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Holiday Rentals in Osterville

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    Travellers to Osterville are booking June dates now. Secure your holiday rental today, and have the perfect trip.
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    2 Bedrooms, Sleeps 4Quick View
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    3 Bedrooms, Sleeps 6Quick View
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    Charming three bedroom home in Osterville with an open floor plan. First floor master with an en-suite bath, spacious dining room, three-season glassed sun room overlooking a fully fenced yard. The two additional large bedrooms share the upstairs bathroom. This home also offers central air and the...
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    Osterville, Cape Cod
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 8Quick View
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    You get home from one of the beaches the complimentary beach pass allows you to visit, then washing off the sand in your enclosed outdoor shower. Relax on the sun splashed outdoor deck with your guests while enjoying a cold refreshing beverage and a delicious meal prepared on the gas grill. In the...
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    Osterville, Cape Cod
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 6Quick View
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    About this property
    This quaint affordable old world charm Osterville rental home is not far from the village and close to Dowses Beach. There are three bedrooms: 1. king bed 2. king bed and 3. queen bed. Two full baths and one half bath. Relax on the back deck with gas grill and nice private yard. Private setting on...
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    Osterville, Cape Cod
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 6Quick View
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    • Grill
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    Pet friendly
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    About this property
    SOUTH of RTE. 28 ~ OSTERVILLE !! BEACH PASS! Come enjoy this NEWLY REMODELED bright & sunny vacation home on a quiet street in lovely Osterville Woods! Quick access to beautiful Dowses Beach on Nantucket Sound (BEACH PASS PROVIDED ) Joshua s "cystal clear" Pond & the charming quaint village of...
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    Osterville, Cape Cod 02649
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    6 Bedrooms, Sleeps 13Quick View
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    About this property
    This wonderful Osterville home overlooking Neck Pond is a great private getaway. Located across from the Wianno Golf Club, this is an ideal location. Not far from the village and Dowses Beach. The house, set on a private acre, has a lovely porch, six bedrooms and four baths, a living room, family...
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    Osterville, Cape Cod
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 13
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    6 Bedrooms, Sleeps 12Quick View
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    About this property
    Located in the prestigious gated community of Oyster Harbors. This Cape Cod rental home features a newly renovated kitchen with all new appliances, first floor master suite, two staircases leading to four more bedrooms and two full baths. There is a one bedroom apartment on the property included in...
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    Osterville, Cape Cod
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    1 Review
    4 Bedrooms, Sleeps 8Quick View
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    Pet friendly
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    Excellent of 5 bubbles
    Reviewed 14 October 2013
    My family and I spent a week in this property in August 2013, as part of a 2 week vacation from the UK. In short, the property more than lived up to our hopes: fantastically...
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    About this property
    Bright & lovely, recently decorated/furnished home on almost 3 acres in Osterville's coveted SEAPUIT enclave on North Bay. Main House has Central A/C and 3 ensuite bedrooms. The 4th BR is in the STUDIO COTTAGE, available as an OPTION for additional $700 per week (summer season), if Option is...
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    Osterville, Cape Cod 02655
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    10 Bedrooms, Sleeps 20Quick View
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    About this property
    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 cottage. New for 2017: heated pool! The main home has six elegant bedrooms, most...
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    Osterville, Cape Cod
    Holiday Rental House - 10 Bedrooms, 12 Bathrooms, Sleeps 20
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    5 Bedrooms, Sleeps 8Quick View
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    About this property
    Private gated community rental home surrounded by water in prestigious Oyster Harbors. This Shingle Cottage style home was built in 2004 and comes with a sandy beach area as well as amazing attention to details. Over 3100 square feet with grand entry and open floor plan, every room in the house is...
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    Osterville, Cape Cod
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 4Quick View
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    Pet friendly
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    About this property
    Wonderful location! Close to Dowses Beach and not far from Main Street, also close to Wianno Golf Course and Crystal Lake! This lovely two bedroom, one bath home sits on a quiet village lane. Enjoy casual elegance and an open floor plan with wood floors, living room and separate den area. Fully...
