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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.

11 Vacation Properties in Osterville
Sleeps

Osterville vacation rentals that sleep 12

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:
$18,000/wk
Off Season:
$10,000 - $18,000/wk

Osterville vacation rentals that sleep 10

Osterville
ID 35972
Summer:
$4,550 - $6,950/wk
Off Season:
$350 - $450/night
$2,500 - $5,950/wk
$3,500 - $4,500/mo
2

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
23 reviews read reviews
Summer:
$3,500 - $3,600/wk
Off Season:
$1,800 - $3,600/wk
4
Osterville
ID 35895
Summer:
$4,000 - $4,500/wk
Off Season:
$425 - $500/night
$1,800 - $4,500/wk
3
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
3

Osterville vacation rentals that sleep 7

Osterville
ID 23526
3 BR
2 baths
Sleeps 7
Spacious, Renovated Cape. Walk to Main St. and a Swim!
Spacious, Renovated Cape. Walk to Main St. and a Swim!
Distance to beach: 4/10 mile to Joshua Pond and 1 mile to Dowses
29 reviews read reviews
Summer:
$3,220/wk
Off Season:
$1,750 - $2,620/wk
$3,900/mo
4

Osterville vacation rentals that sleep 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:
$3,500/wk
Off Season:
$500/night
$3,500/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:
$3,200/wk
Off Season:
$275 - $400/night
$1,800 - $2,800/wk
$2,250/mo
3

Osterville vacation rentals that sleep 5

Close to Town Centre
ID 35847
2 BR
2 baths
Sleeps 5
New Listing in Charming Osterville - Seasonal Rentals
New Listing in Charming Osterville - Seasonal Rentals
Distance to beach: 1.2 miles Joshua Pond and 1.5 miles Dowses
Summer:
$2,750 - $2,950/wk
$11,000/mo
Off Season:
$1,500 - $3,000/wk
$3,000 - $10,000/mo
5

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
3 reviews read reviews
Summer:
$2,695 - $2,750/wk
Off Season:
$1,500 - $2,750/wk
$2,250 - $4,000/mo
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
1 review read review
Summer:
$1,695 - $2,750/wk
Off Season:
$1,200 - $2,500/wk
$2,250/mo