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Osterville Holiday Apartments

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68 rentals in Osterville.
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Charming Cottage Getaway, holiday rental in Osterville
Charming Cottage Getaway, holiday rental in Osterville
Charming Cottage Getaway, holiday rental 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 in Osterville
Beautiful Osterville Home central to everything!, holiday rental in Osterville
Beautiful Osterville Home central to everything!, holiday rental in Osterville

Beautiful Osterville Home central to everything!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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*Heated Priv. Pool, Walk to beach & shops, Fully Renovated house, holiday rental in Osterville
*Heated Priv. Pool, Walk to beach & shops, Fully Renovated house, holiday rental in Osterville
*Heated Priv. Pool, Walk to beach & shops, Fully Renovated house, holiday rental in Osterville

*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 in Osterville
Historic Home in Downtown Osterville with Beach Pass, holiday rental in Osterville
Historic Home in Downtown Osterville with Beach Pass, holiday rental in Osterville

Historic Home in Downtown Osterville with Beach Pass

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Cape Cod Private Oasis, holiday rental in Osterville
Cape Cod Private Oasis, holiday rental in Osterville
Cape Cod Private Oasis, holiday rental in Osterville

Cape Cod Private Oasis

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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Osterville Cape Cod-Style Home - One Block from North Bay!, holiday rental in Osterville
Osterville Cape Cod-Style Home - One Block from North Bay!, holiday rental in Osterville
Osterville Cape Cod-Style Home - One Block from North Bay!, holiday rental in Osterville

Osterville Cape Cod-Style Home - One Block from North Bay!

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Lovely Osterville Home With New Gunite Pool and Beach Pass., holiday rental in Osterville
Lovely Osterville Home With New Gunite Pool and Beach Pass., holiday rental in Osterville
Lovely Osterville Home With New Gunite Pool and Beach Pass., holiday rental in Osterville

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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Cape Cod Family Retreat, holiday rental in Osterville
Cape Cod Family Retreat, holiday rental in Osterville
Cape Cod Family Retreat, holiday rental in Osterville

Cape Cod Family Retreat

Holiday Rental House
12 bedrooms
8 bathrooms
Sleeps 24
Match: Sleeps
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'The Half Shell' Cottage in Osterville Village, holiday rental in Osterville
'The Half Shell' Cottage in Osterville Village, holiday rental in Osterville
'The Half Shell' Cottage in Osterville Village, holiday rental in Osterville

'The Half Shell' Cottage in Osterville Village

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Osterville Charmer in a private neighborhood setting, holiday rental in Osterville
Osterville Charmer in a private neighborhood setting, holiday rental in Osterville
Osterville Charmer in a private neighborhood setting, holiday rental in Osterville

Osterville Charmer in a private neighborhood setting

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
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RELAX AND ENJOY FUN in Osterville, MA ⚓️- Sleeps 10 - Beach Pass and more!, holiday rental in Osterville
RELAX AND ENJOY FUN in Osterville, MA ⚓️- Sleeps 10 - Beach Pass and more!, holiday rental in Osterville
RELAX AND ENJOY FUN in Osterville, MA ⚓️- Sleeps 10 - Beach Pass and more!, holiday rental in Osterville

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 in Osterville
271 Westwind Cir, holiday rental in Osterville
271 Westwind Cir, holiday rental in Osterville

271 Westwind Cir

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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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 in Osterville
Private Nantucket style home with heated pool and beach pass, holiday rental in Osterville
Private Nantucket style home with heated pool and beach pass, holiday rental in Osterville

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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Perfectly Located Osterville Heights Rental, holiday rental in Osterville
Perfectly Located Osterville Heights Rental, holiday rental in Osterville
Perfectly Located Osterville Heights Rental, holiday rental in Osterville

Perfectly Located Osterville Heights Rental

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Walk To Joshua Pond & Main St. 2 Bedroom Cottage, Central Cape Location, holiday rental in Osterville
Walk To Joshua Pond & Main St. 2 Bedroom Cottage, Central Cape Location, holiday rental in Osterville
Walk To Joshua Pond & Main St. 2 Bedroom Cottage, Central Cape Location, holiday rental in Osterville

Walk To Joshua Pond & Main St. 2 Bedroom Cottage, Central Cape Location

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Perfectly Located Osterville Rental, holiday rental in Osterville
Perfectly Located Osterville Rental, holiday rental in Osterville
Perfectly Located Osterville Rental, holiday rental in Osterville

Perfectly Located Osterville Rental

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Off Season Discounts, holiday rental in Osterville
Off Season Discounts, holiday rental in Osterville
Off Season Discounts, holiday rental in Osterville

