Osterville Vacation Rentals
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5 mi
63 rentals in Osterville.
Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower
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Close to beautiful Dowses beach, central AC, and pet friendly!
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Charming cottage steps to Osterville village. Near Dowses beach. RPMS094
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Prime Osterville Location - Clean and Comfortable Family Home
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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The Cape Escape Summa
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cheerful 3 Bedroom Home in Osterville - Great Deck
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In town Osterville village location
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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THREE BEDROOM CAPE NEAR PRIVATE SWIMMING POND
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Osterville- Spacious, family friendly renovated 3BR, Outdoor shower & Beach Pass
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Contemporary Gem with Private Pool!
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Cozy Cape-style home in private neighborhood
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A wonderful place with A wonderful beach to spend a vacation !!
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Walk to Joshua Pond Beach & Downtown!
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Walk to Joshua Pond Osterville! Sleeps 8, Pet friendly, Central AC
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Osterville village newly renovated 3 +bed 6 acres
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Heated Private Pool, Walk to beach & shops, fully renovated house
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WOW! Osterville MA, Enjoy & Relax! Beach Pass, Fire Pit, ⚓️Sleeps10!
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New Luxury Renovation in Prime Osterville Village: Five Bedrooms, Sleeps 10
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Osterville Cape Cod-Style Home - One Block from North Bay!
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Historic Home in Prime Osterville Village Location: Three bedrooms, Sleeps 6
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Lovely Osterville Home With New Gunite Pool and Beach Pass.
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Peaceful Cottage in the Heart of Osterville Village Walk to Shops & Restaurants
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Unbeatable location, views and water access from this rare family compound
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"The Half Shell" Cottage in Osterville Village
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Amazing updated waterfront home located in Osterville with a private dock
Rental Home
1 bedroom
1 bathroom
Sleeps 12
Match: Sleeps
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The Ultimate Cape Cod luxury home. Dock, pool, hot tub and views! RPMS104
Rental Home
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Enchanting 2 Bedroom Cottage - 1 block to Village Center
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Large home in the heart of Osterville Village, sleeps 11
Rental Home
6 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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3 bedroom Osterville home, Beach Pass Included
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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Swing Set, Plunge pool, and large yard await!
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Renovated & Comfortable Osterville Home - Close to Bakery
Rental Home
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Quaint Osterville home with Swim Spa
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Expansive Cape Cod Family Retreat
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Osterville Gem with Central A/C and Walking Distance to Joshua’s Pond!
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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
Match: Sleeps
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Traditional Cape on Wianno CC Golf Course Near Beach/Village with Beach Pass
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Updated with Pool in Charming Osterville Village: 032-Ov
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Cape escape with patio, grill, firepit, outdoor dining, W/D
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful designed, newly constructed home- all the amenities, close to beaches
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Great Outdoor Space Central AC WIFI Family Friendly
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Adorable 2 bedroom, 2 bath Osterville Cottage walk to Village, close to beach
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Private Nantucket style home with heated pool and beach pass
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Beautiful 3 bedroom, 3.5 bath house, walk to Osterville Village
Rental Home
4 bedrooms
5 bathrooms
Sleeps 7
Match: Sleeps
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Impressive Osterville Residence - Ideal Location
Rental Home
6 bedrooms
6 bathrooms
Sleeps 15
Match: Sleeps
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Osterville Village - New Pool Large Yard + Outdoor Entertaining Area
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Perfect Vacation Getaway!
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming Cottage Getaway
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Wonderful Osterville home close to Joshuas pond ~New to VRBO~
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Perfectly Located Osterville Heights Rental RPAM021
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Charming Carriage House on Private Oceanfront Estate
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Showing results 1-50 of 63
Frequently Asked Questions about Osterville
- Yes, here are some popular vacation rentals in Osterville that have a pool:
- Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower
- Close to beautiful Dowses beach, central AC, and pet friendly!
- Charming cottage steps to Osterville village. Near Dowses beach.
- Yes, here are some popular vacation rentals in Osterville that have internet access:
- Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower
- Close to beautiful Dowses beach, central AC, and pet friendly!
- Charming cottage steps to Osterville village. Near Dowses beach.
- Some of the most popular kid friendly rentals in Osterville are:
- Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower
- Close to beautiful Dowses beach, central AC, and pet friendly!
- Charming cottage steps to Osterville village. Near Dowses beach.
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