Osterville Vacation Rentals
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62 rentals in Osterville.
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Charming Cottage Getaway
Rental Home
2 bedrooms
1 bathroom
Sleeps 3
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Beautiful Osterville Home central to everything!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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*Heated Priv. Pool, Walk to beach & shops, Fully Renovated house
Rental Home
4 bedrooms
4 bathrooms
Sleeps 11
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Osterville Cape Cod-Style Home - One Block from North Bay!
Rental Home
5 bedrooms
6 bathrooms
Sleeps 10
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Cape Cod Family Retreat
Rental Home
12 bedrooms
8 bathrooms
Sleeps 12
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"The Half Shell" Cottage in Osterville Village
Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
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Enjoy & Relax! Beach Pass, Fire Pit, Osterville, MA! Cape Cod⚓️- Sleeps 10!
Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
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Osterville Charmer in a private neighborhood setting
Rental Home
1 bedroom
2 bathrooms
Sleeps 3
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271 Westwind Cir
Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
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THREE BEDROOM CAPE NEAR PRIVATE SWIMMING POND
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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OSTERVILLE, NORTH BAY WITH PRIVATE BEACH AND DOCK
Rental Home
5 bedrooms
7 bathrooms
Sleeps 6
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"Little Neck" Cottage just 3 minutes to Dowses Beach and downtown Osterville
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Perfect Vacation Getaway!
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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Wonderful Classic Cape Cod SummerHome with spectacular Water Views and even a
Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
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21001: Contemporary Gem with a Private Pool & Great Outdoor Living Space! One Do
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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New Listing! New rear yard patio, central A/C, Free Wifi, family friendly
Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
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Walk To Joshua Pond and Main Street. Renovated 2BR Cottage. Mid-Cape.
Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 5
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Ideal Osterville Family Vacation Home w/AC, KIng Beds and Ocean/ Pond Beach Pass
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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236B Smoke Valley Road 153791
Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
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Walk To Joshua Pond & Main St. 2 Bedroom Cottage, Central Cape Location
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
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Unbeatable location, views and water access from this rare family compound
Rental Home
8 bedrooms
8 bathrooms
Sleeps 8
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Traditional Osterville Cape on Golf Course Near Beach/Village
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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Exclusive Little Neck Island Cape Cod House
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Osterville Retreat -Beach Pass
Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
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Two Bedrooms Near Osterville Center - Beach Pass Included - Air Conditioning
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
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Oyster Villa - Baby Friendly with Beach Pass
Rental Home
1 bedroom
1 bathroom
Sleeps 3
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Beautiful designed, newly constructed home- all the amenities, close to beaches
Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
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Charming Carriage House on Private Oceanfront Estate
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Overlooking Nantucket Sound, Classic Victorian Era home
Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
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Renovated Osterville Gem-Central Air + Beach Pass
Rental Home
3 bedrooms
1 bathroom
Sleeps 8
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Osterville Charmer, Walk to Beach
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Sea View Ave Brand New Construction - Pool Hot tub Tennis Court
Rental Home
4 bedrooms
6 bathrooms
Sleeps 10
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New listing: Quaint Osterville Cottage on 1+ acre
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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NEW! Updated Osterville Home: Beach Pass Provided!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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Walk to Joshua Pond Osterville! Sleeps 8, Pet friendly, Central AC
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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Dog Friendly - Close to Village & Beach
Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
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Sun Filled Modern Waterfront luxury rental home.
Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
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Adorable Pond Front Home Walking Distance to Town
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Stroll to Village or Beach
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Heated Pool in Osterville Close to Beaches and Attractions
Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
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In the Heart of Osterville Village Newly renovated Pets considered
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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Prime Osterville Location - Clean and Comfortable Family Home
Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
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Osterville Village newly renovated one mile to beach
Rental Home
6 bedrooms
7 bathrooms
Sleeps 8
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Brand New Osterville Home! Central AC, Walk/Bike to town or beach, Sleeps 10
Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
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Waterfront 4 beds in Oyster Harbors
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Osterville~Newly Renovated 3BR,2.5BA w/AC near Joshua Pond
Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
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Beautifully Renovated Townhome Steps from Osterville Village
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
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Spacious Osterville Cape Getaway, Close to Beaches and Village. Pass Included
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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Osterville Gem with Central A/C and Walking Distance to Joshua’s Pond!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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An Osterville Gem!!Very close to town and beach! Hot Tub & Beach Pass Included!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
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Showing results 1-50 of 62
Frequently Asked Questions about Osterville
- Yes, here are some popular vacation rentals in Osterville that have a pool:
- 236B Smoke Valley Road 153791
- Ideal Osterville Family Vacation Home w/AC, KIng Beds and Ocean/ Pond Beach Pass
- 271 Westwind Cir
- Yes, here are some popular vacation rentals in Osterville that have internet access:
- Ideal Osterville Family Vacation Home w/AC, KIng Beds and Ocean/ Pond Beach Pass
- 271 Westwind Cir
- In the Heart of Osterville Village Newly renovated Pets considered
- Some of the most popular kid friendly rentals in Osterville are:
- Ideal Osterville Family Vacation Home w/AC, KIng Beds and Ocean/ Pond Beach Pass
- 271 Westwind Cir
- In the Heart of Osterville Village Newly renovated Pets considered