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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.

10 Vacation Properties in Osterville
Sleeps

Osterville vacation rentals that sleep 10

Osterville
ID 33824
Off-season:
$4,500/wk

Osterville vacation rentals that sleep 8

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
21 reviews read reviews
Off-season:
$3,250 - $3,500/wk
Off Season:
$275 - $325/night
$2,200 - $3,400/wk
Osterville
ID 34929
4 BR
3 baths
Sleeps 8
Restful Summer Retreat with Central AC
Restful Summer Retreat with Central AC
Distance to beach: 1.4 mi to Dowses
Off-season:
$5,000/wk
Off Season:
$5,000 - $7,000/wk
Osterville
ID 34142
3 BR
2 ½ baths
Sleeps 8
Osterville gem with A/C & short walk to Joshua's Pond!
Osterville gem with A/C & short walk to Joshua's Pond!
Distance to beach: 3 minute walk to Joshua Pond and Beach Pass included for all Barnstable Beaches/ Dowses
1 review read review
Off-season:
$3,100 - $3,300/wk
Off Season:
$2,300 - $3,000/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
1 review read review
Off-season:
$2,100/wk
Off Season:
$2,100/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: 4/10 mile to Joshua Pond and 1 mile to Dowses
27 reviews read reviews
Off-season:
$1,750 - $2,950/wk
$3,900/mo
Off Season:
$1,650 - $2,400/wk
$3,500/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
Off-season:
$400 - $450/night
$3,500 - $4,500/wk
Off Season:
$400 - $450/night
$3,000 - $4,000/wk

Osterville vacation rentals that sleep 4

Osterville
ID 34597
2 BR
1 bath
Sleeps 4
Little Neck in Oysterville
Little Neck in Oysterville
Distance to beach: 2 mi to Dowses and 2.7 mi to Craigville Beach
Off-season:
$2,950/wk
Off Season:
$175 - $1,900/wk
Osterville
ID 34848
2 BR
2 ½ baths
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
Off-season:
$2,950/wk
Off Season:
$2,950/wk
Osterville
ID 35093
2 BR
2 baths
Sleeps 4
Osterville Village - Brand New 2B/2Ba One Block To Town
Osterville Village - Brand New 2B/2Ba One Block To Town
Distance to beach: 0.5 mi to Joshua Pond and 1.5 mi to Dowses
Off-season:
$2,500/wk
Off Season:
$1,650 - $2,500/wk