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Holiday Rentals and Homes in Oak Bluffs, MA

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    277 Holiday Rentals in Oak Bluffs
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    €1,615
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    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    About this property
    Tucked behind a beautiful hedgerow, this restored bungalow is just up the hill from Oak Bluffs center and on the outskirts of East Chop. Comfortable and loaded with personality, the large living room opens to a breezy sleeping porch. A simple yet well-stocked kitchen is graced by a lovely dining... View all property information
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    €2,122
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    Owner Transfer Ferry Tickets - Please Inquire 2010 newly renovated, features central AC, all new kitchen, 2 new baths and hardwood floors on the living level. Open kitchen, living and dining areas are flooded with light from the floor to ceiling windows and opens to a large wrap around deck with... View all property information
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    €2,953
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    Gracious 5 bedroom in-town victorian offers easy access to shopping, ferry, park with basketball and tennis and beach. This home has been lovingly maintained and restored to it's prior elegance. Enjoy cocktails on the beautiful three season porch. Additional amenities include: coffee maker,... View all property information
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    €1,338
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Cozy cottage completely renovated in 2005. New hardwood floors, brand new kitchen, vaulted ceiling and painted throughout. Ceiling fans in all bedrooms, two ceiling fans in dining room and kitchen. All new furnishings with a cheery, cottage flair. Just a 10 minute walk to Circuit Avenue in Oak... View all property information
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    About this property
    Immaculate, waterview town house located in the desirable Sengekontacket Pond area of Oak Bluffs. Wonderful waterviews of Sengkontacket Pond and Nantucket Sound. This spacious unit offers a bright open airy feeling with three levels of living area. The main floor includes bedroom, living, dining... View all property information
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    €2,768
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    About this property
    MVVR EXCLUSIVE: Custom crafted tri-level, this beautiful home features spacious open living spaces, hardwood floors throughout, 3 full baths, central A/C and WiFi. Exterior features include a large private deck at the back of the house, the perfect venue for summer dining or just relaxing with a... View all property information
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    €6,920
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    About this property
    Exceptional location for this immaculately kept Victorian on Waban Park next to the Seaview Condos. Walk across the street to the beach. Walk to town. Walk right out the door to the park with ample space for children to play. The house is tastefully and colorfully decorated. The newly upgraded... View all property information
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    About this property
    Quietly tucked away in prestigious Farm Neck Golf Club, this contemporary has sweeping waterviews of Sengekontacket Pond, State Beach and the Atlantic, as well as the 8th hole on the golf course. Situated on almost two landscaped acres, there are large wrap-around decks that afford multiple... View all property information
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    OAK BLUFFS BAYES HILL: A/C, linens, towels and beach towels, WIFI Close to everything but just enough out of the way to be a peaceful family vacation destination on Martha's Vineyard. Large grassy yard, wide open porch, and private deck. Additional amenities include: longitude: -70.5982, living... View all property information
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    OAK BLUFFS EAST CHOP, Come relax and stay at our dream come true. TRANSFERABLE FTS FOR MANY WEEKS CALL FOR INFO Our completely renovated cottage sits overlooking one of Oak Bluffs many parks with views of Vineyard Sound and Cape Cod. The cottage has three bedrooms and one and a half baths:all... View all property information
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    €3,599
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    Absolutely delightful Oak Bluffs Victorian with colorful and charming decorating touches. Spacious and homey, this house has been cared for and cherished. Old world charm with all of today's necessities combined transport you to another era and give you all the comfort of modern times. Sleeps 8... View all property information
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    A charming early 1900s cottage in Oak Bluffs, just completely renovated. Walk to town, park, beach and steps to library. Two bedroom, one very large full bathroom. Spacious working, eat-in-kitchen with all stainless steel appliances and washer/dryer. Separate dining area. Cable, TV, Wi-fi, Ipod... View all property information
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    €1,384
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    This cozy 2 bedroom has lots of natural sunlight with cheerful updated decor. Perfect for a family of 4 with extra room on sleeping porch for nanny or additional family member. Just a short walk to town, beach and parks. Additional amenities include: coffee maker, bakeware, lobster pot, dishes,... View all property information
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    About this property
    A fully renovated four bedroom home with three and a half baths and separate garage, landscaped lot and a private dock. Dock can accommodate up to a 25 foot motor boat and is accessible to Vineyard Sound. Family room with cable TV, deck, fully equipped kitchen, wood burning stove, and a 2 person... View all property information
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    €3,091
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    About this property
    Charming Gingerbread Cottage located in the Tabernacle area of Oak Bluffs. A short stroll brings you to Oak Bluffs Center with shops, family and fine dining, harbor area, bandstand park, and Ink Well Beach. Recently updated, this house features a modern eat in kitchen opening to the back deck and... View all property information
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Quintessential Vineyard House and Guest House in prestigious Harthaven neighborhood on Farm Pond. Three large bedrooms and two full baths in 'Frank Lloyd Wright' style main house with huge deck, outdoor shower, cable TV/VCR/DVD, and A/C. Additional huge bedroom, full bath and kitchen in large Guest... View all property information
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    €6,920
