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Osterville
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Osterville, MA Holiday Rentals & Apartments
Holiday Rentals
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Massachusetts (MA)
Cape Cod
Osterville, MA Holiday Rentals & Apartments
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Internet or Wifi (76)
Air Conditioning (76)
Grill (64)
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Kid friendly (72)
Pet friendly (25)
Elder access (2)
Smoking allowed (1)
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Holiday Rental House (74)
Condominium/Apartment (2)
Cabin Holiday Rental (0)
Private Room (0)
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Waterfront (7)
Boat Available (1)
Housekeeping Included (1)
Private Chef (0)
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Distance from
5 km
Osterville Village Library
Osterville Historical Society Museum
Skunknett River Wildife Sanctuary
A. Stanley Wheelock Antiques
Armstrong-Kelley Park
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76 rentals
in Osterville.
Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
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Beautiful Osterville Home central to everything!
4 reviews
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 8
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Osterville~Newly Renovated with central AC and beach pass
Holiday Rental House
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3 bedrooms
4 bathrooms
Sleeps 8
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Pristine Osterville Cottage
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
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Charming Cottage Getaway
43 reviews
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 3
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Osterville Charmer in a private neighborhood setting
5 reviews
Holiday Rental House
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1 bedroom
2 bathrooms
Sleeps 3
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Charming cottage steps to Osterville village. Near Dowses beach.
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Peaceful Cottage in the Heart of Osterville Village Walk to Shops & Restaurants
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 6
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Prime Osterville Location - Clean and Comfortable Family Home
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 8
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Walk To Joshua Pond & Main St. 2 Bedroom Cottage, Central Cape Location
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 6
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Your home away from home!
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
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Historic Home in Prime Osterville Village Location: Three bedrooms, Sleeps 6
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
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Charming Carriage House on Private Oceanfront Estate
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Cheerful 3 Bedroom Home in Osterville - Great Deck
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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OSTERVILLE VILLAGE NEWLY RENOVATED ON 6 ACRES CLOSE TO BEACHES
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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236B Smoke Valley Road 153791
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 5
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"Little Neck" Cottage just 3 minutes to Dowses Beach and downtown Osterville
2 reviews
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Great Outdoor Space Central AC WIFI Family Friendly
1 review
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 5
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Enchanting 2 Bedroom Cottage - 1 block to Village Center
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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Walk To Joshua Pond and Main Street. Renovated 2BR Cottage. Mid-Cape.
1 review
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 6
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Beautifully Renovated Cape Cottage with Pool!
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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Renovated Osterville Gem-Central Air + Beach Pass
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 8
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THREE BEDROOM CAPE NEAR PRIVATE SWIMMING POND
5 reviews
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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Osterville Village Home - Large Yard and Outdoor Entertaining Area
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 9
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Charming home in Osterville close to beach! Includes beach pass
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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Osterville - Spacious home 4 bedroom 3 bathroom in Wianno
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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Traditional Osterville Cape on Golf Course Near Beach/Village
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
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Perfectly Located Osterville Heights Rental
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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Spacious Osterville Cape Getaway, Close to Beaches and Village. Pass Included
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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Contemporary Gem with Private Pool!
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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271 Westwind Cir
2 reviews
Holiday Rental House
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3 bedrooms
4 bathrooms
Sleeps 6
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Quaint Osterville home with Swim Spa, on 1+ acre, close to Dowse's beach
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
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Osterville- Spacious, family friendly renovated 3BR, Outdoor shower & Beach Pass
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
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As seen on
Contemporary Gem with Private Pool!
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
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As seen on
Perfect Vacation Getaway!
1 review
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
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Antique elegance in Osterville
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
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As seen on
Perfectly Located Osterville Rental
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 8
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Sleeps
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Cozy Cape-style home in private neighborhood
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 10
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A wonderful place with A wonderful beach to spend a vacation !!
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 4
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Walk to Joshua Pond Beach & Downtown!
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
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Walk to Joshua Pond Osterville! Sleeps 8, Pet friendly, Central AC
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
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Osterville Gem with Central A/C and Walking Distance to Joshua’s Pond!
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 8
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Osterville Gem - close to Beach / Town
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 9
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As seen on
Walk to Joshua Pond Beach & Downtown!
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
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Cape escape with patio, grill, firepit, outdoor dining, fireplace & W/D
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
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Well-Located in Osterville Close to beach and village
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
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Spacious Cottage with English-Style Garden in Osterville Village, Cape Cod
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 7
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Walk to village and beach
Holiday Rental House
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5 bedrooms
4 bathrooms
Sleeps 10
Match:
Sleeps
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Charming Osterville Home with Pool
Holiday Rental House
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3 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Historic Home in Downtown Osterville with Beach Pass
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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Showing results 1-50 of 76
Frequently Asked Questions about Osterville
Do any holiday rentals in Osterville have a pool?
Yes, here are some popular holiday rentals in Osterville that have a pool:
236B Smoke Valley Road 153791
Contemporary Gem with Private Pool!
Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower
See all holiday rentals with a pool in Osterville on Tripadvisor
Do any holiday rentals in Osterville have internet access?
Yes, here are some popular holiday rentals in Osterville that have internet access:
Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower
Beautiful Osterville Home central to everything!
Osterville~Newly Renovated with central AC and beach pass
See all holiday rentals in Osterville on Tripadvisor
What are the best pet friendly rentals in Osterville?
The best pet friendly rentals in Osterville are:
Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower
Beautiful Osterville Home central to everything!
Pristine Osterville Cottage
See all pet friendly holiday rentals in Osterville on Tripadvisor
What are some great rentals in Osterville that are kid friendly?
Some of the most popular kid friendly rentals in Osterville are:
Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower
Beautiful Osterville Home central to everything!
Osterville~Newly Renovated with central AC and beach pass
See all kid friendly holiday rentals in Osterville on Tripadvisor