Osterville
ID 41425
- 6 BR
- 5 baths
- Sleeps 12
Just listed. Renovated luxury rental with pool in Oyster Ha
Distance to beach: 2.7 mi to Joshua Pond
Summer:
$27,539/wk
Off Season:
$27,539/wk
Osterville Vacation Rentals
19 properties
Osterville vacation rentals that sleep 12
Osterville
ID 37621
- 5 BR
- 6 baths
- Sleeps 12
Luxury Property On Gated Grand Island With Pool! (2300)
Distance to beach: 3.3 mi to Joshua Pond
Summer:
$2,878 - $3,592/night
$21,028 - $26,212/wk
Off Season:
$2,163 - $2,878/night
$15,838 - $21,028/wk
Osterville vacation rentals that sleep 10
Osterville/ Centerville Line
ID 39006
- 5 BR
- 3 baths
- Sleeps 10
Cape Cod Summer Estate | Pool + Firepit + Family Retreat
Distance to beach: 1.4 mi to Joshua Pond and 2.4 mi Dowses
Off Season:
$1,170 - $1,430/night
$8,650 - $12,150/wk
2
Osterville
ID 41432
- 5 BR
- 4 baths
- Sleeps 10
Amazing Waterfront 5BD--Private Setting, Infinity Pool
Distance to beach: 1.5 Joshua Pond and 2.5 miles Dowses
Off Season:
$9,000 - $12,500/wk
Osterville
ID 35972
- 4 BR
- 2 baths
- Sleeps 10
Osterville retreat - now booking in 2026!
Distance to beach: 2.4 mi to Dowses
4.911 reviews
Off Season:
$3,450 - $4,450/wk
$3,000 - $3,500/mo
2
Osterville vacation rentals that sleep 9
Osterville
ID 38500
- 4 BR
- 3 baths
- Sleeps 9
Private Oasis: Elegant Comfort & Free Beach Pass
Distance to beach: 2.9 mi to Dowses and 4.9 mi to Craigville Beach
5.01 review
Off Season:
$500/night
$3,300 - $5,300/wk
$6,000 - $7,000/mo
3
Osterville vacation rentals that sleep 8
Osterville
ID 40228
- 4 BR
- 3 baths
- Sleeps 8
Osterville heated pool rental near Dowses beach RPMS102
Distance to beach: 1.2 mi to Joshua Pond
Off Season:
$15,479/wk
Osterville
ID 41676
- 4 BR
- 2 baths
- Sleeps 8
New for 2026. Great Osterville location! RPMS167
Distance to beach: 1.6 mi to Joshua Pond and 1.6 mi to Dowses
Summer:
$543/night
$3,942/wk
Off Season:
$3,840 - $3,942/wk
Osterville
ID 42250
- 3 BR
- 2 baths
- Sleeps 8
Tucked Away in Osterville
Distance to beach: 1.6 mi to Joshua's Pond Joshua Pond and 1.5 mi to Dowses & Craigville Beaches Dowses
OWNER SPECIAL:
Winter Rental Special Near Osterville Village & Beaches; Available for Summer 2027.
Summer:
$5,000 - $6,500/wk
$23,000 - $32,500/mo
Off Season:
$400 - $650/night
$2,100 - $4,500/wk
$3,700 - $4,100/mo
3
Osterville
ID 34432
- 3 BR
- 2 baths
- Sleeps 8
Updated 3 Bedroom with AC & Great Proximity to Summer Fun
Distance to beach: 1.2 mi to Dowses and 3.5 mi Craigville Beach
5.04 reviews
3
Osterville vacation rentals that sleep 7
Osterville
ID 23526
- 3 BR
- 2 baths
- Sleeps 7
Charming Garden and New Patio. Walk to Main St. and a Swim!
Distance to beach: 3/10 mile to Joshua Pond and 1 mile to Dowses
5.038 reviews
Summer:
$3,850/wk
Off Season:
$2,320 - $3,136/wk
6
Osterville
ID 18377
- 3 BR
- 1 bath
- Sleeps 7
Roomy Osterville Favorite with Private Gated Yard
Distance to beach: .7 Dowses and 2.3 Craigville Beach
Off Season:
$300 - $400/night
$2,300/wk
$4,000 - $5,000/mo
Osterville vacation rentals that sleep 6
Osterville
ID 42262
- 4 BR
- 3 baths
- Sleeps 6
Your Private Osterville Summer Oasis Awaits! RPMS012
Distance to beach: 1.0 mi to Joshua Pond
Summer:
$13,384/wk
Off Season:
$10,269 - $11,308/wk
Osterville Woods
ID 35272
Summer:
$2,850 - $3,000/wk
Off Season:
$230/night
$2,050 - $2,550/wk
$3,000/mo
6
Osterville
ID 39880
- 3 BR
- 2 baths
- Sleeps 6
Summer Time Fun - Osterville Retreat with Beach Pass
Distance to beach: 1.3 mi to Joshua Pond and 2 miles Dowses
4.54 reviews
Summer:
$400/night
$2,925/wk
Off Season:
$325/night
$2,125 - $2,400/wk
3
Osterville
ID 36955
- 3 BR
- 2 baths
- Sleeps 6
Spacious Home/Walk to Town/Beach Pass & Kayaks Included
Distance to beach: 1.0 mi to Dowses and 1.0 mi to Craigville Beach
Off Season:
$3,475 - $6,475/wk
2
Osterville vacation rentals that sleep 5
Osterville Village (Wianno Ave
ID 27783
- 2 BR
- 1 bath
- Sleeps 5
WINTER RENTAL in Osterville Village (also 2027 summer)
Distance to beach: .9 miles to Dowses and 3.4 miles Craigville Beach
Off Season:
$2,400/mo
5
Osterville vacation rentals that sleep 4
Osterville
ID 34848
- 2 BR
- 1 bath
- Sleeps 4
Enchanting Cottage - one block to Osterville Village!
Distance to beach: 0.5 mi to Joshua Pond and 1.5 mi to Dowses
5.07 reviews
Summer:
$2,700/wk
Off Season:
$1,950 - $2,700/wk
$2,500 - $3,500/mo
Osterville vacation rentals that sleep 3
Osterville
ID 40214
- 2 BR
- 1 bath
- Sleeps 3
Charming cottage near Osterville Village and Dowses beach RP
Distance to beach: 0.7 mi to Joshua Pond
Summer:
$2,777/wk
Off Season:
$2,777/wk