Holiday Rentals in Osterville
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Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
Distance from
5 km
93 rentals in Osterville.
Charming Cottage Getaway
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Beautiful Osterville Home central to everything!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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*Heated Priv. Pool, Walk to beach & shops, Fully Renovated house
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Osterville Cape Cod-Style Home - One Block from North Bay!
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
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Lovely Osterville Home With New Gunite Pool and Beach Pass.
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Private Nantucket style home with heated pool and beach pass
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Enjoy & Relax! Beach Pass, Fire Pit, Osterville, MA! Cape Cod⚓️- Sleeps 10!
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Osterville Charmer in a private neighborhood setting
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
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THREE BEDROOM CAPE NEAR PRIVATE SWIMMING POND
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Off Season Discounts
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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271 Westwind Cir
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
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"Little Neck" Cottage just 3 minutes to Dowses Beach and downtown Osterville
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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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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Perfect Vacation Getaway!
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Large waterfront home with deep water dock, you'll Fall in love with Breezy
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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New Listing! New rear yard patio, central A/C, Free Wifi, family friendly
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Walk To Joshua Pond and Main Street. Renovated 2BR Cottage. Mid-Cape.
Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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OSTERVILLE VILLAGE NEWLY RENOVATED ON 6 ACRES CLOSE TO BEACHES
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Unbeatable location, views and water access from this rare family compound
Holiday Rental House
8 bedrooms
8 bathrooms
Sleeps 20
Match: Sleeps
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Traditional Osterville Cape on Golf Course Near Beach/Village
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Exclusive Little Neck Island Cape Cod House
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Osterville Retreat -Beach Pass
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront/golf Sleep 8 /public beach Pass & private beach
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Spacious Cottage with English-Style Garden in Osterville Village, Cape Cod
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Historic Home in Downtown Osterville with Beach Pass
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful designed, newly constructed home- all the amenities, close to beaches
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Charming Carriage House on Private Oceanfront Estate
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Overlooking Nantucket Sound, Classic Victorian Era home
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
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Renovated Osterville Gem-Central Air + Beach Pass
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Spacious Tucked Away Home, 1.5m from Town
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 10
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Osterville Gem - close to Beach / Town
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 9
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Beautifully Renovated Cape Cottage with Pool!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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Sea View Ave Brand New Construction - Pool Hot tub Tennis Court
Holiday Rental House
4 bedrooms
6 bathrooms
Sleeps 10
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Quaint Osterville home with Swim Spa, on 1+ acre, close to Dowse's beach
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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Walk to Joshua Pond Osterville! Sleeps 8, Pet friendly, Central AC
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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Dog Friendly - Close to Village & Beach
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Sun Filled Modern Waterfront luxury rental home. Hot tub and fire pit.
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
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Adorable Pond Front Home Walking Distance to Town
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Stroll to Village or Beach
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Heated Pool in Osterville Close to Beaches and Attractions
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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In the Heart of Osterville Village Newly renovated Pets considered
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Osterville- Spacious, family friendly renovated 3BR, Outdoor shower & Beach Pass
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Prime Osterville Location - Clean and Comfortable Family Home
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Osterville Village newly renovated one mile to beach
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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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
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Antique elegance in Osterville
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Osterville~Newly Renovated with central AC and beach pass
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Beautifully Renovated Townhome Steps from Osterville Village
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Spacious Osterville Cape Getaway, Close to Beaches and Village. Pass Included
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Osterville Gem with Central A/C and Walking Distance to Joshua’s Pond!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Showing results 1-50 of 93
Frequently Asked Questions about Osterville
- Yes, here are some popular holiday rentals in Osterville that have a pool:
- Lovely Osterville Home With New Gunite Pool and Beach Pass.
- 236B Smoke Valley Road 153791
- 271 Westwind Cir
- Yes, here are some popular holiday rentals in Osterville that have internet access:
- 271 Westwind Cir
- In the Heart of Osterville Village Newly renovated Pets considered
- OSTERVILLE VILLAGE NEWLY RENOVATED ON 6 ACRES CLOSE TO BEACHES
- Some of the most popular kid friendly rentals in Osterville are:
- 271 Westwind Cir
- In the Heart of Osterville Village Newly renovated Pets considered
- OSTERVILLE VILLAGE NEWLY RENOVATED ON 6 ACRES CLOSE TO BEACHES