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    Osterville, Cape Cod
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, Sleeps 6Quick View
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    About this property
    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-suite bath with soaking tub and steam shower. Second bedroom has two queen beds...
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    Osterville, Cape Cod
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 4Quick View
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    About this property
    This is the most charming and updated cottage in the "village" that you will find! Just 1 block to all Osterville shops and restaurants. This stunning little two bedroom gem is totally turn key with custom and designer details throughout. The pictures say it all! central air, gas fireplace,...
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    Osterville, Cape Cod
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    6 Bedrooms, Sleeps 12Quick View
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    • Internet Access
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    • Hot Tub
    • Waterfront
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 swim in the heated pool. Make plans to take your boat out for the day to nearby...
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    Osterville, Cape Cod
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    5 Bedrooms, Sleeps 12Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    About this property
    This beautiful five bedroom home is nestled on a private three acre lot in the desirable area of Seapuit, close to Osterville village center. The exterior is highlighted by lush landscaping, fruit trees, a stunning swimming pool and pool house with kitchenette. The interior features gleaming oak...
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    Osterville, Cape Cod
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 12
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    4 Bedrooms, Sleeps 8Quick View
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    Smoking allowed
    About this property
    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 town of Barnstable public beaches, as Barnstable BEACH PASS is included....
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    Osterville, Cape Cod 02655
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 6Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Do you have allergies? If so, then this Osterville rental home is the perfect home for you. This house is completely scent free. Walk to Main Street to Osterville village and it is only 1.5 miles from Dowses Beach. This home has a well-appointed kitchen that opens to a dining area and living room...
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    Osterville, Cape Cod
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 8Quick View
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    Smoking allowed
    About this property
    Lovely four bedroom, two bath rental home in the heart of Osterville. Short stroll to village and not far from Dowses Beach with a beach pass provided. Two bedrooms, living room, dining room and sitting area on the first level as well as a full bath. Second level has two bedrooms and second full...
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    Osterville, Cape Cod
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 9Quick View
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    • Satellite TV
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    • Wi-Fi
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Picturesque, completely renovated 8 room seaside home is surrounded by stunning blue hydrangeas & roses. Just 1.5 blocks to Osterville center & walk/bike to harbor and beach; Light and airy with a nautical theme and open floor plan. Gourmet kitchen. The space This newly renovated colonial home...
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    Osterville, Cape Cod 02655
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    6 Bedrooms, Sleeps 10Quick View
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    About this property
    Great home located between Dowses 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 with a casual eating area, comfortable living room, two full baths, two bedrooms and...
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    Osterville, Cape Cod
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, Sleeps 10Quick View
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    • Grill
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    • Waterfront
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    About this property
    Unique opportunity to enjoy panoramic views of Cotuit and North Bay from this stunning home located in prestigious Oyster Harbors on the aptly named Sand Point. With an eye towards preserving the Cape Cod charm of the property, owner and builder created a home that offers every modern luxury in a...
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    Osterville, Cape Cod
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, Sleeps 12Quick View
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    About this property
    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! Large open kitchen and dining room as well as a den with two bedrooms on the first floor and a full bath and half bath. Second...
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    Osterville, Cape Cod
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    7 Bedrooms, Sleeps 14Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Enter the private drive towards your Cape Cod rental home. This stunning seven-bedroom home has a lot to offer for your summer vacation. Walk into the foyer to large open floor plan including, eat in Gourmet kitchen, with second additional kitchen nearby, formal dining room, living room and den....
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    Osterville, Cape Cod
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    3 Bedrooms, Sleeps 5Quick View
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    This rental is as cute as a button. Located between Dowses Beach and the village. A truly hidden gem! There are three bedrooms and one full bath. The first level has a queen bedroom, dining/living area, kitchen and full bath. There are two bedrooms upstairs. One with a twin and the other with two...
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    Osterville, Cape Cod
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    About this property
    BEAUTIFUL SEAPUIT HOME IN OSTERVILLE NEAR VILLAGE EXQUISITE 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 love seat/sofa bed in the Den) 3 .5 baths~each bedroom has it s own private...
