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Osterville Vacation Rentals

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Bathrooms

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5 mi
61 rentals in Osterville.
Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower, vacation rental in Osterville
Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower, vacation rental in Osterville
Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower, vacation rental in Osterville

Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Close to beautiful Dowses beach, central AC, and pet friendly!, vacation rental in Osterville
Close to beautiful Dowses beach, central AC, and pet friendly!, vacation rental in Osterville
Close to beautiful Dowses beach, central AC, and pet friendly!, vacation rental in Osterville

Close to beautiful Dowses beach, central AC, and pet friendly!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Charming cottage steps to Osterville village.  Near Dowses beach., vacation rental in Osterville
Charming cottage steps to Osterville village.  Near Dowses beach., vacation rental in Osterville
Charming cottage steps to Osterville village.  Near Dowses beach., vacation rental in Osterville

Charming cottage steps to Osterville village. Near Dowses beach.

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Prime Osterville Location - Clean and Comfortable Family Home, vacation rental in Osterville
Prime Osterville Location - Clean and Comfortable Family Home, vacation rental in Osterville
Prime Osterville Location - Clean and Comfortable Family Home, vacation rental in Osterville

Prime Osterville Location - Clean and Comfortable Family Home

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Cape Escape Summa, vacation rental in Osterville
The Cape Escape Summa, vacation rental in Osterville
The Cape Escape Summa, vacation rental in Osterville

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, vacation rental in Osterville
Cheerful 3 Bedroom Home in Osterville - Great Deck, vacation rental in Osterville
Cheerful 3 Bedroom Home in Osterville - Great Deck, vacation rental in Osterville

Cheerful 3 Bedroom Home in Osterville - Great Deck

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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In town Osterville village location, vacation rental in Osterville
In town Osterville village location, vacation rental in Osterville
In town Osterville village location, vacation rental in Osterville

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, vacation rental in Osterville
THREE BEDROOM CAPE NEAR PRIVATE SWIMMING POND, vacation rental in Osterville
THREE BEDROOM CAPE NEAR PRIVATE SWIMMING POND, vacation rental in Osterville

THREE BEDROOM CAPE NEAR PRIVATE SWIMMING POND

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Osterville- Spacious, family friendly renovated 3BR, Outdoor shower & Beach Pass, vacation rental in Osterville
Osterville- Spacious, family friendly renovated 3BR, Outdoor shower & Beach Pass, vacation rental in Osterville
Osterville- Spacious, family friendly renovated 3BR, Outdoor shower & Beach Pass, vacation rental in Osterville

Osterville- Spacious, family friendly renovated 3BR, Outdoor shower & Beach Pass

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Contemporary Gem with Private Pool!, vacation rental in Osterville
Contemporary Gem with Private Pool!, vacation rental in Osterville
Contemporary Gem with Private Pool!, vacation rental in Osterville

Contemporary Gem with Private Pool!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy Cape-style home in private neighborhood, vacation rental in Osterville
Cozy Cape-style home in private neighborhood, vacation rental in Osterville
Cozy Cape-style home in private neighborhood, vacation rental in Osterville

Cozy Cape-style home in private neighborhood

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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A wonderful place with A wonderful beach to spend a vacation !!, vacation rental in Osterville
A wonderful place with A wonderful beach to spend a vacation !!, vacation rental in Osterville
A wonderful place with A wonderful beach to spend a vacation !!, vacation rental in Osterville

A wonderful place with A wonderful beach to spend a vacation !!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Walk to Joshua Pond Beach & Downtown!, vacation rental in Osterville
Walk to Joshua Pond Beach & Downtown!, vacation rental in Osterville
Walk to Joshua Pond Beach & Downtown!, vacation rental in Osterville

Walk to Joshua Pond Beach & Downtown!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Walk to Joshua Pond Osterville! Sleeps 8, Pet friendly, Central AC, vacation rental in Osterville
Walk to Joshua Pond Osterville! Sleeps 8, Pet friendly, Central AC, vacation rental in Osterville
Walk to Joshua Pond Osterville! Sleeps 8, Pet friendly, Central AC, vacation rental in Osterville

