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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.

7 Vacation Properties in Osterville
Sleeps

Osterville vacation rentals that sleep 10

Osterville
ID 30082
5 BR
3 baths
Sleeps 10
RELAX IN OSTERVILLE, MA! (Beach Pass, Fire Pit, etc..)
RELAX IN OSTERVILLE, MA! (Beach Pass, Fire Pit, etc..)
Distance to beach: Dowses Beach- 1.7 mi & Craigville Beach- 2.8 mi
1 review read review
Summer:
$3,370 - $3,855/wk
Off Season:
$375/night
$2,600/wk
Osterville
ID 31391
Summer:
$3,000 - $3,800/wk
Off Season:
$200 - $400/night
$1,000 - $3,000/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
Off Season:
$5,100/wk

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
11 reviews read reviews
Summer:
$2,700 - $2,900/wk
Off Season:
$250 - $300/night
$1,200 - $2,900/wk
Osterville
ID 27235
Off Season:
$1,500 - $3,000/wk

Osterville vacation rentals that sleep 7

Osterville
ID 19650
3 BR
2 baths
Sleeps 7
Spacious Family Getaway Home
Spacious Family Getaway Home
Distance to beach: 2 miles Dowses Beach
9 reviews read reviews
Summer:
$1,750/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
Off Season:
$2,700/wk