Osterville Holiday Apartments
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68 rentals in Osterville.
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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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Historic Home in Downtown Osterville with Beach Pass
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Cape Cod Private Oasis
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 13
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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
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Cape Cod Family Retreat
Holiday Rental House
12 bedrooms
8 bathrooms
Sleeps 24
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'The Half Shell' Cottage in Osterville Village
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
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Osterville Charmer in a private neighborhood setting
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 3
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RELAX AND ENJOY FUN in Osterville, MA ⚓️- Sleeps 10 - Beach Pass and more!
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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271 Westwind Cir
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
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OSTERVILLE, NORTH BAY WITH PRIVATE BEACH AND DOCK
Holiday Rental House
5 bedrooms
7 bathrooms
Sleeps 6
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
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Perfectly Located Osterville Heights Rental
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Walk To Joshua Pond & Main St. 2 Bedroom Cottage, Central Cape Location
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
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Perfectly Located Osterville Rental
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Off Season Discounts
Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 8
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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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Ideal Osterville Family Vacation Home w/AC, KIng Beds and Ocean/ Pond Beach Pass
Holiday Rental House
4 bedrooms
2 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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Exclusive Little Neck Island Cape Cod House
Holiday Rental House
4 bedrooms
3 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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Be the first to review our Rustic Cape Cod Barn!
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
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Oyster Villa - Baby Friendly with Beach Pass
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
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Beautiful Newly Constructed Home With All The Amenities And close to Beaches
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
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Charming Carriage House on Private Oceanfront Estate
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Overlooking Nantucket Sound, Classic Victorian Era home
Holiday Rental House
5 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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21001: Contemporary Gem with Private Pool & Great Outdoor Living Space!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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New listing: Quaint Osterville Cottage on 1+ acre
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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NEW! Updated Osterville Home: Beach Pass Provided!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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 Osterville! Sleeps 8, Pet friendly, Central A/C,
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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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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Dog Friendly - Close to Village & Beach
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
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Sun Filled Modern Waterfront
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
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Waterfront Home on Sam's Pond Close to Town and Beaches
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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Adorable Pond Front Home Walking Distance to Town
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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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
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In the Heart of Osterville Village Newly renovated Pets considered
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
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Osterville- Spacious, family friendly renovated 3BR, Outdoor shower & Beach Pass
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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Prime Osterville Location - Clean and Comfortable Family Home
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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Osterville Village newly renovated one mile to beach
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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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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Waterfront 4 beds in Oyster Harbors
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 2
Match: Sleeps
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Antique elegance in Osterville
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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