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Holiday Homes and Apartments Oak Bluffs, MA

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    Travellers to Oak Bluffs are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 17
    4.5 of 5 bubbles (2) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    5 of 5 bubbles (3) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    4.5 of 5 bubbles (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Beautiful and spacious 3 bedroom in Oak Bluffs, Martha's Vineyard. Sunny, open and airy Cape. Walking distance to town, gingerbread cottages, library, and playground. Close to beach, golf course, and great fishing spots. There is a pack and play in the upstairs bedroom for a baby to sleep or nap... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 17
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    About this property
    This is an old farmhouse consisting of 2 floors with 3 bedrooms on the second floor and 1 on the first floor. One queen and 3 doubles. A large living room and bath on the first floor. In the kitchen is a Refrigerator, gas stove with oven, a washer and dryer and a dishwasher. There is a portable... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    5 of 5 bubbles Reviewed 23 August 2014
    So often descriptions fall short of reality but our stay at this Flip-key rental was as it was toted, a "Charming Farmhouse." The four bedrooms were sweet and spacious decorated...
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    1 / 44
    2 of 5 bubbles (1) Poor
    6 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    <BR>*Fall/Winter/Spring multi-week discount available<BR><BR>*Only 3 prime summer weeks left! Check my calendar and book ASAP if you plan to visit in the peak season.<BR><BR>The Pennacook house in Oak Bluffs on the charming island of Martha's Vineyard is beautifully maintained, bright and sunny,... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    European-styled cottage is tucked away down a private lane surrounded by private yard with gardens - you’ll feel like you have completely gotten away from it all. The front door opens into a classic Mudroom with an antique wood, stadium bench seat - and then you step into the open and airy Great... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Home away from Home! Walk to Sailing Camp! Bright, sunny 3 bedroom Cape style vacation home in Lagoon Heights with great amenities. Fully furnished home with 2 baths, outdoor shower, large deck and private enclosed yard and a wonderful deck for the summer cookouts. Open floor plan with spacious... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    Summer Dream offers the opportunity for a relaxing vacation in a beautiful environment. This 4 bedroom, 2 ½ bath home has a beautiful new kitchen and new living room furnishings including a 56' LED television. Summer Dream is in the lovely Hidden Cove neighborhood adjacent to Sengekontacket Pond... View all property information
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    Oak Bluffs, Martha's Vineyard
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    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    Come and let your cares float away as you relax on the enormous first-floor front porch or second-floor open deck of this charming 100+-year-old home looking out onto the beautiful Nantucket Sound. The home is sunny, bright and spacious and has a relaxed elegance with a large open living room... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    1 / 20
    8 Bedrooms, 8 Bathrooms, Sleeps 20 | Quick View
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    • Hot Tub
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    About this property
    Amazing five acre property! 6 BR main house w/ pool + a 2 BR carriage house! Our amazing property is perfect for everything from a memorable family vacation to a serene retreat. You and your guests will begin to enjoy the feeling of privacy the minute you arrive as you drive down the long tree... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 31
    Studio, 3 Bathrooms, Sleeps 7 | Quick View
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    Architect designed, luxury waterfront retreat. This unique home sits overlooking 500 feet of private lagoon beach and maintains sweeping waterviews up the lagoon. The pool and patio areas feature outdoor dining, sectional sofa seating, lounge area, and a hot tub all taking full advantage of the... View all property information
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    Oak Bluffs, Martha's Vineyard
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    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    If you are looking for an immaculate, charming, cottage style, yet modern home and close to Oak Bluffs center look no further. This recently updated 3 bedroom, 2 bath home features sunny open living, kitchen and dining areas. Soft seashore color palette throughout adds to the ambiance of this great... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 22
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Just a block from the East Chop Bluffs on a sleepy side street in a quiet wooded setting. There are 2 SEPERATE LIVING ROOMS!! Large bright kitchen that accesses a separate dining room, inviting screen porch with dining and sitting areas, and sunny rear deck with lots of backyard privacy. Ocean... View all property information
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    Oak Bluffs, Martha's Vineyard 02257
    1 / 7
    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    About this property
    A comfortable ranch with all the amenities for a perfect vacation. It's quiet location is 1.5 miles from town, yet not too far to bike or walk in when needed. Beaches, ponds, the lagoon, and other recreational facilities are also easily accessible if you want to hop on the bike path around the... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 61
    5 of 5 bubbles (1) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 22 | Quick View
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    This upscale, newly renovated, 4 bedroom home in a quiet neighborhood in Oak Bluffs. You are 2.5 miles from the town center and Inkwell and State beautiful public beaches. This home boasts a large unground back yard pool and hot tub on the mahogany deck. Large outdoor shower. Grill and fire pit... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    Studio, 2 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Privately situated on a hilltop in Sengkontacket, -spacious tri-leve 4000 sq ft 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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    Oak Bluffs, Martha's Vineyard
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    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Stay in this peaceful, well-maintained home with a large wrap-around porch, a deck, and in close proximity to the ocean for your next unforgettable New England vacation. Come with a small group of friends, bring your own small family, or get away with another couple and rest assured that you'll... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 22
    Studio, 3 Bathrooms, Sleeps 7 | Quick View
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    About this property
    New for the 2016 season! Enjoy this wonderful new three bedroom three and half bath home in Oak Bluffs. The first floor has an open concept with a beautiful chefs kitchen, large dining room and family room with TV. The first floor also has a master bedroom en suite with a king size bed and TV.... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 17
    5 of 5 bubbles (2) Excellent
