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Osterville Vacation Rentals & Homes - 49 Rentals Available

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1 / 25

Osterville Home
2 BR / 3 BA / Sleeps 6 2 6 7 night min stayHome / 2 Bedrooms / Sleeps 6
2 bedrooms 3 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
This brand new home is stunning! Just built with luxury touches and all on one level. Large open floor plan with comfortable living room that opens to the Gourmet kitchen, dining area and half bath. King master with en...

from

$571

/ night

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1 / 39

Osterville Home
5 BR / 5 BA / Sleeps 8 5 8 7 night min stayHome / 5 Bedrooms / Sleeps 8
5 bedrooms 5 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
This magnificent waterfront residence on Oyster Harbors has the feeling and look of a European estate. With a stucco exterior and extensive gardens, thehome has distinct features and is stunning. Completely remodeled in...

from

$2,143

/ night

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Osterville Massachusetts Vacation Rentals - Home
1 / 19

Osterville Home
3 BR / 2 BA / Sleeps 8 3 8 7 night min stayHome / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Exclusive Robert Paul Properties rental home. Great family home in Osterville. Located in desirable Hickory Hills, this handsome, wood- shingled Contemporary sits high upon a beautifully landscaped lot. This property o...

from

$429

/ night

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1 / 24

Osterville Home
6 BR / 4 BA / Sleeps 12 6 12 7 night min stayHome / 6 Bedrooms / Sleeps 12
6 bedrooms 4 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
Welcome to the "The Black Pearl", a vintage home located at one of the Cape's most coveted locations in Oyster Harbors! This charming cape home is in the prime location facing Sampson's Island, Cotuit Bay, and Martha...

from

$3,571

/ night

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1 / 42

Osterville Home
5 BR / 7 BA / Sleeps 15 5 15 7 night min stayHome / 5 Bedrooms / Sleeps 15
5 bedrooms 7 bathrooms Sleeps 15
High Speed Internet • Dishwasher • Microwave
In prestigious Oyster Harbors gated community. This family home has it all! Heated pool, large yard, game room with pool table and foze ball. There is a theater/media room and a wonderfully well- appointed kitchen as ...

from

$2,143

/ night

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1 / 14

Osterville Home
3 BR / 3 BA / Sleeps 6 3 6 7 night min stayHome / 3 Bedrooms / Sleeps 6
3 bedrooms 3 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Walk to the village from this lovely Three bedroom, three full bath home. There is central air for your comfort as well as a screened in deck for relaxing. This home is not far from Dowses beach and a beach pass is prov...

from

$429

/ night

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Osterville Massachusetts Vacation Rentals - Home
1 / 22

Osterville Home
4 BR / 4 BA / Sleeps 8 4 8 7 night min stayHome / 4 Bedrooms / Sleeps 8
4 bedrooms 4 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Robert Paul Properties rental home. 7 homes to Village Center! Wonderful Osterville home in "the Village" . Well appointed and comfortable. New custom 2nd floor master suite has been added spacious deck overlooking golf...

from

$714

/ night

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1 / 35

Osterville Home
4 BR / 4 BA / Sleeps 8 4 8 7 night min stayHome / 4 Bedrooms / Sleeps 8
4 bedrooms 4 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
This home has been totally renovated from top to bottom for the 2016 rental season. There are four bedrooms. A master suite on the first level and three bedrooms upstairs. Three full baths and TV room in lower level. Sun...

from

$757

/ night

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1 / 19

Osterville Home
4 BR / 4 BA / Sleeps 10 4 10 7 night min stayHome / 4 Bedrooms / Sleeps 10
4 bedrooms 4 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
Enjoy sunsets from this charming Cape Cod rental overlooking West Bay. A deeded path meanders down to the bay for easy access to the water. This 4- bedroom, 3. 5- bath home is perfectly located in the heart of Wianno an...

from

$643

/ night

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1 / 28

Osterville Home
6 BR / 5 BA / Sleeps 12 6 12 7 night min stayHome / 6 Bedrooms / Sleeps 12
6 bedrooms 5 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
Welcome to Osterville! Spacious newly renovated Luxury rental property in the gated community of Oyster Harbors with a heated pool, water view of West Bay and private dock. Drink your coffee on the terrace or take a sw...

from

$3,571

/ night

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Osterville Massachusetts Vacation Rentals - Home
1 / 24

Osterville Home
4 BR / 2 BA / Sleeps 8 4 8 7 night min stayHome / 4 Bedrooms / Sleeps 8
4 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Lovely four bedroom rental home in the heart of Osterville. Short walk to village and not far from Dowses Beach. Two bedrooms, living room, dining room and sitting area on the first level as well as a full bath. Second...