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    Osterville, Cape Cod 02655
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    8 Bedrooms, Sleeps 20Quick View
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    Kid friendly
    Smoking allowed
    About this property
    Cape Cod charm in every space of this home. This Osterville private compound has lots of living areas and expansive water views from both main home and boathouse. This Estate offers a beach, tennis court, hot tub and deep-water dock. Close to Osterville village and all it has to offer. There are...
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    Osterville, Cape Cod
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 20
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    11 Bedrooms, Sleeps 20Quick View
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    Wonderful old world charm! This 11 bedroom home with a private beach is perfect for a large gathering. Offering a tennis court and basketball hoop, a beach house on the sand with an enclosed outdoor shower, a deck for watching the magnificent Cape Cod sunsets or simply relaxing during or after...
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    Osterville, Cape Cod
    Holiday Rental House - 11 Bedrooms, 8 Bathrooms, Sleeps 20
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    5 Bedrooms, Sleeps 10Quick View
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    About this property
    Cape Cod waterfront home in Osterville. Magnificent sun-filled summer home with a private deep water dock on East Bay and a short walk from both beautiful Dowses Beach and from Osterville village for easy access to fine dining and quaint shops. A private retreat that offers panoramic views of the...
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    Osterville, Cape Cod
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    6 Bedrooms, Sleeps 10Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    About this property
    The very best of old + new! 4500+ square feet of vintage Cape charm conscientiously updated for today’s lifestyles. 1930’s summer home on Nantucket Sound. Private beach with ocean views from every room. Modern amenities include heated pool, full A/C, updated eat-in kitchen and baths, flat screen...
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    Osterville, Cape Cod
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, Sleeps 8Quick View
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    About this property
    Its always nice to be a short stroll to the village and not far from the beach. This Osterville rental home has these qualities and more. Large open concept kitchen and eating area with TV, formal living room and den with additional flat screen TV, couch and bunk beds for a 4th sleeping area. There...
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    Osterville, Cape Cod
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    9 Bedrooms, Sleeps 15Quick View
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    Quiet luxury on the waters edge. Feel at one with the sand, surf, and sun while luxuriating on your own beach area surrounded by private and lush 26 acres in this exclusive gated paradise that is Oyster Harbors. Complete with a tennis court, beach house, dock and beach area. This property provides...
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    Osterville, Cape Cod
    Holiday Rental House - 9 Bedrooms, 9 Bathrooms, Sleeps 15
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    12 Bedrooms, Sleeps 15Quick View
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    About this property
    Cape Cod charm at its best and most elegant. Exquisite Ocean front home with private beach making for an ideal vacation. There are 12 bedrooms and large open areas for gathering. Kitchen, pantry, dining room and sitting room overlooking the water with pool table. There is a living room with TV and...
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    Osterville, Cape Cod
    Holiday Rental House - 12 Bedrooms, 8 Bathrooms, Sleeps 15
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    4 Bedrooms, Sleeps 10Quick View
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    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 four bedroom, 3.5 bath home is perfectly located in the heart of Wianno and within walking distance to Osterville village with convenient shopping,...
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    Osterville, Cape Cod
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    About this property
    NEW LISTING! Dog Friendly~BEAUTIFUL VIEWS OF NORTH BAY in Special Seapuit Area of Osterville w/DOCK rights!! First Offering: 2017 season ! In the lovely enclave known as "Seapuit" in Osterville; come discover this newly built (2016) BEAUTIFUL Carriage House with STUNNING WATERVIEWS of North Bay!...
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    Osterville, Cape Cod 02655
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, Sleeps 7Quick View
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    About this property
    This jewel box of a home is filled with treasures from an airy living room with windows on three sides, a charming dining room, an outstanding kitchen plus a den on the first floor. The second floor has three bedrooms and a study. There are five full baths and a new elevator to make it very...