Off Season Discounts

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Waterfront/golf Sleep 8 /public beach Pass & private beach, holiday rental in Osterville
Waterfront/golf Sleep 8 /public beach Pass & private beach, holiday rental in Osterville
Waterfront/golf Sleep 8 /public beach Pass & private beach, holiday rental in Osterville

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 in Osterville
Ideal Osterville Family Vacation Home w/AC, KIng Beds and Ocean/ Pond Beach Pass, holiday rental in Osterville
Ideal Osterville Family Vacation Home w/AC, KIng Beds and Ocean/ Pond Beach Pass, holiday rental in Osterville

Ideal Osterville Family Vacation Home w/AC, KIng Beds and Ocean/ Pond Beach Pass

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Unbeatable location, views and water access from this rare family compound, holiday rental in Osterville
Unbeatable location, views and water access from this rare family compound, holiday rental in Osterville
Unbeatable location, views and water access from this rare family compound, holiday rental in Osterville

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 in Osterville
Exclusive Little Neck Island Cape Cod House, holiday rental in Osterville
Exclusive Little Neck Island Cape Cod House, holiday rental in Osterville

Exclusive Little Neck Island Cape Cod House

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Two Bedrooms Near Osterville Center - Beach Pass Included - Air Conditioning, holiday rental in Osterville
Two Bedrooms Near Osterville Center - Beach Pass Included - Air Conditioning, holiday rental in Osterville
Two Bedrooms Near Osterville Center - Beach Pass Included - Air Conditioning, holiday rental in Osterville

Two Bedrooms Near Osterville Center - Beach Pass Included - Air Conditioning

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Be the first to review our Rustic Cape Cod Barn!, holiday rental in Osterville
Be the first to review our Rustic Cape Cod Barn!, holiday rental in Osterville
Be the first to review our Rustic Cape Cod Barn!, holiday rental in Osterville

Be the first to review our Rustic Cape Cod Barn!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Oyster Villa - Baby Friendly with Beach Pass, holiday rental in Osterville
Oyster Villa - Baby Friendly with Beach Pass, holiday rental in Osterville
Oyster Villa - Baby Friendly with Beach Pass, holiday rental in Osterville

Oyster Villa - Baby Friendly with Beach Pass

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Beautiful Newly Constructed Home With All The Amenities And close to Beaches, holiday rental in Osterville
Beautiful Newly Constructed Home With All The Amenities And close to Beaches, holiday rental in Osterville
Beautiful Newly Constructed Home With All The Amenities And close to Beaches, holiday rental in Osterville

Beautiful Newly Constructed Home With All The Amenities And 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 in Osterville
Charming Carriage House on Private Oceanfront Estate, holiday rental in Osterville
Charming Carriage House on Private Oceanfront Estate, holiday rental in Osterville

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 in Osterville
Overlooking Nantucket Sound, Classic Victorian Era home, holiday rental in Osterville
Overlooking Nantucket Sound, Classic Victorian Era home, holiday rental in Osterville

Overlooking Nantucket Sound, Classic Victorian Era home

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Osterville Gem - close to Beach / Town, holiday rental in Osterville
Osterville Gem - close to Beach / Town, holiday rental in Osterville
Osterville Gem - close to Beach / Town, holiday rental in Osterville

Osterville Gem - close to Beach / Town

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Beautifully Renovated Cape Cottage with Pool!, holiday rental in Osterville
Beautifully Renovated Cape Cottage with Pool!, holiday rental in Osterville
Beautifully Renovated Cape Cottage with Pool!, holiday rental in Osterville

Beautifully Renovated Cape Cottage with Pool!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Sea View Ave Brand New Construction - Pool Hot tub Tennis Court, holiday rental in Osterville
Sea View Ave Brand New Construction - Pool Hot tub Tennis Court, holiday rental in Osterville
Sea View Ave Brand New Construction - Pool Hot tub Tennis Court, holiday rental in Osterville

Sea View Ave Brand New Construction - Pool Hot tub Tennis Court

Holiday Rental House
4 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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21001: Contemporary Gem with Private Pool & Great Outdoor Living Space!, holiday rental in Osterville
21001: Contemporary Gem with Private Pool & Great Outdoor Living Space!, holiday rental in Osterville
21001: Contemporary Gem with Private Pool & Great Outdoor Living Space!, holiday rental in Osterville

