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Holiday Homes and Apartments Oak Bluffs, MA

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    All 353 Rentals in Oak Bluffs
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    Travellers to Oak Bluffs are booking June dates now. Secure your holiday rental today, and have the perfect trip.
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    1 / 26
    5 Bedrooms / 3 Bathrooms / Sleeps 10
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    $3,677
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    4 Bedrooms / Sleeps 8
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    About this property
    Right in the heart of Oak Bluffs this four bedroom offers a close proximity to town and the beach. Shopping and restaurants just blocks away. A/C units in all bedrooms on second floor. Flat screen TV'S in family room and two master bedrooms. Additional amenities include: cleaning fee: $400, beach... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 7
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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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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    Located in Meadow View Farms with association tennis available for your use, and across from Farm Neck Golf Course. This newly furnished and attractively decorated home with hardwood floors is set on an acre of land. Just two miles from the center of town shopping, restaurants and the beach.... View all property information
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    1 / 14
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Lovely cape home, all newly refurnished for 2013. First level features an open floor plan in the Dining, Kitchen and Living area. The tastefully decorated living area features comfortable furnishings and a 36' screen tv. One bedroom with a double bed and a full bath complete the living level. 2nd... View all property information
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    1 / 13
    3 Bedrooms / 1 Bathroom / Sleeps 5
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    About this property
    Bright and newly remodeled classic summer cottage. Conveniently located just one mile from Oak Bluffs town center, Ink Well Beach, shops, fine and family dining, historic Flying Horses Carousel, public tennis courts, Bandstand Park and Oak Bluffs Harbor-front area. The professionally landscaped... View all property information
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    1 / 23
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    This lovely 3 bedroom home features an open floor plan on the living level, colorful decor, window ac in all rooms and a well equipped modern kitchen. The home is nicely situated in quiet neighborhood, on the outskirts of Oak Bluffs, convenient to all three down island towns and beaches and a short... View all property information
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    1 / 33
    5 Bedrooms / 4 Bathrooms / Sleeps 8
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    About this property
    Custom Crafted Luxury Home on Farm Neck Golf Course This gorgeous 5 bedroom home overlooks the golf course and Sengekontacket Pond. Large family living spaces include a great room with soaring ceilings opening to the patio as well as a large TV/family room. The expansive kitchen is custom designed... View all property information
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    1 / 14
    4 Bedrooms / Sleeps 9
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    About this property
    HIDDEN COVE - lovely four bedroom home with views of Sengekontacket pond. Contemporary Martha's Vineyard house with open kitchen, living and dining. Air conditioning. Large deck off back of house taking full advantage of the view. Convenient to both Oak Bluffs and Edgartown Center. Association... View all property information
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    1 / 19
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    • Shared Outdoor Pool...
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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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    1 / 34
    6 Bedrooms / 3 Bathrooms / Sleeps 14
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    • Private Fishing...
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    • Waterfront
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    • x
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    About this property
    Historic summer 'cottage' with 7 bedrooms, sleeping porches, a deck overlooking the water, a private dock on Harthaven Harbor, and immediate access to the ocean. The rustic home is a perfect gathering spot for family and friends. It has a large living room with a huge stone fireplace, an eat-in... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    About this property
    Beachfront living combined with the convenenience of in-town. This condo makes your Vineyard vacation easy. Enjoy sweeping ocean views of Nantucket Sound and Chappaquiddick, with Oak Bluffs' popular Inkwell Beach directly across the street. Enjoy a second floor condo with water views from the... View all property information
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    3 Bedrooms / Sleeps 8
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    About this property
    Nicely decorated 3 bedroom 2.5 bathroom Colonial home located in a private setting in Oak Bluffs. Upon entering the quiet street there is plenty of room for two plus vehicles to park, a large back deck for entertaining and ample yard space for a game of catch or Frisbee. Inside your will find... View all property information
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    3 Bedrooms / 3 Bathrooms / Sleeps 7
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    • x
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    • x
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    About this property
    Newly renovated and painted campground victorian home with gingerbread accents. This charming victorian is ideally located close to town, shops, restaurants and beaches. Enjoy peeks of the harbor while watching the sunset from the new roof top deck. Additional amenities include: coffee maker,... View all property information
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    5 Bedrooms / 2 Bathrooms / Sleeps 10
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    • x
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    About this property
    This grand ginger bread cottage recently updated, offers lots of living space on 2 levels, with a kitchen, living room and full bath on each level. Perfect for extended families looking to spend vacation time together while enjoying expansive living space on two levels. The access stairs to the 2nd... View all property information