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    Osterville, Cape Cod
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 7
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    3 Bedrooms, Sleeps 5Quick View
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    About this property
    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 appointed and comes with a private tennis court, large patio with a fire pit, and incredible views....
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    Osterville, Cape Cod
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 5
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    4 Bedrooms, Sleeps 8Quick View
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    • Grill
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    This home has been totally renovated from top to bottom for the 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 porch with flat screen and office area. Great outside entertainment area with built...
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    Osterville, Cape Cod
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 6Quick View
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    About this property
    Stroll to the village from this lovely three bedrooms, three full bath home. Large open floor plan on first level with kitchen, dining, living room, bedroom and full bath. Go upstairs to two more bedrooms and two additional full baths. There is central air for your comfort as well as a screened-in...
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    Osterville, Cape Cod
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 8Quick View
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    Bright, lovely secluded home on almost three acres in prestigious Seapuit enclave of large estate homes. Main house has three bedrooms (each with private bath). Meticulously maintained with beautiful landscaping, serenity, and privacy. Royal Barry Wills inspired home is walking distance to bay...
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    Osterville, Cape Cod
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    6 Bedrooms, Sleeps 12Quick View
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    Where else can you stroll to the Osterville 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 backyard to the well thought out kitchen with every amenity for the gourmet...
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    Osterville, Cape Cod
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, Sleeps 8Quick View
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    Just a few steps to Osterville village center! Well-appointed and comfortable. New custom second floor master suite has been added. Spacious deck overlooking golf and Bay! This home backs up to the 6th hole of the Wianno Golf Course and is only a few houses away to Bay access at end of the street....
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    Osterville, Cape Cod
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    • Satellite TV
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    • Private Outdoor Pool (Unheated)
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    About this property
    Sit by the heated pool and relax after a day at Dowses beach or take a stroll to Osterville village. This classic Cape Cod home is situated in the heart of Wianno on a secluded and lushly landscaped approx. acre of land. Great deck for entertaining stretching along the back of the house with gas...
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    Osterville, Cape Cod
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 8Quick View
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    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 three bedrooms and a full bath on first floor. Living room, family room and eat-in kitchen. There is a spacious deck off the kitchen, outdoor shower...
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    Osterville, Cape Cod
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, Sleeps 10Quick View
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    Robert Paul Properties rental home. A lovely home in the gated community of Oyster Harbors. This home features a combination of both older well cared for and casual spaces, perfect for entertaining or quiet enjoyment. The first floor offers a bedroom (queen bed) and bath with separate entrance, a...
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    Osterville, Cape Cod 02655
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    4 Bedrooms, Sleeps 9Quick View
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    About this property
    New construction with 9 foot ceilings. This stunning Osterville rental home has spared no detail in comfort and luxury. Gourmet kitchen and seating area overlooks great back yard with seating on deck and fire pit. First floor en-suite master with queen bed, fireplace living room with TV and powder...
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    Osterville, Cape Cod
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 9
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    Oyster Harbors Classic Cape Retreat & Guest Cottage- Located on Oyster Harbors, a private island in a gated community with 24 hour security, one of Osterville's premier neighborhoods. This 1926 home features a newly renovated kitchen ( 2016) with all new appliances. Also includes first floor master...
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    Osterville, Cape Cod 02655
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, Sleeps 8Quick View
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    Best of both worlds, close to Dowses Beach and walk to Osterville village. First floor has large open space with eat-in kitchen, dining area, fire placed living room, half bath, and master bedroom with king bed and full bath. Walk up to the second floor for three more bedrooms and a full bath as...
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    Osterville, Cape Cod
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 8Quick View
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    • Satellite TV
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    • Washer
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    Pet friendly
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    Smoking allowed
    About this property
    NEW LISTING! Small Non-Shedding DOGS considered! Darling Newly Remodeled three bedroom 1.5 bath Ranch w/BEACH PASS!! 1st Offering! 2017 Season! NEWLY remodeled Open Concept three bedroom, 1.5 bath ranch with central A/C and a beautifully appointed new kitchen that includes a large breakfast...
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    Osterville, Cape Cod 02655
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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