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Mid Cape Cod Vacation Rentals

Osterville Vacation Rentals

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.

24 properties
Osterville Guide

Osterville vacation rentals that sleep 10
Osterville/ Centerville Line
ID 39006
5 BR
3 baths
Sleeps 10
* New 2024* Luxury Coastal Retreat w/ Heated Saltwater Pool
* New 2024* Luxury Coastal Retreat w/ Heated Saltwater Pool
Distance to beach: 1.4 mi to Joshua Pond and 2.4 mi Dowses
Summer:
 $11,500 - $12,500/wk
Off Season:
 $1,072 - $1,500/night
 $7,000 - $12,500/wk
2
Osterville
ID 35972
4 BR
2 ½ baths
Sleeps 10
2 summer weeks left! - Osterville retreat
2 summer weeks left! - Osterville retreat
Distance to beach: 2.4 mi to Dowses
4.99 reviews
Summer:
 $3,950/wk
Off Season:
 $350 - $450/night
 $3,950/wk
 $3,000 - $3,500/mo
2
Osterville
ID 37082
4 BR
3 ½ baths
Sleeps 10
Seasons by the Sea-newly renovated home sleeps up to 10
Seasons by the Sea-newly renovated home sleeps up to 10
Distance to beach: 1/2 mi to Joshua Pond and 2 mi to Dowses
5.04 reviews
Summer:
 $8,750/wk
Off Season:
 $5,250 - $8,750/wk
4
Osterville
ID 39748
4 BR
3 baths
Sleeps 10
Quintessential Home Walk to Joshua's Pond Sleeps 10
Quintessential Home Walk to Joshua's Pond Sleeps 10
Distance to beach: 0.3 mi to Joshua Pond and 2 mi to Dowses
Summer:
 $7,000 - $8,200/wk
Off Season:
 $495 - $849/night
 $3,465 - $8,200/wk
5

Osterville vacation rentals that sleep 9
Osterville
ID 38500
4 BR
3 ½ baths
Sleeps 9
Private Oasis: Elegant Comfort & Free Beach Pass
Private Oasis: Elegant Comfort & Free Beach Pass
Distance to beach: 2.9 mi to Dowses and 4.9 mi to Craigville Beach
OWNER SPECIAL:
Discounted to $5k for peak summer weeks! Close to Osterville Village & beaches! 2 primary suites!
Summer:
 $5,000 - $5,500/wk
Off Season:
 $350 - $400/night
 $2,500 - $5,500/wk
3
Osterville - Barnstable
ID 36837
3 BR
2 baths
Sleeps 9
Cape Escape with Beach pass- July 5th week is open!
Cape Escape with Beach pass- July 5th week is open!
Distance to beach: 1/2 mile Joshua Pond and 2 miles Dowses
5.05 reviews
Summer:
 $2,500 - $3,300/wk
 $10,000 - $13,000/mo
Off Season:
 $400 - $589/night
 $1,500 - $2,500/wk
 $4,000 - $6,500/mo
2

Osterville vacation rentals that sleep 8
Osterville
ID 40209
4 BR
2 ½ baths
Sleeps 8
Welcome to the Birds Nest RPMS032
Welcome to the Birds Nest RPMS032
Distance to beach: 1.1 mi to Joshua Pond
Summer:
 $4,501 - $6,300/wk
Off Season:
 $4,501 - $6,300/wk
Osterville
ID 40223
4 BR
4 ½ baths
Sleeps 8
Heated pool, close to beach. RPMS125
Heated pool, close to beach. RPMS125
Distance to beach: 1.6 mi to Dowses
1 review
Summer:
 $13,006/wk
Off Season:
 $13,006/wk
Osterville
ID 40228
4 BR
3 ½ baths
Sleeps 8
NEW for 2025! Osterville heated pool rental near Dowses be
NEW for 2025! Osterville heated pool rental near Dowses be
Distance to beach: 1.2 mi to Joshua Pond
Summer:
 $14,000/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
5.04 reviews
Summer:
 $2,650/wk
3
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
5.06 reviews
Summer:
 $2,400 - $3,200/wk
Off Season:
 $315 - $370/night
 $2,200 - $2,400/wk
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:
 $2,175 - $2,300/wk
Off Season:
 $225 - $275/night
 $1,850 - $2,300/wk