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    5 Bedrooms / 2 Bathrooms / Sleeps 11
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    About this property
    Privately situated on a hilltop in Sengkontacket, -spacious tri-level contemporary home. This wonderful vacation home has been updated for summer 2015, AC added, freshly painted, new carpeting and hardwood flooring and new furnishings. Set in a wonderful family friendly community offering... View all property information
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    1 Bedroom / Sleeps 4
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    • Waterfront
    • Water Views
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    About this property
    Martha's Vineyard contemporary cozy one bedroom guest house has an open floor plan with a light and airy feel to it.It is extremely clean and well cared for. It offers a private get away yet easy access to 150 feet of private Oak Bluffs beach on the Lagoon waterfront. This is shared with the Main... View all property information
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    1 / 31
    6 Bedrooms / 2 Bathrooms / Sleeps 11
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    • Air Conditioning
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    • Pets allowed
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    • Suitable for children
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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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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    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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    5 Bedrooms / 6 Bathrooms / Sleeps 10
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    About this property
    Bright, open totally redesigned, restored and expanded summer cottage on a quiet street in an historic and lovely neighborhood. Less than 1/2 mile from town. Open space plan for maximum interaction for everyday or special gatherings. Private nooks for book reading. Numerous large windows throughout... View all property information
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    5 Bedrooms / 4 Bathrooms / Sleeps 13
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    About this property
    This newly renovated Oak Bluffs home offers a spacious interior, with plenty of nooks for all to have their own space. A spacious deck and yard are perfect for entertaining and cookouts. The attic offers a wide open floor plan which is perfect for kids to get away from mom and dad. This home offers... View all property information
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    5 Bedrooms / 2 Bathrooms / Sleeps 9
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    About this property
    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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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    This four bedroom two plus bath home is located in Meadow View farm with access to association tennis, bike path and Farm Neck Golf close by. This lovely home offers a comfortable living room, up-dated kitchen, formal dining room and a screened-in porch all tastefully decorated and freshly painted.... View all property information
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    1 / 9
    5 Bedrooms / 2 Bathrooms / Sleeps 9
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    • Air Conditioning
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    About this property
    Across the street from the renowned Inkwell beach and just minutes to walk to town, harbor and the ferry. This large classic victorian beach house was built in 1851. The property has a beach studio next door which can be rented for larger groups. A large classic wrap around porch with ocean... View all property information
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    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    About this property
    Spacious contemporary 4 bedroom 3.5 bath home located in one Oak Bluffs most exclusive neighborhoods. This house offers many features such as hardwood floors, central air conditioning, and a large living dining area with walk out deck and patio. The yard is nicely landscaped with waterviews over... View all property information
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    About this property
    Wonderful, spacious, lovingly maintained and attractive home in exclusive setting - family room with fireplace, large formal living room with fireplace, master bedroom with full private bath. Large kitchen and dining area that opens onto wonderful deck. Association tennis and boat landing on... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Watch the boats come and go from the harbor while you picnic and relax on your beach. This fabulous waterfront three bedroom main house and three bedroom guest house also offers your own dock and mooring. Additional amenities include: beach chairs, dock/boat-slip, coffee maker, bakeware, outdoor... View all property information
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    4 Bedrooms / 3 Bathrooms / Sleeps 9
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    About this property
    OAK BLUFFS, We purchased our dream home in the fall of 2011 and we have finished a complete renovation of our circa 1900 Oak Bluffs cottage. When we walked into the house we knew we wanted to restore this beautiful old family summer home. New meets old throughout the house; state of the art... View all property information
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    4 Bedrooms / Sleeps 8
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    About this property
    Great Martha's Vineyard four bedroom beach house situated across the street from a Park. With four bedrooms and 3.5 baths, this property is located within an easy walk to town, ferry, and Oak Bluffs town beach. Additional amenities include: outdoor shower: enclosed, beach access: public, flipkey... View all property information
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    3 Bedrooms / 1 Bathroom / Sleeps 7
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    About this property
    The Mermaid Boathouse is designer renovated waterfront cottage that has been transformed into a terrific year round home. Located East Chop, situated on a peaceful, private setting 1 mile from downtown Oak Bluffs. A quaint cottage experience with all the amenities of a four star hotel. Relax in... View all property information
