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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.

9 Vacation Properties in Osterville
Sleeps

Osterville vacation rentals that sleep 10

Osterville
ID 30082
5 BR
3 baths
Sleeps 10
Cape House for Large Group or Family!!
Cape House for Large Group or Family!!
Distance to beach: Dowses Beach- 1.7 mi & Craigville Beach- 2.8 mi
Summer:
$2,600 - $3,300/wk
Off Season:
$375/night
$2,600/wk
Osterville
ID 22183
3 BR
4 ½ baths
Sleeps 10
Beautiful Little Island Home with Fenced in Yard
Beautiful Little Island Home with Fenced in Yard
Distance to beach: Dowses Beach is about 2 miles away
Summer:
$6,500 - $8,001/wk
Off Season:
$5,100 - $6,500/wk

Osterville vacation rentals that sleep 9

Osterville
ID 27473
4 BR
2 baths
Sleeps 9
Recently renovated home, steps to Osterville Village!
Recently renovated home, steps to Osterville Village!
Distance to beach: 1 mile to Dowses Beach - beach sticker included
6 reviews read reviews
Summer:
$2,800 - $2,900/wk
Off Season:
$250 - $300/night
$2,100 - $2,700/wk

Osterville vacation rentals that sleep 8

Osterville
ID 30162
5 BR
3 baths
Sleeps 8
Outstanding Osterville Location!
Outstanding Osterville Location!
Distance to beach: Beautiful Dowses beach is 9/10 mile away
Summer:
$550/night
$2,500 - $4,200/wk
Off Season:
$375/night
$2,500 - $2,800/wk
Osterville
ID 14924
4 BR
2 ½ baths
Sleeps 8
Charming, Fully-Appointed 4 Bedroom Home, Minutes from Beach
Charming, Fully-Appointed 4 Bedroom Home, Minutes from Beach
Distance to beach: 2.5 miles to Dowses Beach- beach sticker included
5 reviews read reviews
Summer:
$2,800 - $3,000/wk
$11,000/mo
Off Season:
$2,800 - $3,000/wk
$11,000/mo
Osterville
ID 27235
Summer:
$2,500 - $3,000/wk
Off Season:
$400 - $500/night
$1,500 - $3,000/wk
Osterville
ID 29488
3 BR
1 ½ bath
Sleeps 8
3 BR, Remodeled, Central AC, Beach Pass WR#134586
3 BR, Remodeled, Central AC, Beach Pass WR#134586
Distance to beach: over 1 mile to Dowses Beach
Summer:
$1,675 - $2,350/wk
Off Season:
$1,495 - $1,675/wk

Osterville vacation rentals that sleep 6

Osterville
ID 19974
3 BR
2 ½ baths
Sleeps 6
Walk to Quaint Osterville Village!
Walk to Quaint Osterville Village!
Distance to beach: 1/2 mile to Dowse's Beach
3 reviews read reviews
Summer:
$2,700/wk
$10,000 - $110,000/mo
Off Season:
$2,600 - $2,700/wk

Osterville vacation rentals that sleep 5

Osterville
ID 24515
Summer:
$395/night
$2,500/wk
Off Season:
$395/night
$1,850 - $2,500/wk
$7,200 - $7,400/mo