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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

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

Osterville

ID 35972

4 BR

2 ½ baths

Sleeps 10

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

Osterville

ID 37082

4 BR

3 ½ baths

Sleeps 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

OWNER SPECIAL:

June weeks available for the 2025 summer season.

Summer:
$8,750/wk

Off Season:
$5,250 - $8,750/wk

Osterville

ID 39748

4 BR

3 baths

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

Osterville vacation rentals that sleep 9

Osterville

ID 38500

4 BR

3 ½ 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

Summer:
$5,000 - $5,500/wk

Off Season:
$350 - $400/night
$2,500 - $5,500/wk

Osterville - Barnstable

ID 36837

3 BR

2 baths

Sleeps 9

Cape Escape with Beach pass- Summer 2025 Bookings Now 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

Osterville vacation rentals that sleep 8

Osterville

ID 40209

4 BR

2 ½ baths

Sleeps 8

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

Distance to beach: 1.6 mi to Dowses

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

Distance to beach: 1.2 mi to Joshua Pond

Summer:
$14,000/wk

Osterville

ID 10157

3 BR

2 baths

Sleeps 8

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

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

Summer:
$2,650/wk

Osterville

ID 37412

3 BR

2 baths

Sleeps 8

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 vacation rentals that sleep 7

Osterville

ID 18377

3 BR

1 ½ bath

Sleeps 7

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
$2,200 - $3,100/wk

Osterville

ID 23526

3 BR

2 baths

Sleeps 7

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

Osterville Barnstable

ID 19650

3 BR

2 baths

Sleeps 7

Spacious Family Getaway Home

Distance to beach: 2 1/2 Craigville Beach and 2 miles Dowses Beach

5.013 reviews

Summer:
$2,100 - $2,300/wk
$10,600/mo

Off Season:
$295 - $350/night
$2,000 - $2,100/wk

Osterville

ID 40190

3 BR

2 ½ baths

Sleeps 7

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 vacation rentals that sleep 6

Osterville Woods

ID 35272

3 BR

3 baths

Sleeps 6

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

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

Summer:
$5,000 - $6,000/wk

Off Season:
$3,000 - $6,000/wk

Osterville

ID 38319

3 BR

2 baths

Sleeps 6

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/mo

Osterville

ID 39880

3 BR

2 baths

Sleeps 6

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

Osterville

ID 40211

3 BR

2 baths

Sleeps 6

Sought after Wianno Circle area home close to Dowses beach R

Distance to beach: 0.9 mi to Dowses

Summer:
$3,304/wk

Off Season:
$3,304/wk

Osterville

ID 40218

3 BR

2 baths

Sleeps 6

Private beach. Seaside cottage RPMS109

Distance to beach: 0.5 mi to Dowses

Summer:
$7,651/wk

Off Season:
$7,651/wk

Osterville vacation rentals that sleep 4

Osterville

ID 34848

2 BR

1 ½ 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:
$2,395 - $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

Distance to beach: 0.7 mi to Joshua Pond

Summer:
$1,904/wk

Off Season:
$1,904/wk