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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 9

Osterville (In town)
ID 13933
Summer:
$300 - $350/night
$2,100 - $2,625/wk
$9,000/mo
Off Season:
$200 - $250/night
$1,750 - $2,450/wk
$4,000 - $5,000/mo

Osterville vacation rentals that sleep 8

Osterville
ID 27473
4 BR
2 baths
Sleeps 8
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
12 reviews read reviews
Summer:
$2,900/wk
Off Season:
$250 - $300/night
$1,500 - $2,900/wk
Osterville Woods, Osterville
ID 32073
4 BR
2 baths
Sleeps 8
Ideal Osterville Vacation Home W/Ac, Ocean & Pond Beach Pass
Ideal Osterville Vacation Home W/Ac, Ocean & Pond Beach Pass
Distance to beach: 1.8 mi to Joshua Pond and 3.8 mi to Dowses
Summer:
$2,975/wk
Off Season:
$2,400 - $2,975/wk
Osterville
ID 27235
Summer:
$2,500 - $3,000/wk
Osterville
ID 31391
Summer:
$500 - $650/night
$2,500 - $3,800/wk
Off Season:
$200 - $400/night
$1,400 - $3,000/wk
Osterville
ID 24368
Summer:
$300 - $400/night
$2,750/wk
Off Season:
$150 - $200/night
$1,000/wk

Osterville vacation rentals that sleep 7

Osterville
ID 23526
3 BR
2 baths
Sleeps 7
Spacious Cape Cottage with English-Style Garden
Spacious Cape Cottage with English-Style Garden
Distance to beach: Joshua's Pond (400 ft.) and Dowses Beach (1 mile)
19 reviews read reviews
Summer:
$1,440 - $2,500/wk
$10,300 - $11,000/mo
Off Season:
$206 - $296/night
$1,440 - $2,000/wk
$3,100 - $8,200/mo

Osterville vacation rentals that sleep 6

Osterville
ID 32374
3 BR
2 ½ baths
Sleeps 6
Renovated Osterville Cape w/AC, 2 1/2 Baths, Near Village
Renovated Osterville Cape w/AC, 2 1/2 Baths, Near Village
Distance to beach: 1 3/10 miles to Craigville Beach and 1 6/10 miles to Dowses
Summer:
$2,200 - $2,400/wk
Off Season:
$300/night
$2,100 - $2,400/wk
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
Off Season:
$2,500 - $2,700/wk