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Holiday Rentals in Osterville, MA

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    Travellers to Osterville are booking June dates now. Secure your holiday home today, and have the perfect trip.
    1 / 18
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 18
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    1 / 31
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    1 / 53
    6 Bedrooms, 4 Bathrooms, Sleeps 13 | Quick View
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    About this property
    This wonderful Osterville home overlooking Neck Pond is a great private get-away. 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... View all property information
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    Osterville, Cape Cod
    1 / 38
    7 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    • Private Outdoor...
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    About this property
    Luxury at its best! This stunning home in the gated community of Oyster Harbors has a main home with 4 plus bedrooms, media room, formal dining room, living room, gourmet kitchen, den/library, and a deck overlooking the expansive back yard. There is a heated pool as well as a cabana pool house that... View all property information
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    Osterville, Cape Cod
    1 / 19
    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Rental home situated at the end of a long and winding driveway leads to this expansive Cape style home offering over 3,900 square feet of living space. Fronting Bog Pond and with views of North Bay in the distance, this rental home offers not only privacy but a heated inground pool and large yard.... View all property information
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    Osterville, Cape Cod
    1 / 13
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick 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 2. King and 3. Queen and two full baths and one half bath. Relax on the back deck with gas grill and nice private yard. The owner provides a beach... View all property information
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    Osterville, Cape Cod
    1 / 26
    6 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    The very best of old + new! 4500+ sq. ft. of vintage Cape charm conscientiously updated for today’s lifestyles. 1930’s family 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... View all property information
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    Osterville, Cape Cod
    1 / 22
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Charming home in Osterville with an open floor plan. 3 bedrooms. 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... View all property information
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    Osterville, Cape Cod
    1 / 12
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Wonderful location! Close to Dowses and not far from Main Street, also close to Wianno Golf Course and Crystal Lake! This lovely 2 bedroom, 1 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 equipped... View all property information
    Location Information
    Osterville, Cape Cod
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    1 / 24
    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    About this property
    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 studio as well as 2 additional bedrooms. First floor master suite and... View all property information
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    Osterville, Cape Cod
    1 / 25
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Pet-friendly
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    About this property
    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... View all property information
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    Osterville, Cape Cod
    1 / 52
    10 Bedrooms, 12 Bathrooms, Sleeps 20 | Quick View
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    • Grill
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    • Pet-friendly
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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. The main home has 6 elegant bedrooms, most with waterfront balconies. Entry... View all property information
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    Osterville, Cape Cod
    1 / 13
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    In desirable Wianno Circle location of Osterville. Close to Dowses beach and village. Great location for this three bedroom, two full bath home. Deck, large yard with gas grill and patio set. This rental has window air units in the bedrooms and provides a town beach pass. Additional amenities... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 26
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Set down a quiet lane in a prime Osterville village location sits this spacious four bedroom Ranch. Enjoy deeded beach and water rights on North Bay with access to Nantucket Sound, only a short walk from the home. The light filled home features an updated kitchen and an ideal floor plan with the... View all property information
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    Osterville, Cape Cod
    1 / 21
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Porch
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    • Satellite TV
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    • Pet-friendly
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    About this property
    This home was designed by a Well Known Architect. Walk to Main Street in Osterville and 1.5 miles from Dowses Beach. This home has a well-appointed kitchen with an open floor plan. There is a deck with automatic screens, central air and WIFI. This is an allergen free home. House is supplied with... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 17
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    • Pet-friendly
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    • ?
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    About this property
    Robert Paul Properties rental home. This lovely three bedroom, two full bath home is not far from Dowses beach, Osterville Village shops, Restaurants and Kelly Armstrong Park! Private back yard with gas grill and tastefully appointed. Beach pass provided. Additional amenities include: coffee... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 19
    5 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Porch
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
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    • Smoking allowed
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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... View all property information
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    Osterville, Cape Cod
    1 / 22
    5 of 5 stars (1) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Patio
    • DVD Player
    • Balcony
    • Air Conditioning
    • Washer
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Osterville, Cape Cod
    5 of 5 stars 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 well...
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    1 / 15
    5 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
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    • Smoking allowed
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    About this property
    One month minimum. No weekly inquiries, please. Completely renovated in 2005, this beautiful 5 bedroom home is nestled on a private 3 acre lot in the desirable area of Seapuit, close to the village center. The exterior is highlighted by lush landscaping, fruit trees, a stunning swimming pool and... View all property information
    Location Information
    Osterville, Cape Cod
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    1 / 48
    11 Bedrooms, 8 Bathrooms, Sleeps 20 | Quick View
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • ?
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    • Smoking allowed
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    About this property
    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 deck for watching the magnificent Cape Cod sunsets or simply relaxing during or... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 26
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Grill
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    • Waterfront
    • DVD Player
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    • Private Outdoor...