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    OAK BLUFFS: The Highlands. Less than one mile to town. Immaculate, comfortable and family friendly.First floor; living room, dining area, kitchen, queen bedroomm twin bedroom and bath. Second floor has twin bedroom and full bedroom and a second bath. DSL internet connection. Departure cleaning... View all property information
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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    You are just steps from Circuit Avenue, Oak Bluffs Harbor and the beach from this comfortable in-town apartment in an exclusive small building. The sun-filled great room has open living and dining areas, and a well-equipped kitchen. The two bedrooms are also on the main floor. Stairs lead up to a... View all property information
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Satellite TV
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    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This home offers a spacious open floor plan providing a comfortable yet elegant retreat, truly an upscale surprise, perfect for relaxing or entertaining. With an expansive mahogany wraparound deck, sweeping views and a screened-in porch, enjoying the evening sunsets while grilling and dining al... View all property information
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    3 Bedrooms / Sleeps 8
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    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Three bedroom Colonial located in prestigious Meadow View Farms. Property offers granite counter-tops with stainless steel appliances, hardwood floors throughout, flat panel TV in kitchen/dining and loft space. Large screened in porch with deck with plenty of outdoor space for any outdoor game.... View all property information
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    $544
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    NEW FOR THE 2015 SEASON! BETTER PICTURES FORTHCOMING - HOUSE WILL HAVE ALL NEW FURNISHINGS AND FRESHLY PAINTED TO GIVE IT THAT VINEYARD BEACHY FEEL! PLEASE INQUIRE FOR MORE INFORMATION. Views, Views and more Views! Lovely water views of Sengekontacket Pond over the rolling 'forever' conservation... View all property information
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    $2,156
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    6 Bedrooms / 2 Bathrooms / Sleeps 11
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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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    5 Bedrooms / 2 Bathrooms / Sleeps 8
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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
    East Chop Victorian home. Newly renovated in 2011. Walk to the Bluff and enjoy panoramic ocean views. Bike to the public beach by the beach club or into town and the large public beach beyond. Large flat screen TV in living area and wireless internet for your convenience. There is also a smaller TV... View all property information
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    $2,219
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
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    • Elder access
    • ?
    • ?
    About this property
    Outrageous views from this third floor condo #304) overlooking the beach in Oak Bluffs. Walk to Circuit Avenue for all the happenings in town. Well equipped and nicely decorated, this is a great get-away venue. Elevator, parking, convenience. Additional amenities include: beach chairs, sofabed,... View all property information
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    $3,360
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Dishwasher
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    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Please note - all new master bedroom and bath completed in 2014 (not shown in photos) Amenities and Features include... Sengekontacket, Central Air Additional amenities include: coffee maker, patio table and chairs, lobster pot, food processor, washer / dryer, cd player, landscaped, outside... View all property information
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    $6,340
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    1 / 25
    3 Bedrooms / Sleeps 8
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    • Air Conditioning
    • Dishwasher
    • Internet Access
    • Satellite TV
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    View the waters of Lagoon Pond from various rooms in this pristine Oak Bluffs waterfront property. Tastefully decorated. There are three bedrooms on the second floor all en suite and two more sleeping areas on the first floor that can be used for extra guests. One has a queen sofa bed and the other... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
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    • Elder access
    • ?
    • ?
    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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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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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    7 Bedrooms / 4 Bathrooms / Sleeps 10
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    • Air Conditioning
    • Dishwasher
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    • Internet Access
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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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    8 Bedrooms / Sleeps 16
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    EAST CHOP! This Victorian Martha's Vineyard cottage is in one of the best locations Oak Bluff's has to offer. It is close to beach, shops, and restaurants giving you and your guests great versatility. A truly classic Vineyard summer house with numerous bedrooms, plenty of living space and large... View all property information
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    $1,395
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • 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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    1 Bedroom / Sleeps 2
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    • Air Conditioning
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    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Downtown Oak Bluffs! Be right in the center of all the action on Church's Pier on Oak Bluffs Harbor. Great proximity to harbor, Circuit Avenue, Steamship Authority, Fisherman's Pier and miles of sandy beach! No need to bring a car, just a block from the Oak Bluffs ferry and great island wide... View all property information
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    $634
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    4 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    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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