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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.

26 Vacation Properties in Osterville
Sleeps

Osterville vacation rentals that sleep 14

Osterville
ID 37315
7 BR
5 ½ baths
Sleeps 14
Impressive Osterville Residence - w/Guest House
Impressive Osterville Residence - w/Guest House
Distance to beach:
OWNER SPECIAL:
Price reduced by $3,000/week for July and August availability!
Summer:
$9,500 - $15,000/wk
Off Season:
$9,500/wk

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
ID 37621
Summer:
$16,999 - $18,000/wk
Off Season:
$15,000 - $16,000/wk
Osterville
ID 37106
Summer:
$14,700/wk
Off Season:
$1,200/night
$8,400 - $14,700/wk

Osterville vacation rentals that sleep 10

Osterville
ID 35972
Summer:
$4,000 - $5,950/wk
Off Season:
$350 - $450/night
$4,000 - $5,950/wk
$3,500 - $4,500/mo
2
Osterville
ID 37082
4 BR
3 ½ baths
Sleeps 10
Newly Renovated Osterville Luxury Home Near Village
Newly Renovated Osterville Luxury Home Near Village
Distance to beach: 1/2 mi to Joshua Pond and 2 mi to Dowses
1 review read review
OWNER SPECIAL:
Brand new with beach pass!!!
Summer:
$7,500/wk
Off Season:
$7,500/wk
2
Osterville
ID 37314
4 BR
4 ½ baths
Sleeps 10
Sea View Ave - New Construction - Pool Hot Tub Tennis Court
Sea View Ave - New Construction - Pool Hot Tub Tennis Court
Distance to beach: 0.25 mi to Dowses
OWNER SPECIAL:
Reduced to a 3 night minimum over July 4th week!
Summer:
$7,000/night
$30,000/wk
Off Season:
$22,000 - $25,000/wk
Osterville
ID 37643
4 BR
4 baths
Sleeps 10
Large 5BD, 4BTH Waterfront Home with Deep Water Dock
Large 5BD, 4BTH Waterfront Home with Deep Water Dock
Distance to beach: Waterfront with Deep Water Dock
Summer:
$8,500 - $10,000/wk
Off Season:
$7,000 - $8,500/wk
Osterville
ID 37723
Summer:
$650 - $750/night
$5,075/wk
Off Season:
$5,075/wk
4

Osterville vacation rentals that sleep 9

Osterville - Barnstable
ID 36837
3 BR
2 baths
Sleeps 9
Cape Escape - Minutes to Beaches w Barnstable Beach Pass
Cape Escape - Minutes to Beaches w Barnstable Beach Pass
Distance to beach: 1/2 mile Joshua Pond and 2 miles Dowses
2 reviews read reviews
Summer:
$2,500 - $3,200/wk
$12,000/mo
Off Season:
$350 - $400/night
$2,000 - $2,500/wk
$8,000 - $10,000/mo
2
Osterville
ID 36955
3 BR
2 baths
Sleeps 9
Spacious Home/Walk to Town/Beach Pass & Kayaks Included
Spacious Home/Walk to Town/Beach Pass & Kayaks Included
Distance to beach: 1.0 mi to Dowses and 1.0 mi to Craigville Beach
Summer:
$5,000 - $6,000/wk
Off Season:
$4,000 - $5,000/wk
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:
$3,600 - $3,700/wk
Off Season:
$2,200 - $3,600/wk
4
Osterville
ID 37646
4 BR
3 baths
Sleeps 8
Luxurious Osterville Oasis/Heated Pool
Luxurious Osterville Oasis/Heated Pool
Distance to beach: 0.6 mi to Joshua Pond and Dowses Beach 2.5 mi.
Summer:
$7,500/wk
$30,000 - $37,500/mo
Off Season:
$500 - $785/night
$5,500/wk
$22,000/mo
Osterville
ID 10157
3 BR
2 baths
Sleeps 8
Osterville Three Bedroom Cape
Osterville Three Bedroom Cape
Distance to beach: 1 3/4 miles to famous Dowses private beach
Summer:
$2,600/wk
Off Season:
$250 - $350/night
$1,850 - $2,600/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
4 reviews read reviews
Summer:
$2,500/wk
Off Season:
$1,000/wk
3
Osterville
ID 35895
3 BR
2 ½ baths
Sleeps 8
Osterville- New renovation, central AC, beach pass included
Osterville- New renovation, central AC, beach pass included
Distance to beach: 3/10 mi to Joshua Pond
10 reviews read reviews
OWNER SPECIAL:
New availability and price reduction for the 2nd week of June. Minimum stay is two nights.
Summer:
$4,000 - $4,500/wk
$16,000 - $17,000/mo
Off Season:
$255 - $530/night
$1,800 - $3,700/wk
$4,000 - $6,500/mo
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
Summer:
$750 - $1,500/night
$6,000 - $7,500/wk
$30,000/mo
Off Season:
$300 - $750/night
$2,000 - $5,000/wk
$3,500 - $12,000/mo
2
Osterville
ID 37316
3 BR
1 ½ bath
Sleeps 8
Osterville Village - Large Yard & Outdoor Patio
Osterville Village - Large Yard & Outdoor Patio
Distance to beach: 1 mile to Dowses
OWNER SPECIAL:
Price reduced by $200/night for all summer 2023 availability!
Summer:
$950/night
$6,496/wk
Off Season:
$300 - $600/night
$3,500 - $6,496/wk
Osterville
ID 37412
3 BR
2 baths
Sleeps 8
Pristine Family Vacation Home/Beach Pass Included
Pristine Family Vacation Home/Beach Pass Included
Distance to beach: 1.8 mi to Joshua Pond and 3.2 Dowses
2 reviews read reviews
OWNER SPECIAL:
20% Off In June 2023 Bookings.
Summer:
$3,000 - $3,200/wk
$12,000 - $15,000/mo
Off Season:
$300 - $385/night
$2,000 - $3,000/wk
$7,000 - $10,000/mo

