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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.

16 Vacation Properties in Osterville
Sleeps
A fee-based feature highlighting availability within the next 4 weeks.

Osterville vacation rentals that sleep 10

Osterville
ID 35972
Summer:
$4,550 - $6,950/wk
Off Season:
$350 - $450/night
$2,500 - $4,550/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
22 reviews read reviews
Summer:
$3,400 - $3,600/wk
Off Season:
$325 - $425/night
$1,800 - $3,400/wk
4
Osterville
ID 34723
4 BR
2 baths
Sleeps 8
JULY 9th available. Pets considered.
JULY 9th available. Pets considered.
Distance to beach: 1 mile Dowses
Summer:
$3,500/wk
Osterville
ID 36027
Summer:
$2,400 - $3,500/wk
Off Season:
$400 - $450/night
$2,400/wk
Osterville
ID 35760
3 BR
2 baths
Sleeps 8
Spacious Osterville Heights Home
Spacious Osterville Heights Home
Distance to beach: 3.4 Miles to Dowses
Summer:
$2,950/wk
Off Season:
$279/night
$1,950/wk
Osterville
ID 35895
3 BR
2 ½ baths
Sleeps 8
Osterville~Newly Renovated 3BR,2.5BA w/AC near Joshua Pond
Osterville~Newly Renovated 3BR,2.5BA w/AC near Joshua Pond
Distance to beach: 3/10 mi to Joshua Pond
3 reviews read reviews
OWNER SPECIAL:
Brand new to rental market June availability weeks and long weekends 6/18/.
Summer:
$3,700 - $4,000/wk
Off Season:
$325 - $500/night
$1,800 - $4,000/wk
3
Osterville
ID 36324
3 BR
2 ½ baths
Sleeps 8
Osterville Village Beauty on 6 Acres of Privacy
Osterville Village Beauty on 6 Acres of Privacy
Distance to beach: 1 mi to Joshua Pond and 1 mi to Dowses
LAST MINUTE ALERT 7/9 - 7/16
OWNER SPECIAL:
Newly listed discounted to $6000/wk for rest of summer $700/nt weekdays and $1200/nt weekends.
Summer:
$700 - $1,200/night
$5,000 - $8,500/wk
$20,000/mo
Off Season:
$400 - $750/night
$2,000 - $7,000/wk
$4,000 - $15,000/mo
2
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
Summer:
$2,100 - $2,500/wk
Off Season:
$2,100/wk
3

Osterville vacation rentals that sleep 7

Osterville
ID 23526
3 BR
2 baths
Sleeps 7
Spacious Cape Cottage with New Kitchen and Bathrooms
Spacious Cape Cottage with New Kitchen and Bathrooms
Distance to beach: 4/10 mile to Joshua Pond and 1 mile to Dowses
28 reviews read reviews
Summer:
$2,940 - $2,950/wk
Off Season:
$1,750 - $2,400/wk
$3,900/mo
4

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:
$3,500/wk
Off Season:
$500/night
$3,500/wk
Osterville Woods
ID 35272
Summer:
$2,300 - $3,200/wk
Off Season:
$225 - $250/night
$1,800 - $2,300/wk
$2,250/mo
2

Osterville vacation rentals that sleep 5

Close to Town Centre
ID 35847
2 BR
2 baths
Sleeps 5
New Listing in Charming Osterville - Calendar Open
New Listing in Charming Osterville - Calendar Open
Distance to beach: 1.2 miles Joshua Pond and 1.5 miles Dowses
OWNER SPECIAL:
10% Discount.
Summer:
$2,750 - $2,950/wk
$10,000/mo
Off Season:
$1,500 - $2,750/wk
$2,500 - $10,000/mo
5
Osterville
ID 36265
2 BR
1 bath
Sleeps 5
Renovated Osterville Cottage near Joshua Pond, Beach
Renovated Osterville Cottage near Joshua Pond, Beach
Distance to beach: 2/10 mi to Joshua Pond and 1.9 mi to Dowses
Summer:
$1,323 - $2,303/wk
Off Season:
$169 - $299/night
$1,303 - $2,113/wk
2

Osterville vacation rentals that sleep 4

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
Summer:
$1,500 - $2,950/wk
Off Season:
$1,500/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
Summer:
$1,500 - $2,950/wk
Off Season:
$1,500/wk

Osterville vacation rentals that sleep 2

Osterville
ID 36362
1 BR
1 bath
Sleeps 2
Hidden Gem Studio in Heart of Osterville Village
Hidden Gem Studio in Heart of Osterville Village
Distance to beach: 0.6 mi to Joshua Pond and 1.7 mi to Dowses
Summer:
$1,250/wk
Off Season:
$1,250/wk