Osterville vacation rentals that sleep 7
Osterville
ID 18377
3 BR
1 ½ bath
Sleeps 7
Roomy Osterville Favorite with Private Gated Yard
Roomy Osterville Favorite with Private Gated Yard
Distance to beach: .7 Dowses and 2.3 Craigville Beach
Summer:
 $1,200 - $3,100/wk
Off Season:
 $300 - $325/night
 $2,000 - $3,100/wk
Osterville Barnstable
ID 19650
3 BR
2 baths
Sleeps 7
Spacious Family Getaway Home
Spacious Family Getaway Home
Distance to beach: 2 1/2 Craigville Beach and 2 miles Dowses Beach
5.013 reviews
Summer:
 $2,100 - $2,500/wk
 $10,600/mo
Off Season:
 $295 - $350/night
 $2,000 - $2,100/wk
7
Osterville
ID 40190
3 BR
2 ½ baths
Sleeps 7
Oasis in Osterville
Oasis in Osterville
Distance to beach: 1.5 mi to Hamblin Pond and 3.2 mi Dowses
Summer:
 $400/night
 $2,500 - $2,800/wk
Off Season:
 $285/night
 $2,000/wk
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
5.035 reviews
Summer:
 $3,077 - $3,355/wk
Off Season:
 $1,780 - $2,696/wk
6

Osterville vacation rentals that sleep 6
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:
 $2,200 - $3,200/wk
Off Season:
 $225 - $230/night
 $2,000 - $2,850/wk
 $2,500 - $3,000/mo
6
Osterville
ID 38319
3 BR
2 baths
Sleeps 6
Dog Friendly Charmer - Convenient Location
Dog Friendly Charmer - Convenient Location
Distance to beach: 1.6 miles Joshua Pond and 3.0 miles Dowses
Summer:
 $1,800/wk
Off Season:
 $220/night
 $1,500 - $1,800/wk
 $2,000 - $3,200/mo
5
Osterville
ID 39880
3 BR
2 baths
Sleeps 6
Cozy Osterville Retreat with Beach Pass
Cozy Osterville Retreat with Beach Pass
Distance to beach: 1.3 mi to Joshua Pond and 2 miles Dowses
OWNER SPECIAL:
Book a week in May or June and save $75 per week!
Summer:
 $2,150 - $2,975/wk
 $11,000 - $13,000/mo
Off Season:
 $2,100 - $2,975/wk
 $10,000/mo
3
Osterville
ID 40211
3 BR
2 baths
Sleeps 6
Sought after Wianno Circle area home close to Dowses beach R
Sought after Wianno Circle area home close to Dowses beach R
Distance to beach: 0.9 mi to Dowses
1 review
Summer:
 $3,304/wk
Off Season:
 $3,304/wk
Osterville
ID 40218
3 BR
2 baths
Sleeps 6
Private beach. Seaside cottage RPMS109
Private beach. Seaside cottage RPMS109
Distance to beach: 0.5 mi to Dowses
Summer:
 $7,651/wk
Off Season:
 $7,651/wk
Osterville
ID 36955
3 BR
2 baths
Sleeps 6
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:
 $3,000 - $6,000/wk
2

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
5.07 reviews
Summer:
 $2,395 - $2,500/wk
Off Season:
 $1,975 - $2,395/wk
 $2,500 - $3,500/mo
Osterville
ID 40214
2 BR
1 bath
Sleeps 4
Charming cottage steps to Osterville village. Near Dowses b
Charming cottage steps to Osterville village. Near Dowses b
Distance to beach: 0.7 mi to Joshua Pond
Summer:
 $1,904/wk
Off Season:
 $1,904/wk