from

$357

/ night

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Osterville Massachusetts Vacation Rentals - Home
1 / 20

Osterville Home
5 BR / 3 BA / Sleeps 12 5 12 7 night min stayHome / 5 Bedrooms / Sleeps 12
5 bedrooms 3 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
Less than a mile to heart of downtown Osterville and 1. 5 miles to Dowses Beach this location is perfect! This lovely, light and bright home is filled with Cape Cod style! Providing plenty of space for family and frie...

from

$714

/ night

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Osterville Massachusetts Vacation Rentals - Home
1 / 16

Osterville Home
6 BR / 4 BA / Sleeps 10 6 10 7 night min stayHome / 6 Bedrooms / Sleeps 10
6 bedrooms 4 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
Great family home located between Dowes beach and Osterville village. There are six bedrooms and four full baths and central air for your comfort. The first level offers a large formal dining room, well equipped kitchen...

from

$643

/ night

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Osterville Massachusetts Vacation Rentals - Home
1 / 38

Osterville Home
9 BR / 9 BA / Sleeps 15 9 15 7 night min stayHome / 9 Bedrooms / Sleeps 15
9 bedrooms 9 bathrooms Sleeps 15
High Speed Internet • Dishwasher • Microwave
Quiet luxury on the water†™ s edge. Feel at one with the sand, surf, and sun while luxuriating on your own beach surrounded by a private and lush 26 acres in the exclusive gated paradise that is Oyster ...

from

$3,571

/ night

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Osterville Massachusetts Vacation Rentals - Home
1 / 41

Osterville Home
11 BR / 7 BA / Sleeps 12 11 12 7 night min stayHome / 11 Bedrooms / Sleeps 12
11 bedrooms 7 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
Large family home waterfront home on Sea View Ave in Osterville with 140' + /- of soft sandy beach on the shores of Nantucket Sound, this quintessential Osterville estate is set on 2. 23 acres of rolling green lawns, ...

from

$1,786

/ night

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Osterville Massachusetts Vacation Rentals - Home
1 / 19

Osterville Home
3 BR / 4 BA / Sleeps 8 3 8 7 night min stayHome / 3 Bedrooms / Sleeps 8
3 bedrooms 4 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Bright, lovely secluded home on almost 3 acres in prestigious Seapuit enclave of large estate homes. Main house has 3 BR (each w/private bath). Meticulously maintained, with beautiful landscaping, serenity, and priva...

from

$714

/ night

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1 / 12

Osterville Home
3 BR / 3 BA / Sleeps 5 3 5 7 night min stayHome / 3 Bedrooms / Sleeps 5
3 bedrooms 3 bathrooms Sleeps 5
High Speed Internet • Dishwasher • Microwave
This stunning waterfront home is a one of a kind with breathtaking views from every angle. There is a 40 pier (5. 5 draw) that†™ s ideal for boating and fishing. This three bedroom home is perfectly appoi...

from

$407

/ night

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Osterville Massachusetts Vacation Rentals - Home
1 / 27

Osterville Home
6 BR / 4 BA / Sleeps 8 6 8 7 night min stayHome / 6 Bedrooms / Sleeps 8
6 bedrooms 4 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Where else can you stroll to village, North Bay and Wianno Golf Course? There are six bedrooms and three full and one half baths. Lush landscaping to the mahogany deck with gazebo overlooking this private back yard to t...

from

$857

/ night

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Osterville Massachusetts Vacation Rentals - Home
1 / 15

Osterville Home
3 BR / 2 BA / Sleeps 8 3 8 7 night min stayHome / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Lovely three bedroom with bonus sleeping area in lower level. This Osterville home is close to Dowses Beach. Spacious and comfortable with a sun room and large backyard for family gatherings. Just minutes to the charming...

from

$500

/ night

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Osterville Massachusetts Vacation Rentals - Home
1 / 16

Osterville Home
4 BR / 2 BA / Sleeps 8 4 8 7 night min stayHome / 4 Bedrooms / Sleeps 8
4 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Close to Osterville Village and Joshua's Pond, this charming rental home has four bedrooms including a master suite with full bath on second level and 3 bedrooms and full bath on first floor. Living room and family room...

from

$257

/ night

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Osterville Massachusetts Vacation Rentals - Home
1 / 28

Osterville Home
12 BR / 8 BA / Sleeps 15 12 15 7 night min stayHome / 12 Bedrooms / Sleeps 15
12 bedrooms 8 bathrooms Sleeps 15
High Speed Internet • Dishwasher • Microwave
Cape Cod charm at its best and most elegant. An exquisite home for your family's ideal vacation. Private beach, tennis court. This grand house boasts 12 bedrooms, 7 full baths, 2 living rooms, a pool table, wrap aro...