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, vacation rental in Osterville
Osterville village newly renovated 3 +bed 6 acres, vacation rental in Osterville
Osterville village newly renovated 3 +bed 6 acres, vacation rental in Osterville

Osterville village newly renovated 3 +bed 6 acres

Rental Home
4 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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Heated Private Pool, Walk to beach & shops, fully renovated house, vacation rental in Osterville
Heated Private Pool, Walk to beach & shops, fully renovated house, vacation rental in Osterville
Heated Private Pool, Walk to beach & shops, fully renovated house, vacation rental in Osterville

Heated Private Pool, Walk to beach & shops, fully renovated house

Rental Home
4 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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WOW! Osterville MA, Enjoy & Relax! Beach Pass, Fire Pit, ⚓️Sleeps10!, vacation rental in Osterville
WOW! Osterville MA, Enjoy & Relax! Beach Pass, Fire Pit, ⚓️Sleeps10!, vacation rental in Osterville
WOW! Osterville MA, Enjoy & Relax! Beach Pass, Fire Pit, ⚓️Sleeps10!, vacation rental in Osterville

WOW! Osterville MA, Enjoy & Relax! Beach Pass, Fire Pit, ⚓️Sleeps10!

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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New Luxury Renovation in Prime Osterville Village: Five Bedrooms, Sleeps 10, vacation rental in Osterville
New Luxury Renovation in Prime Osterville Village: Five Bedrooms, Sleeps 10, vacation rental in Osterville
New Luxury Renovation in Prime Osterville Village: Five Bedrooms, Sleeps 10, vacation rental in Osterville

New Luxury Renovation in Prime Osterville Village: Five Bedrooms, Sleeps 10

Rental Home
4 bedrooms
6 bathrooms
Sleeps 9
Match: Sleeps
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Perfect Vacation Getaway!, vacation rental in Osterville
Perfect Vacation Getaway!, vacation rental in Osterville
Perfect Vacation Getaway!, vacation rental in Osterville

Perfect Vacation Getaway!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cape escape with patio, grill, firepit, outdoor dining, W/D, vacation rental in Osterville
Cape escape with patio, grill, firepit, outdoor dining, W/D, vacation rental in Osterville
Cape escape with patio, grill, firepit, outdoor dining, W/D, vacation rental in Osterville

Cape escape with patio, grill, firepit, outdoor dining, W/D

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Osterville Cape Cod-Style Home - One Block from North Bay!, vacation rental in Osterville
Osterville Cape Cod-Style Home - One Block from North Bay!, vacation rental in Osterville
Osterville Cape Cod-Style Home - One Block from North Bay!, vacation rental in Osterville

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

Rental Home
6 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Osterville Gem with Central A/C and Walking Distance to Joshua’s Pond!, vacation rental in Osterville
Osterville Gem with Central A/C and Walking Distance to Joshua’s Pond!, vacation rental in Osterville
Osterville Gem with Central A/C and Walking Distance to Joshua’s Pond!, vacation rental in Osterville

Osterville Gem with Central A/C and Walking Distance to Joshua’s Pond!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spacious Osterville home, short commute from Boston,, vacation rental in Osterville
Spacious Osterville home, short commute from Boston,, vacation rental in Osterville
Spacious Osterville home, short commute from Boston,, vacation rental in Osterville

Spacious Osterville home, short commute from Boston,

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lovely Osterville Home With New Gunite Pool and Beach Pass., vacation rental in Osterville
Lovely Osterville Home With New Gunite Pool and Beach Pass., vacation rental in Osterville
Lovely Osterville Home With New Gunite Pool and Beach Pass., vacation rental in Osterville

Lovely Osterville Home With New Gunite Pool and Beach Pass.

Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Beautiful Osterville Home w/Heated Pool, Sleeps 13. Bike to beach, vacation rental in Osterville
Beautiful Osterville Home w/Heated Pool, Sleeps 13. Bike to beach, vacation rental in Osterville
Beautiful Osterville Home w/Heated Pool, Sleeps 13. Bike to beach, vacation rental in Osterville

Beautiful Osterville Home w/Heated Pool, Sleeps 13. Bike to beach

Rental Home
5 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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3 bedroom Osterville home, Beach Pass Included, vacation rental in Osterville
3 bedroom Osterville home, Beach Pass Included, vacation rental in Osterville
3 bedroom Osterville home, Beach Pass Included, vacation rental in Osterville

3 bedroom Osterville home, Beach Pass Included

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming Cottage Getaway, vacation rental in Osterville
Charming Cottage Getaway, vacation rental in Osterville
Charming Cottage Getaway, vacation rental in Osterville

Charming Cottage Getaway

Rental Home
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Wonderful Osterville home close to Joshuas pond ~New to VRBO~, vacation rental in Osterville
Wonderful Osterville home close to Joshuas pond ~New to VRBO~, vacation rental in Osterville
Wonderful Osterville home close to Joshuas pond ~New to VRBO~, vacation rental in Osterville

Wonderful Osterville home close to Joshuas pond ~New to VRBO~

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Sea View Ave Brand New Construction - Pool Hot tub Tennis Court, vacation rental in Osterville
Sea View Ave Brand New Construction - Pool Hot tub Tennis Court, vacation rental in Osterville
Sea View Ave Brand New Construction - Pool Hot tub Tennis Court, vacation rental in Osterville

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

Rental Home
4 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Enchanting 2 Bedroom Cottage - 1 block to Village Center, vacation rental in Osterville
Enchanting 2 Bedroom Cottage - 1 block to Village Center, vacation rental in Osterville
Enchanting 2 Bedroom Cottage - 1 block to Village Center, vacation rental in Osterville

Enchanting 2 Bedroom Cottage - 1 block to Village Center

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Traditional Cape on Wianno CC Golf Course Near Beach/Village with Beach Pass, vacation rental in Osterville
Traditional Cape on Wianno CC Golf Course Near Beach/Village with Beach Pass, vacation rental in Osterville
Traditional Cape on Wianno CC Golf Course Near Beach/Village with Beach Pass, vacation rental in Osterville

Traditional Cape on Wianno CC Golf Course Near Beach/Village with Beach Pass

Rental Home
6 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful designed, newly constructed home- all the amenities, close to beaches, vacation rental in Osterville
Beautiful designed, newly constructed home- all the amenities, close to beaches, vacation rental in Osterville
Beautiful designed, newly constructed home- all the amenities, close to beaches, vacation rental in Osterville

Beautiful designed, newly constructed home- all the amenities, close to beaches

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Osterville~Newly Renovated with central AC and beach pass, vacation rental in Osterville
Osterville~Newly Renovated with central AC and beach pass, vacation rental in Osterville
Osterville~Newly Renovated with central AC and beach pass, vacation rental in Osterville

Osterville~Newly Renovated with central AC and beach pass

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Osterville Village - New Pool Large Yard + Outdoor Entertaining Area, vacation rental in Osterville
Osterville Village - New Pool Large Yard + Outdoor Entertaining Area, vacation rental in Osterville
Osterville Village - New Pool Large Yard + Outdoor Entertaining Area, vacation rental in Osterville

Osterville Village - New Pool Large Yard + Outdoor Entertaining Area

Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Adorable 2 bedroom, 2 bath Osterville Cottage walk to Village, close to beach, vacation rental in Osterville
Adorable 2 bedroom, 2 bath Osterville Cottage walk to Village, close to beach, vacation rental in Osterville
Adorable 2 bedroom, 2 bath Osterville Cottage walk to Village, close to beach, vacation rental in Osterville

Adorable 2 bedroom, 2 bath Osterville Cottage walk to Village, close to beach

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Peaceful Cottage in the Heart of Osterville Village Walk to Shops & Restaurants, vacation rental in Osterville
Peaceful Cottage in the Heart of Osterville Village Walk to Shops & Restaurants, vacation rental in Osterville
Peaceful Cottage in the Heart of Osterville Village Walk to Shops & Restaurants, vacation rental in Osterville

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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Amazing updated waterfront home located in Osterville with a private dock, vacation rental in Osterville
Amazing updated waterfront home located in Osterville with a private dock, vacation rental in Osterville
Amazing updated waterfront home located in Osterville with a private dock, vacation rental in Osterville