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
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    • Smoking allowed
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    About this property
    This home is located in prestigious Oyster Harbors. The home boosts a heated pool, dock and beach area at the home. There is privacy and luxury in this newer updated home. The first level has a large master suite with full bath with soaking tub. There are four bedrooms and two sitting areas on the... View all property information
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    Osterville, Cape Cod
    1 / 25
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick 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... View all property information
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    Osterville, Cape Cod
    1 / 21
    8 Bedrooms, 8 Bathrooms, Sleeps 20 | Quick View
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    • Parking
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
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    • Smoking allowed
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    About this property
    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, tennis court, hot tub and deep-water dock. Close to Osterville village and all... View all property information
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    Osterville, Cape Cod
    1 / 17
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    • Patio
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 27
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Balcony
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    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Terrace
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    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 Dowses Beach on Nantucket Sound (BEACH PASS PROVIDED ) Joshua s 'cystal clear' Pond... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 13
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Pet-friendly
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    • Smoking allowed
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    About this property
    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 amenities include: coffee maker, outside shower - enclosed, pets considered,... View all property information
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    Osterville, Cape Cod
    1 / 41
    11 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    About this property
    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, beautiful gardens, mature vegetation and stone walls. Situated down a long driveway,... View all property information
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    Osterville, Cape Cod
    1 / 24
    12 Bedrooms, 8 Bathrooms, Sleeps 15 | Quick View
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    • Internet Access
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    • Pet-friendly
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    About this property
    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 around porch, and an expansive yard overlooking the ocean. Additional amenities... View all property information
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    Osterville, Cape Cod
    1 / 35
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Porch
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    • Pet-friendly
    • Child-friendly
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    About this property
    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 porch with flat screen and office area. Great outside entertainment area with... View all property information
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    Osterville, Cape Cod
    1 / 23
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Private Garden
    • Air Conditioning
    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Elf Hill Cottage is comprised of two double bedrooms, a third bedroom with two twin beds and a daybed for a child, two full bathrooms, a living room, dining room and sun room. There is an automatic garage. The house has been freshly painted, has hardwood floors upstairs and down, and is... View all property information
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    Osterville, Cape Cod
    1 / 21
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • ?
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    About this property
    Located in the prestigious gated community of Oyster Harbors. Features include a newly renovated kitchen with all new appliances, first floor master suite, two staircases leading to four more bedrooms and two full baths. This comfortable home is great for a large family and guests, features two... View all property information
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    Osterville, Cape Cod
    1 / 21
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    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 and a great large floor plan. One queen master and a second bedroom with two twin... View all property information
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    Osterville, Cape Cod
    1 / 24
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • ?
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    About this property
    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 level has two bedrooms and another full bath. Nice patio and fire pit in the... View all property information
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    Osterville, Cape Cod
    1 / 19
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • ?
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    About this property
    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 privacy. Royal Barry Wills inspired home is walking distance to bayfronts, Joshua’s Pond... View all property information
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    Osterville, Cape Cod
    1 / 16
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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 and eat-in kitchen. There is a spacious deck off the kitchen and a private back... View all property information
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    Osterville, Cape Cod
    1 / 16
    6 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    About this property
    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 with a casual eating area, comfortable living room, two full baths, two... View all property information
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    Osterville, Cape Cod
    1 / 14
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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 provided. Additional amenities include: coffee maker, outside shower - enclosed,... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 17
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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.... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 24
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Satellite TV
    • Porch
    • Grill
    • DVD Player
    • Internet Access
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    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’s Vineyard. Beautiful sunrises and sunsets. Deep water dock with access to fast... View all property information
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    Osterville, Cape Cod
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    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 and within walking distance to Osterville village with convenient shopping,... View all property information
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    Osterville, Cape Cod
    1 / 15
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
    • Patio
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    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 shops and wonderful restaurants lining Osterville s Main Street. Additional... View all property information
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    Osterville, Cape Cod
    1 / 8
    6 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    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 the well thought out kitchen with every amenity for the gourmet chef. Choose... View all property information
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    Osterville, Cape Cod
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    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 and bay! This home backs up to the 6th hole of the Wianno Golf Course and is... View all property information
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    Osterville, Cape Cod
    1 / 20
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Satellite TV
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    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! Providing plenty of space for family and friends. Large open kitchen and dining room as well as a den with two bedrooms on the... View all property information
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    Osterville, Cape Cod
    1 / 3
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    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 offers a first floor master bedroom with custom built ins and a private bath. A... View all property information
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    Osterville, Cape Cod
    1 / 12
    3 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • Parking
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    • Waterfront
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    • Pet-friendly
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    • ?
    • ?
    • Smoking allowed
    • ?
    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... View all property information
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    Osterville, Cape Cod
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Central Heating
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    • x
    • Smoking allowed
    • x
    About this property
    This stunning waterfront home sits on a small bluff overlooking Cotuit Bay, Sampson's Island (Deadneck), and Martha's Vineyard on a clear day. Easy access to its own private beach and a deep water dock can accommodate boat 40+ feet with electrical hook-up. There are kayaks, a paddleboard and... View all property information
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    Osterville, Cape Cod
    1 / 12
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Private Garden
    • Satellite TV
    • Air Conditioning
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    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Welcome to what we affectionately refer to as "The Black Pearl," a vintage home located in one of the Cape's most coveted locations. Oyster Harbors is a private island only accessible to residents, club members & guests! A deep water dock with access to fast water in minutes. Enjoy views of... View all property information
    Location Information
    Osterville, Cape Cod
    1 / 39
    5 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Satellite TV
    • DVD Player
    • Parking
    • Internet Access
    • Waterfront
    • Grill
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    This magnificent waterfront residence on Oyster Harbors has the feeling and look of a European estate. With a stucco exterior and extensive gardens, the home has distinct features and is stunning. Completely remodeled inside. The uniqueness continues on the interior with high vaulted ceilings and... View all property information
    Location Information
    Osterville, Cape Cod