from

$1,786

/ night

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Osterville Massachusetts Vacation Rentals - Home
1 / 13

Osterville Home
3 BR / 2 BA / Sleeps 8 3 8 7 night min stayHome / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Close to Main Street in Osterville and not far from Dowses Beach. Three bedrooms and a bonus sleeping area with bunk bed, couch and flat screen TV. Private deck, outdoor shower. Lovely setting in Osterville. Additional...

from

$457

/ night

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Osterville Massachusetts Vacation Rentals - Home
1 / 21

Osterville Home
2 BR / 2 BA / Sleeps 4 2 4 7 night min stayHome / 2 Bedrooms / Sleeps 4
2 bedrooms 2 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
Robert Paul Properties rental. Walk to the village from this two bedroom, two full bath first floor condo unit on Parker Road. Garage for use while renting and not far from Dowes beach. There are two screened porches an...

from

$286

/ night

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Osterville Massachusetts Vacation Rentals - Home
1 / 17

Osterville Home
3 BR / 4 BA / Sleeps 6 3 6 7 night min stayHome / 3 Bedrooms / Sleeps 6
3 bedrooms 4 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
BEAUTIFUL SEAPUIT HOME IN OSTERVILLE NEAR VILLAGEEXQUISITE home on almost three acres in Osterville s coveted "Seapuit" enclave (which fronts North Bay) ~ A gracious & comfortable gem with 3 bedrooms (sleeps six plus a l...

from

$414

/ night

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Osterville Massachusetts Vacation Rentals - Home
1 / 27

Osterville Home
3 BR / 3 BA / Sleeps 6 3 6 7 night min stayHome / 3 Bedrooms / Sleeps 6
3 bedrooms 3 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
South Of Rte. 28 ~ Osterville ! ! Beach Pass! Only July Week Remaining On Special ! Come Enjoy This Newly Remodeled Bright & Sunny Vacation Home On A Quiet Street In Lovely Osterville Woods! Quick Access To Beautiful...

from

$214

/ night

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Osterville Massachusetts Vacation Rentals - Home
1 / 21

Osterville Home
8 BR / 8 BA / Sleeps 20 8 20 7 night min stayHome / 8 Bedrooms / Sleeps 20
8 bedrooms 8 bathrooms Sleeps 20
High Speed Internet • Dishwasher • Microwave
Robert Paul Properties rental home. Cape Cod charm in every space. This Osterville private compound has lots of living areas and expansive water views from both main home and boathouse. This family Estate offers beach, ...

from

$2,357

/ night

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Osterville Massachusetts Vacation Rentals - Home
1 / 17

Osterville Home
4 BR / 3 BA / Sleeps 8 4 8 7 night min stayHome / 4 Bedrooms / Sleeps 8
4 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Osterville Villlage Near Seaview Ave. Beach & Dowses Beach! ! Seaview Avenue/ Wianno Area Of Osterville! Open Concept Cape/ Close To The Small But Beautiful Seaview Ave Beach, Dowses Beach, Or Go To All Of The Many T...

from

$243

/ night

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Osterville Massachusetts Vacation Rentals - Home
1 / 48

Osterville Home
11 BR / 8 BA / Sleeps 20 11 20 7 night min stayHome / 11 Bedrooms / Sleeps 20
11 bedrooms 8 bathrooms Sleeps 20
High Speed Internet • Dishwasher • Microwave
Wonderful old world charm! This 11 bedroom home with a private beach is perfect for a large family gathering. Offering a tennis court and Basketball hoop, a beach house on the sand with an enclosed outdoor shower, a d...

from

$1,786

/ night

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Osterville Massachusetts Vacation Rentals - Home
1 / 52

Osterville Home
10 BR / 12 BA / Sleeps 20 10 20 7 night min stayHome / 10 Bedrooms / Sleeps 20
10 bedrooms 12 bathrooms Sleeps 20
High Speed Internet • Dishwasher • Microwave
Beachfront estate custom built in 2005 with path to a private beach. This home has glorious ocean views from most all of the rooms and there is a dune path to your own private beach on Nantucket Sound just past the cotta...

from

$2,071

/ night

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Osterville Massachusetts Vacation Rentals - Home
1 / 24

Osterville Home
7 BR / 7 BA / Sleeps 14 7 14 7 night min stayHome / 7 Bedrooms / Sleeps 14
7 bedrooms 7 bathrooms Sleeps 14
High Speed Internet • Dishwasher • Microwave
Stunning seven bedroom home with heather pool and large backyard, main kitchen and caterers kitchen side by side. There is a sun room porch overlooking the back yard as well as a large deck. Lower level features a dance...

from

$1,571

/ night

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