Osterville Vacation Rentals
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5 km
59 rentals in Osterville.
Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower
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Beautiful Osterville Home central to everything!
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Osterville~Newly Renovated with central AC and beach pass
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Pristine Osterville Cottage
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Close to beautiful Dowses beach, central AC, and pet friendly!
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Charming Cottage Getaway
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Charming cottage steps to Osterville village. Near Dowses beach. RPMS094
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Peaceful Cottage in the Heart of Osterville Village Walk to Shops & Restaurants
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Historic Home in Prime Osterville Village Location: Three bedrooms, Sleeps 6
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Cheerful 3 Bedroom Home in Osterville - Great Deck
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Great Outdoor Space Central AC WIFI Family Friendly
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Beautifully Renovated Cape Cottage with Pool!
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THREE BEDROOM CAPE NEAR PRIVATE SWIMMING POND
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Osterville Village - New Pool Large Yard + Outdoor Entertaining Area
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Traditional Cape on Wianno CC Golf Course Near Beach/Village with Beach Pass
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Perfectly Located Osterville Heights Rental RPAM021
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Spacious Osterville home, short commute from Boston,
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Quaint Osterville home with Swim Spa
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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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Walk to Joshua Pond Osterville! Sleeps 8, Pet friendly, Central AC
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Osterville Gem with Central A/C and Walking Distance to Joshua’s Pond!
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Cape escape with patio, grill, firepit, outdoor dining, W/D
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Walk to village and beach
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Charming Osterville Home with Pool
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4 Bed Osterville Home with Yard
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In the Heart of Osterville Village Newly renovated Pets considered RPMS087
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Seasons by the Sea: Fully Renovated Luxury Cape Cod Home
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Heated Private Pool, Walk to beach & shops, fully renovated house
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Brand New Osterville Home! Central AC, Walk/Bike to town or beach, Sleeps 10
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Overlooking Nantucket Sound, Classic Victorian Era home
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Private Nantucket style home with heated pool and beach pass
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Large waterfront home with deep water dock, you'll Fall in love with Breezy
Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Sea View Ave Brand New Construction - Pool Hot tub Tennis Court
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Beautiful designed, newly constructed home- all the amenities, close to beaches
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WOW! Osterville MA, Enjoy & Relax! Beach Pass, Fire Pit, Sleeps10!
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Waterfront/golf Sleep 8 /public beach Pass & private beach
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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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Impressive Osterville Residence - Ideal Location
Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 15
Match: Sleeps
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Unbeatable location, views and water access from this rare family compound
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Cape…on the Cape! Cute home near beach and center of town. Beach pass included.
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Perfect Vacation Getaway!
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Wonderful Osterville home close to Joshuas pond ~New to VRBO~
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Amazing updated waterfront home located in Osterville with a private dock
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 12
Match: Sleeps
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Brand new for 2025 6 bedroom with pool Close to village and beach. RPMS157
Holiday Rental House
6 bedrooms
8 bathrooms
Sleeps 12
Match: Sleeps
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"The Half Shell" Cottage in Osterville Village
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Expansive Cape Cod Family Retreat
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Large home in the heart of Osterville Village, sleeps 11
Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Showing results 1-50 of 59
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
- Beautiful Osterville Home central to everything!
- Osterville~Newly Renovated with central AC and beach pass
- Yes, here are some popular vacation 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
- 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
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