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    Tucked away on the shores of The Lagoon, this deluxe waterfront retreat has been designed with an open layout to maximize grand water views and sunsets from its decks, screened porch and most rooms. The main level of Crow's Nest features a stylish wrap-around mahogany deck, and Great Room with open... View all property information
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Spectacular views across Sengekontacket Pond. Tastefully furnished with all the amenities. Split A/C in the main living area. Split A/C in the Master Bedroom. Association tennis courts. Centrally located just a short drive to three towns, beaches, dinning, golf and shopping. Amenities and... View all property information
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    €2,999
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    About this property
    Amenities and Features include... Boutique Sweet with Designer Interior, Large Screened Porch, AC all Bedrooms, 15 Minute Walk to Oak Bluffs Center and Inkwell Beach Additional amenities include: coffee maker, patio table and chairs, washer / dryer, landscaped, porch - screened, outside shower -... View all property information
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    About this property
    Enjoy the charm of a Vineyard cottage with all the amenities of today. This 3 bedroom house has brand new furnishings for 2015. It is in a quiet neighborhood not far from Oak Bluffs center and its harbor. The house is also close to the bike path. The house has an open floor plan with a large... View all property information
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    About this property
    Set in a quiet community of homes just on the outskirts of OB, this outstanding home provides a peaceful get away yet is just a short drive to town center. The use of coastal colors and upscale furnishings throughout combine to make this gorgeous Oak Bluffs summer home a cut a above. Expansive... View all property information
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    About this property
    Owner Transfer Ferry Tickets - Please Inquire Situated on quiet side street with a 15 minute walk or a 5 minute drive to town and beach, this light filled cape offers visiting families a well equipped vacation reprieve with comfortable living areas, modern kitchen, AC in all bedrooms. The first... View all property information
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    About this property
    Just take your morning coffee down the steps to your beach and decide what you will do for the rest of the day. Probably you will not leave this fantastic property for the entire length of you stay on the vineyard. If you do decide to go and venture out, you are so very close to Oak Bluffs or... View all property information
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    About this property
    This newer home faces Nashawena Park, one of Oak Bluffs loveliest neighborhoods. From this excellent location, you are within walking distance of Inkwell Beach and all that Circuit Avenue has to offer - shops, excellent restaurants, the busy harbor area and ferry terminals, movies and nightly live... View all property information
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    About this property
    This beautifully designed home features four bedrooms, three full and one half baths. The living spaces include a formal dining room, living room and sun porch and a deck that lead out to nicely landscaped grounds. Other Amenities: iPhone Dock & Play Station 3 Additional amenities include: beach... View all property information
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    About this property
    Waterview Farm is a private association with wonderful meadow and water views. It is adjacent to Farm Neck Golf and Tennis Club, which is open the public. There is access to Sengekontacket Pond to launch canoes and kayaks from the private association beach. This is also a great spot for children to... View all property information
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    About this property
    Beautiful four bedroom house in the prestigious Farm Neck area overlooking a lovely lawn to a large tidal pond. This home offers an open floor plan so the whole family can be together. The kitchen and living areas open up to a wonderful deck so you can enjoy the views of Sengekontaket Pond. There... View all property information
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Open, airy contemporary Cape. All newly furnished, three bedrooms, 2 bathrooms. Ceiling fans in all bedrooms. A short 15 minute walk to Oak Bluffs Center and Beach, shopping, and dining. Sidewalks connect to miles of bike paths. Amenities and Features include... Walk to Town. Hi Speed Internet.... View all property information
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    East Chop three level modern home with waterviews from each level, the second level deck makes outdoor activities such as eating an enjoyable experience. Amenities and Features include... EAST CHOP, WATERVIEW, WALK TO TOWN, CENTRAL AIR CONDITIONING, WI-FI Additional amenities include: coffee... View all property information
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    About this property
    Waterfront Compound on Lagoon with panoramic water views. The main house features an open and spacious living area with comfortable furnishings, a dining area and a spacious kitchen with new appliances. The master bedroom with king bed has a private bath and opens onto a private deck. The second... View all property information
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    About this property
    Enjoy beautiful waterviews of Farm Pond and Nantucket Sound while relaxing on the back deck. This vintage Vineyard Cottage located in the private Harthaven association has access to 2 private association beaches as well as a private tennis court. Additional amenities include: games, coffee maker,... View all property information
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    About this property
    Light filled, spacious and above it all. This quiet residence is situated in Oak Bluffs' exclusive Meadow View Farm community. Close to bike paths (bikes come with the rental) and the MVTA bus and close to Sengekontacket for Pond bathing and kayaking. Additional amenities include: beach chairs,... View all property information
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    About this property
    Happy House sleeps 9 within a mile of the center of Oak Bluffs. Charming eclectic restored bungalow hidden away behind a mature hedgerow. First floor features a large open living and dining area, fully equipped kitchen and a wonderfully cheery sleeping porch with a full and single bed. There is... View all property information
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    6 Bedrooms, 2 Bathrooms, Sleeps 11 | Quick View
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    • Dishwasher
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
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    About this property