Osterville vacation rentals that sleep 7

Osterville
ID 23526
3 BR
2 baths
Sleeps 7
Delightful Osterville Haven. Walk to Main St. and a Swim!
Delightful Osterville Haven. Walk to Main St. and a Swim!
Distance to beach: 3/10 mile to Joshua Pond and 1 mile to Dowses
29 reviews read reviews
OWNER SPECIAL:
The weeks of June 24, July 1 and July 15 are discounted from $3220 to $3000.
Summer:
$2,990 - $3,220/wk
Off Season:
$1,750 - $2,620/wk
5

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:
$3,000 - $3,500/wk
Off Season:
$500/night
$3,000 - $3,500/wk
Osterville
ID 37313
2 BR
2 baths
Sleeps 6
The Cape Escape
The Cape Escape
Distance to beach: 2.6 mi to Craigville Beach
Summer:
$4,500 - $4,750/wk
Off Season:
$300 - $450/night
$3,000 - $4,500/wk

Osterville vacation rentals that sleep 5

Osterville
ID 37279
3 BR
1 ½ bath
Sleeps 5
Osterville Cape Cod- 3BR & Pet Friendly
Osterville Cape Cod- 3BR & Pet Friendly
Distance to beach: 3.5 miles to Craigville Beach
Summer:
$1,890/wk
Off Season:
$240 - $255/night
$1,680 - $1,890/wk

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
4 reviews read reviews
Summer:
$2,695 - $2,950/wk
Off Season:
$1,395 - $2,195/wk
$4,000/mo
Osterville
ID 37513
2 BR
1 bath
Sleeps 4
Lovely Cottage Steps to Village and near Dowses Beach!
Lovely Cottage Steps to Village and near Dowses Beach!
Distance to beach: 7/10 mi to Dowses and Less than a mile to Dowses beach.
Summer:
$1,900/wk
Off Season:
$1,900/wk

Osterville vacation rentals that sleep 3

Osterville
ID 37628
3 BR
3 ½ baths
Sleeps 3
Charming Osterville Home w/ Pool - Near Town
Charming Osterville Home w/ Pool - Near Town
Distance to beach: 600 ft to Joshua Pond and 1.5 mi to Dowses
OWNER SPECIAL:
Price reduced by $2,500/week for all 2023 availability!
Summer:
$9,000 - $11,500/wk
Off Season:
$1,400/night
$9,000/wk