
5 ½ baths
Sleeps 14
Impressive Osterville Residence - w/Guest House
Impressive Osterville Residence - w/Guest House
Distance to beach:

Osterville vacation rentals that sleep 12

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Osterville
ID 36579
5 BR
4 ½ baths
Sleeps 12
Wianno Ave Home With Pool
Wianno Ave Home With Pool
Distance to beach: 0.6 mi to Dowses and Sea View Beach
Off Season:
 $25,000/wk

Osterville vacation rentals that sleep 10

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Osterville/ Centerville Line
ID 39006
5 BR
3 baths
Sleeps 10
* New 2024* Luxury Coastal Retreat w/ Heated Saltwater Pool
* New 2024* Luxury Coastal Retreat w/ Heated Saltwater Pool
Distance to beach: 1.4 mi to Joshua Pond and 2.4 mi Dowses
Off Season:
 $1,072 - $1,500/night
 $5,000 - $8,500/wk
2
Osterville
ID 35972
4 BR
2 ½ baths
Sleeps 10
One summer week left!!! 8/23-Osterville retreat
One summer week left!!! 8/23-Osterville retreat
Distance to beach: 2.4 mi to Dowses
9 reviews read reviews
Summer:
 $3,950/wk
Off Season:
 $350 - $450/night
 $3,000 - $3,950/wk
 $3,000 - $4,000/mo
2
Osterville
ID 37082
4 BR
3 ½ baths
Sleeps 10
Seasons by the Sea-newly renovated home sleeps up to 10
Seasons by the Sea-newly renovated home sleeps up to 10
Distance to beach: 1/2 mi to Joshua Pond and 2 mi to Dowses
4 reviews read reviews
OWNER SPECIAL:
Reduced minimum stay in off Season with new nightly rate. Inquire for more info.
Summer:
 $8,750/wk
Off Season:
 $750 - $1,000/night
 $5,250 - $8,750/wk
4
Osterville
ID 37549
4 BR
2 baths
Sleeps 10
Spacious Home, Quiet Neighborhood, Great for Families
Spacious Home, Quiet Neighborhood, Great for Families
Distance to beach: .8 miles Joshua Pond and 2.1 mi to Dowses
12 reviews read reviews
Off Season:
 $400 - $500/night
 $2,800 - $3,500/wk
5
Osterville
ID 37314
4 BR
4 ½ baths
Sleeps 10
Sea View Ave - New Construction - Pool Hot Tub Tennis Court
Sea View Ave - New Construction - Pool Hot Tub Tennis Court
Distance to beach: 0.25 mi to Dowses
Off Season:
 $35,000/wk

Osterville vacation rentals that sleep 9

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Osterville
ID 38500
4 BR
3 ½ baths
Sleeps 9
Walking Distance to French Bakery/Beach Pass Provided
Walking Distance to French Bakery/Beach Pass Provided
Distance to beach: 2.9 mi to Dowses Beach; 4.9 mi to Craigville Beach
Off Season:
 $400 - $600/night
 $2,000 - $4,400/wk
 $3,800 - $4,000/mo
3
Osterville
ID 35895
3 BR
2 ½ baths
Sleeps 9
Osterville- New renovation, central AC, beach pass included
Osterville- New renovation, central AC, beach pass included
Distance to beach: 3/10 mi to Joshua Pond
13 reviews read reviews
Summer:
 $4,370 - $4,515/wk
Off Season:
 $275 - $350/night
 $550 - $2,525/wk
3
Osterville - Barnstable
ID 36837
3 BR
2 baths
Sleeps 9
Labor Day Special with Beach Pass
Labor Day Special with Beach Pass
Distance to beach: 1/2 mile Joshua Pond and 2 miles Dowses
5 reviews read reviews
Summer:
 $2,500 - $3,300/wk
 $10,000 - $13,000/mo
Off Season:
 $400 - $450/night
 $1,500 - $2,500/wk
 $4,000 - $8,000/mo
2

