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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.

30 Vacation Properties in Osterville
Sleeps

Osterville vacation rentals that sleep 14

Osterville
ID 37315
Summer:
$17,000/wk
Off Season:
$9,500 - $17,000/wk

Osterville vacation rentals that sleep 12

Osterville
ID 38649
Summer:
$26,297/wk
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
Summer:
$27,000/wk
Off Season:
$18,000 - $27,000/wk

Osterville vacation rentals that sleep 10

Osterville
ID 33824
Summer:
$4,500/wk
Off Season:
$4,500/wk
Osterville
ID 35972
Summer:
$4,950/wk
Off Season:
$350 - $450/night
$3,000 - $4,950/wk
$3,000 - $4,000/mo
2
Osterville
ID 37082
4 BR
3 ½ baths
Sleeps 10
Newly renovated home all ready for Christmas
Newly renovated home all ready for Christmas
Distance to beach: 1/2 mi to Joshua Pond and 2 mi to Dowses
4 reviews read reviews
OWNER SPECIAL:
Seasons by the Sea is ready for all the Seasons!
Summer:
$7,500/wk
Off Season:
$7,500/wk
4
Osterville
ID 37723
Summer:
$700 - $850/night
$5,075 - $6,099/wk
Off Season:
$700 - $850/night
$5,075/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
Summer:
$3,000/wk
Off Season:
$200 - $450/night
$2,000 - $3,000/wk
$3,500 - $5,000/mo
6
Osterville
ID 38533
Summer:
$6,500/wk
Off Season:
$929/night
$6,500/wk
Osterville
ID 37314
Summer:
$35,000/wk
Off Season:
$22,000 - $35,000/wk

Osterville vacation rentals that sleep 9

Osterville - Barnstable
ID 36837
3 BR
2 baths
Sleeps 9
Cape Escape - Minutes to Beaches w Barnstable Beach Pass
Cape Escape - Minutes to Beaches w Barnstable Beach Pass
Distance to beach: 1/2 mile Joshua Pond and 2 miles Dowses
4 reviews read reviews
Summer:
$2,500 - $3,200/wk
$12,000 - $14,000/mo
Off Season:
$300 - $350/night
$1,500 - $2,500/wk
$5,000 - $9,000/mo
2

Osterville vacation rentals that sleep 8

Osterville
ID 38313
Summer:
$8,000/wk
Off Season:
$7,500 - $8,000/wk
Osterville
ID 27473
4 BR
2 baths
Sleeps 8
Close to Osterville Village!
Close to Osterville Village!
Distance to beach: 1 mile to Dowses Beach - beach sticker included
24 reviews read reviews
Summer:
$4,000 - $4,200/wk
Off Season:
$350 - $575/night
$2,500 - $4,200/wk
4
Osterville
ID 36027
Summer:
$3,360/wk
Off Season:
$260 - $280/night
$2,870 - $3,150/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
Summer:
$2,100 - $2,500/wk
Off Season:
$2,500/wk
3
Osterville
ID 35895
Summer:
$2,450 - $4,600/wk
Off Season:
$300 - $500/night
$2,100 - $2,700/wk
$4,000 - $6,500/mo
3
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
4 reviews read reviews
Summer:
$2,600 - $3,200/wk
Off Season:
$300 - $385/night
$2,200 - $2,500/wk
$8,500 - $10,000/mo
Osterville
ID 37316
Summer:
$7,000/wk
Off Season:
$300 - $600/night
$3,500 - $7,000/wk

Osterville vacation rentals that sleep 7

Osterville
ID 18377
3 BR
1 ½ bath
Sleeps 7
Roomy Osterville Favorite with Private Gated Yard
Roomy Osterville Favorite with Private Gated Yard
Distance to beach: .7 Dowses and 2.3 Craigville Beach
Summer:
$2,695/wk
Off Season:
$300 - $325/night
$2,100 - $2,695/wk
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
31 reviews read reviews
Summer:
$2,650 - $3,300/wk
Off Season:
$1,750 - $2,620/wk
5

Osterville vacation rentals that sleep 6

Osterville
ID 38694
Summer:
$6,300/wk
Off Season:
$500/night
$3,500 - $6,300/wk
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:
$2,500 - $3,200/wk
Off Season:
$275 - $350/night
$1,800 - $2,500/wk
$3,000/mo
7
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
Summer:
$5,000 - $6,000/wk
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
Summer:
$7,500/wk
$30,000 - $37,500/mo
Off Season:
$7,500/wk
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:
$2,000 - $2,100/wk
Off Season:
$175 - $215/night
$1,000 - $2,000/wk
$2,100 - $2,200/mo
6
Osterville
ID 32374
3 BR
2 ½ baths
Sleeps 6
Beautiful & Pristine Osterville Cape, walk to Village
Beautiful & Pristine Osterville Cape, walk to Village
Distance to beach: 1 3/10 miles to Craigville Beach and 1 6/10 miles to Dowses
Summer:
$4,000/wk
Off Season:
$3,500 - $4,000/wk
Osterville
ID 37313
2 BR
2 baths
Sleeps 6
Osterville Oasis
Osterville Oasis
Distance to beach: 2.6 mi to Craigville Beach
Summer:
$4,025 - $4,375/wk
Off Season:
$315/night
$2,450 - $3,150/wk

Osterville vacation rentals that sleep 5

Osterville
ID 37279
3 BR
1 ½ bath
Sleeps 5
Osterville Cape Cod- 3BR & Pet Friendly
Osterville Cape Cod- 3BR & Pet Friendly
Distance to beach: 3.5 miles to Craigville Beach
Summer:
$2,093/wk
Off Season:
$230 - $255/night
$1,610 - $1,900/wk

Osterville vacation rentals that sleep 4

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
5 reviews read reviews
Summer:
$2,500 - $2,950/wk
Off Season:
$2,000 - $2,950/wk
$2,500 - $3,000/mo

Osterville vacation rentals that sleep 3

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
Summer:
$12,250/wk
Off Season:
$650 - $850/night
$6,000 - $12,250/wk