21001: Contemporary Gem with Private Pool & Great Outdoor Living Space!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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New listing: Quaint Osterville Cottage on 1+ acre, holiday rental in Osterville
New listing: Quaint Osterville Cottage on 1+ acre, holiday rental in Osterville
New listing: Quaint Osterville Cottage on 1+ acre, holiday rental in Osterville

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 in Osterville
NEW! Updated Osterville Home: Beach Pass Provided!, holiday rental in Osterville
NEW! Updated Osterville Home: Beach Pass Provided!, holiday rental in Osterville

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 in Osterville
New Listing! New rear yard patio, central A/C, Free Wifi, family friendly, holiday rental in Osterville
New Listing! New rear yard patio, central A/C, Free Wifi, family friendly, holiday rental in Osterville

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 in Osterville
Walk to Joshua Pond Osterville! Sleeps 8, Pet friendly, Central A/C,, holiday rental in Osterville
Walk to Joshua Pond Osterville! Sleeps 8, Pet friendly, Central A/C,, holiday rental in Osterville

Walk to Joshua Pond Osterville! Sleeps 8, Pet friendly, Central A/C,

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Walk To Joshua Pond and Main Street. Renovated 2BR Cottage. Mid-Cape., holiday rental in Osterville
Walk To Joshua Pond and Main Street. Renovated 2BR Cottage. Mid-Cape., holiday rental in Osterville
Walk To Joshua Pond and Main Street. Renovated 2BR Cottage. Mid-Cape., holiday rental in Osterville

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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Dog Friendly - Close to Village & Beach, holiday rental in Osterville
Dog Friendly - Close to Village & Beach, holiday rental in Osterville
Dog Friendly - Close to Village & Beach, holiday rental in Osterville

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, holiday rental in Osterville
Sun Filled Modern Waterfront, holiday rental in Osterville
Sun Filled Modern Waterfront, holiday rental in Osterville

Sun Filled Modern Waterfront

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Home on Sam's Pond Close to Town and Beaches, holiday rental in Osterville
Waterfront Home on Sam's Pond Close to Town and Beaches, holiday rental in Osterville
Waterfront Home on Sam's Pond Close to Town and Beaches, holiday rental in Osterville

Waterfront Home on Sam's Pond Close to Town and Beaches

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Adorable Pond Front Home Walking Distance to Town, holiday rental in Osterville
Adorable Pond Front Home Walking Distance to Town, holiday rental in Osterville
Adorable Pond Front Home Walking Distance to Town, holiday rental in Osterville

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 in Osterville
Stroll to Village or Beach, holiday rental in Osterville
Stroll to Village or Beach, holiday rental in Osterville

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 in Osterville
Heated Pool in Osterville Close to Beaches and Attractions, holiday rental in Osterville
Heated Pool in Osterville Close to Beaches and Attractions, holiday rental in Osterville

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 in Osterville
In the Heart of Osterville Village  Newly renovated  Pets considered, holiday rental in Osterville
In the Heart of Osterville Village  Newly renovated  Pets considered, holiday rental in Osterville

In the Heart of Osterville Village Newly renovated Pets considered

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Osterville- Spacious, family friendly renovated 3BR, Outdoor shower & Beach Pass, holiday rental in Osterville
Osterville- Spacious, family friendly renovated 3BR, Outdoor shower & Beach Pass, holiday rental in Osterville
Osterville- Spacious, family friendly renovated 3BR, Outdoor shower & Beach Pass, holiday rental in Osterville

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 in Osterville
Prime Osterville Location - Clean and Comfortable Family Home, holiday rental in Osterville
Prime Osterville Location - Clean and Comfortable Family Home, holiday rental in Osterville

Prime Osterville Location - Clean and Comfortable Family Home

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Osterville Village newly renovated one mile to beach, holiday rental in Osterville
Osterville Village newly renovated one mile to beach, holiday rental in Osterville
Osterville Village newly renovated one mile to beach, holiday rental in Osterville

Osterville Village newly renovated one mile to beach

Holiday Rental House
4 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 in Osterville
Brand New Osterville Home! Central AC, Walk/Bike to town or beach, Sleeps 10, holiday rental in Osterville
Brand New Osterville Home! Central AC, Walk/Bike to town or beach, Sleeps 10, holiday rental in Osterville

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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Waterfront 4 beds in Oyster Harbors, holiday rental in Osterville
Waterfront 4 beds in Oyster Harbors, holiday rental in Osterville
Waterfront 4 beds in Oyster Harbors, holiday rental in Osterville

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 in Osterville
Antique elegance in Osterville, holiday rental in Osterville
Antique elegance in Osterville, holiday rental in Osterville

Antique elegance in Osterville

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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