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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Unbeatable location, views and water access from this rare family compound, vacation rental in Osterville
Unbeatable location, views and water access from this rare family compound, vacation rental in Osterville
Unbeatable location, views and water access from this rare family compound, vacation rental in Osterville

Unbeatable location, views and water access from this rare family compound

Rental Home
8 bedrooms
8 bathrooms
Sleeps 20
Match: Sleeps
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Expansive Cape Cod Family Retreat, vacation rental in Osterville
Expansive Cape Cod Family Retreat, vacation rental in Osterville
Expansive Cape Cod Family Retreat, vacation rental in Osterville

Expansive Cape Cod Family Retreat

Rental Home
11 bedrooms
7 bathrooms
Sleeps 22
Match: Sleeps
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"The Half Shell" Cottage in Osterville Village, vacation rental in Osterville
"The Half Shell" Cottage in Osterville Village, vacation rental in Osterville
"The Half Shell" Cottage in Osterville Village, vacation rental in Osterville

"The Half Shell" Cottage in Osterville Village

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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In the Heart of Osterville Village  Newly renovated  Pets considered RPMS087, vacation rental in Osterville
In the Heart of Osterville Village  Newly renovated  Pets considered RPMS087, vacation rental in Osterville
In the Heart of Osterville Village  Newly renovated  Pets considered RPMS087, vacation rental in Osterville

In the Heart of Osterville Village Newly renovated Pets considered RPMS087

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Large waterfront home with deep water dock, you'll Fall in love with Breezy, vacation rental in Osterville
Large waterfront home with deep water dock, you'll Fall in love with Breezy, vacation rental in Osterville
Large waterfront home with deep water dock, you'll Fall in love with Breezy, vacation rental in Osterville

Large waterfront home with deep water dock, you'll Fall in love with Breezy

Rental Home
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Swing Set, Plunge pool, and large yard await!, vacation rental in Osterville
Swing Set, Plunge pool, and large yard await!, vacation rental in Osterville
Swing Set, Plunge pool, and large yard await!, vacation rental in Osterville

Swing Set, Plunge pool, and large yard await!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Updated with Pool in Charming Osterville Village: 032-Ov, vacation rental in Osterville
Updated with Pool in Charming Osterville Village: 032-Ov, vacation rental in Osterville
Updated with Pool in Charming Osterville Village: 032-Ov, vacation rental in Osterville

Updated with Pool in Charming Osterville Village: 032-Ov

Rental Home
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Beautifully Renovated Cape Cottage with Pool!, vacation rental in Osterville
Beautifully Renovated Cape Cottage with Pool!, vacation rental in Osterville
Beautifully Renovated Cape Cottage with Pool!, vacation rental in Osterville

Beautifully Renovated Cape Cottage with Pool!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful 3 bedroom, 3.5 bath house, walk to Osterville Village, vacation rental in Osterville
Beautiful 3 bedroom, 3.5 bath house, walk to Osterville Village, vacation rental in Osterville
Beautiful 3 bedroom, 3.5 bath house, walk to Osterville Village, vacation rental in Osterville

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, vacation rental in Osterville
Impressive Osterville Residence - Ideal Location, vacation rental in Osterville
Impressive Osterville Residence - Ideal Location, vacation rental in Osterville

Impressive Osterville Residence - Ideal Location

Rental Home
6 bedrooms
6 bathrooms
Sleeps 15
Match: Sleeps
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Great Outdoor Space Central AC WIFI Family Friendly, vacation rental in Osterville
Great Outdoor Space Central AC WIFI Family Friendly, vacation rental in Osterville
Great Outdoor Space Central AC WIFI Family Friendly, vacation rental in Osterville

Great Outdoor Space Central AC WIFI Family Friendly

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Pristine Osterville Cottage, vacation rental in Osterville
Pristine Osterville Cottage, vacation rental in Osterville
Pristine Osterville Cottage, vacation rental in Osterville

Pristine Osterville Cottage

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful Osterville Home central to everything!, vacation rental in Osterville
Beautiful Osterville Home central to everything!, vacation rental in Osterville
Beautiful Osterville Home central to everything!, vacation rental in Osterville

Beautiful Osterville Home central to everything!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Showing results 1-50 of 61
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