    Amenities and Features include... In-Town, Walk to Beach, Wifi Internet Additional amenities include: coffee maker, patio table and chairs, fans - portable, lobster pot, washer / dryer, cd player, landscaped, outside shower - enclosed, phone ld block, outdoor furniture, ironing board. View all property information
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Dishwasher
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Wheelchair access
    • Elder access
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    About this property
    Located in Oak Bluffs this house is walking distance to town, the marina and nestled in the Copeland/Arts District area also walking distance to the historic Gingerbread cottages.  A 15 min. walk to the Inkwell beach and less than a 5 min. drive.  Four bedrooms and two full baths.  There is a nice... View all property information
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    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Dishwasher
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    • Satellite TV
    • Water Views
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Wheelchair access
    • Elder access
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    About this property
    OAK BLUFFS, Waterview Farms: Waterview summer vacation family friendly reverse contemporary overlooking conservation land and Sengekontacket Pond and Nantucket Sound. Association beach. Easy access to bike path. Less than two miles to Oak Bluffs, State Beach and Oak Bluffs Harbor. Call for off... View all property information
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    €3,691
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Dishwasher
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    • Internet Access
    • Satellite TV
    • Water Views
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    OCEAN FRONT Oak Bluffs and still a walk into town. Relax on the front porch while you sip on an after beach cold beverage. Life at the beach! Charming completely renovated summer beach cottage. Great space for your family to be able to spread out and relax. House sleeps 10 comfortably. Cleaning fee... View all property information
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    €4,383
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    • Air Conditioning
    • Dishwasher
    • Dryer
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    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • x
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    About this property
    Luxury waterfront home with dock, deep water mooring, a private beach as well as deep water access and marina facilities close-by. Enjoy a commanding view of Lagoon Pond with gorgeous westerly sunsets - second to none! This home offers a spacious open floor plan providing a comfortable yet elegant... View all property information
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This four bedroom, three story home has plenty of space to relax with two decks and a spectacular third level master suite.  Located in a private neighborhood with easy access to walking trails and the bike path.  A short walk to 2 association tennis courts.  Minutes by car to beaches and towns and... View all property information
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    €2,722
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    6 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Dishwasher
    • Grill
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    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
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    About this property
    The Pennacook house in Oak Bluffs on the charming island of Martha's Vineyard is beautifully maintained, bright and sunny, with a large eat-in kitchen, living room, dining room, and library with WIFI. Play outside on the large lawn, relax in the hammock, watch sunset from the front porch and enjoy... View all property information
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    €2,537
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Satellite TV
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    • Suitable for children
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    About this property
    East Chop Gem~Sweet East Chop cottage perfectly appointed and beautifully kept. 2 Bedrooms, plus finished basement with sleeper sofa allow for plenty of room to rest and play.Downstairs ping pong, over-sized deck and forest views make this cottage fun and inviting. 1 full bath, and 1/2 bath, walk... View all property information
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    €2,676
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    • Air Conditioning
    • Dishwasher
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
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    About this property
    10 minute walk to Oak Bluffs center and beach area from this lovely modern vacation home. Enjoy all that the summer community of Oak Bluffs has to offer, quaint shops, fine and family dining, harbor front stroll where you will and array of dining establishments, all waterside, boat rentals and... View all property information
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    €1,642
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    • Dishwasher
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Exquisite 3 bedroom 3 bath home bordered by a large lovely landscaped yard. The exterior features a shady wrap around porch with porch rockers,a perfect place to get out of the sun, read a book and enjoy the peace and quiet of the surrounding area. The back of the house overlooking the large yard... View all property information
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    €4,613
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    5 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
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    • Dishwasher
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    • Internet Access
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Elder access
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    About this property
    Sengekontacket Oak Bluffs vacation destination: FOOTPATH TO PRIVATE ASSOCIATION SALTWATER DOCK. This spacious custom-built 10-room, 5-bedroom, (sleeps 10-12) 3 bath home in Oak Bluffs is equipped with 2 full kitchens, 2 decks and a large 3-season porch. Enjoy private association tennis courts, the... View all property information
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    €1,015
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
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    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This charming cape style residence is situated on a wooded lot near the bike path and just a short ride to town center and the ferry. The home features a first floor open design with a bright kitchen / dining / living area and hardwood floors. The first floor den has a full size bed and French... View all property information
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