Osterville vacation rentals that sleep 8

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Osterville
ID 37412
3 BR
2 baths
Sleeps 8
Pristine Family Vacation Home/Beach Pass Included
Pristine Family Vacation Home/Beach Pass Included
Distance to beach: 1.8 mi to Joshua Pond and 3.2 Dowses
6 reviews read reviews
Summer:
 $2,400 - $3,200/wk
Off Season:
 $315 - $370/night
 $2,200 - $2,400/wk
Osterville
ID 34432
3 BR
2 baths
Sleeps 8
Updated 3 Bedroom with AC & Great Proximity to Summer Fun
Updated 3 Bedroom with AC & Great Proximity to Summer Fun
Distance to beach: 1.2 mi to Dowses and 3.5 mi Craigville Beach
4 reviews read reviews
Off Season:
 $2,500/wk
3
Osterville
ID 37316
3 BR
1 ½ bath
Sleeps 8
Osterville Village - Large Yard & Outdoor Patio
Osterville Village - Large Yard & Outdoor Patio
Distance to beach: 1 mile to Dowses

Osterville vacation rentals that sleep 7

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Osterville
ID 23526
3 BR
2 baths
Sleeps 7
Delightful Osterville Haven. Walk to Main St. and a Swim!
Delightful Osterville Haven. Walk to Main St. and a Swim!
Distance to beach: 3/10 mile to Joshua Pond and 1 mile to Dowses
34 reviews read reviews
Summer:
 $3,077 - $3,355/wk
Off Season:
 $1,780 - $2,696/wk
4
Osterville Barnstable
ID 19650
3 BR
2 baths
Sleeps 7
Spacious Family Getaway Home
Spacious Family Getaway Home
Distance to beach: 2 1/2 Craigville Beach and 2 miles Dowses Beach
13 reviews read reviews
Summer:
 $2,300/wk
 $10,600/mo
Off Season:
 $295 - $325/night
 $2,000 - $2,200/wk
7

Osterville vacation rentals that sleep 6

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Osterville Woods
ID 35272
3 BR
3 baths
Sleeps 6
Osterville Great Family Rental!
Osterville Great Family Rental!
Distance to beach: 1.5 Joshua Pond and 3.0 Dowses
Summer:
 $2,600 - $3,200/wk
Off Season:
 $225 - $230/night
 $2,000 - $2,850/wk
 $2,500 - $3,000/mo
6
Osterville
ID 38319
3 BR
2 baths
Sleeps 6
Dog Friendly Charmer - Convenient Location
Dog Friendly Charmer - Convenient Location
Distance to beach: 1.6 miles Joshua Pond and 3.0 miles Dowses
Summer:
 $1,800/wk
Off Season:
 $175 - $215/night
 $1,500 - $1,800/wk
 $2,000/mo
5
Osterville
ID 38786
3 BR
2 baths
Sleeps 6
Newly Renovated Osterville Home: Beach Pass Included
Newly Renovated Osterville Home: Beach Pass Included
Distance to beach: 1.6 mi to Joshua Pond and 1.5 mi Dowses
2 reviews read reviews
OWNER SPECIAL:
Price Reduction and 2025 Summer Special.
Summer:
 $3,200/wk
Off Season:
 $350 - $650/night
 $2,500 - $3,000/wk
2
Osterville
ID 36955
3 BR
2 baths
Sleeps 6
Spacious Home/Walk to Town/Beach Pass & Kayaks Included
Spacious Home/Walk to Town/Beach Pass & Kayaks Included
Distance to beach: 1.0 mi to Dowses and 1.0 mi to Craigville Beach
Off Season:
 $4,000 - $5,000/wk
2
Carriage House
ID 38342
3 BR
2 baths
Sleeps 6
Carriage House - Oceanfront - Overlooking Dowses Beach
Carriage House - Oceanfront - Overlooking Dowses Beach
Distance to beach: 5/10 to dowses Dowses and private beach off wooden walkway on the property
Off Season:
 $7,500/wk

Osterville vacation rentals that sleep 4

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Osterville
ID 34848
2 BR
1 ½ bath
Sleeps 4
Enchanting Cottage - one block to Osterville Village!
Enchanting Cottage - one block to Osterville Village!
Distance to beach: 0.5 mi to Joshua Pond and 1.5 mi to Dowses
7 reviews read reviews
Off Season:
 $1,500 - $2,000/wk
 $2,500 - $6,000/mo

Osterville vacation rentals that sleep 3

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Osterville
ID 37628
3 BR
3 ½ baths
Sleeps 3
Charming Osterville Home w/ Pool - Near Town
Charming Osterville Home w/ Pool - Near Town
Distance to beach: 600 ft to Joshua Pond and 1.5 mi to Dowses
Off Season:
 $800 - $850/night
 $6,000 - $9,000/wk