    6 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Waterview - located on the East Chop Vineyard Highlands overlooking Nantucket Sound, Oak Bluffs harbor, Sunset Lake, and 3 acre Washington Park, this charmingly original 1860's Vineyard cottage is an ideal family vacation home. Leave the car on the mainland or in the driveway, for everything,... View all property information
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    Oak Bluffs, Martha's Vineyard 02568
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    1 / 27
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    MVVR EXCLUSIVE: Custom crafted tri-level, this beautiful sun filled home features, spacious open living spaces, hardwood floors throughout, sleeps 8 with 2 King Masters en-suite, guest king bedroom and semi-private Alcove sleeping area on the 2nd level ( see photo 23) Exterior features include two... View all property information
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    Oak Bluffs, Martha's Vineyard
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    Studio, 3 Bathrooms, Sleeps 12 | Quick View
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    Charming six bedroom home located within walking distance to town. The first floor has a nice living room/dining area with doors that open to the front porch. There are two bedroom and one full bath on the first floor too. The second floor has four additional bedrooms and two bathrooms. There... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    Studio, 4 Bathrooms, Sleeps 8 | Quick View
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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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    Oak Bluffs, Martha's Vineyard 02539
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    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This charming home is situated in an idyllic private wooded setting on Sengekontacket Pond, one of the largest salt-water ponds on Martha's Vineyard. Comfortably furnished, it has a newlyr renovated kitchen and a new dining area overlooking Major's Cove. There is also a new screened in sun room for... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 30
    5 of 5 bubbles (1) Excellent
    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Located on over 1 acre of waterfront property on East Chop, an exclusive area of historic Oak Bluffs, this unique home is perfect for family and friends that want to vacation together while maintaining their privacy. This home allows up to 4 families to stay together in the same home while giving... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 18
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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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    Oak Bluffs, Martha's Vineyard 02557
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    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    Cute and Cozy guest house with open floor plan in the kitchen, living and alcove sleeping area with queen bed. This cottage is perfect for couples, the owner will consider one additional child. There is a den with futon sofa separate from the main part of the cottage. Relax on the deck while you... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 21
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Sea Glass Cottage Martha's Vineyard Vacation Rentals Sleeps 6. Completely renovated, this charming East Chop cottage will allow its guests to experience all the comforts of modern luxury living combined with the historical splendor of many reclaimed antique furniture pieces from Martha's Vineyard... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    4 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    New Renovated, 1870 historic "Campground" cottage centrally located in Oak Bluffs, The cottage has 4 bedrooms (all located on the second floor) - 1 queen, 2 double beds and 2 twins beds. The front bedroom has its own balcony with water views. Cottage sleeps 8. the first floor includes a newly... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    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 lovely views of the the lagoon. The master... View all property information
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    Oak Bluffs, Martha's Vineyard
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Completely renovated cottage in the Sunset Lake area of Oak Bluffs. Walk to town and library. Completely renovated modern kitchen. Rock away on the large front porch. Additional amenities include: games, coffee maker, outdoor shower, lobster pot, cd player, wine glasses, fans, vacuum, washer &... View all property information
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    Oak Bluffs, Martha's Vineyard 02539
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    Studio, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    Come and enjoy the newly renovated two bedroom home in Oak Bluffs. The first floor which is done in bright coastal colors has a nice eat in kitchen with a couple steps up to the living room with a large flat screen TV. The first floor also have a half bath. The second floor has two bedrooms and... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    Studio, 4 Bathrooms, Sleeps 8 | Quick View
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    Beautiful waterfront home with central A/C, features open floor plan and sunny living spaces. The great room has two distinct seating areas and is equipped with a flat screen TV. There is a formal dining room set between the living area and kitchen and opens to the outdoor patio with gorgeous... View all property information
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    Oak Bluffs, Martha's Vineyard
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    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    This 4 bedroom home with skylights, 52 inch Tv, computer, internet, printer, fax, is your home away from home. 1 mile from town 1.5 mile from beach and 7 miles from airport is ideal location. 2 SETS OF GOLF CLUBS AND 4 TENNIS RACQUETS FOR YOUR USE, 3 CABLE TV'S, MASTER BATH HAS WHIRLPOOL TUB... View all property information
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    Oak Bluffs, Martha's Vineyard 02568
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    4 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    New to the 2015 Summer Season! This spacious waterfront home offers 4-bedrooms en-suite, with family, game and fitness rooms...and yes, a pool. The peaceful setting is centrally located, yet close to the village center for easy access to shops, restaurants and more. The home is tastefully... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    MVVR EXCLUSIVE: Adorable, pristine beach cottage has spectacular views across the sound, calm water swimming, great area for kayaking. The open kitchen, dining and living areas are enhanced by the wall of windows facing the waterfront and providing gorgeous water views . Enjoy the parade of... View all property information
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    Oak Bluffs, Martha's Vineyard
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    Studio, 4 Bathrooms, Sleeps 12 | Quick View
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    Sitting on the "summer porch" (that is what they were called in the days of old) sipping your favorite beverage, strolling the short distant to the water, relaxing around the table, Well equipped kitchen, reading in the living room with your feet these are possible when you stay in this well cared... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    A new Cape style residence situated on a wooded lot near bike path and just a short ride to town center and ferry. This home features an open design with a bright kitchen/dining/living area with hardwood floors, den and full bath on the first floor. Sliders in the dining area lead out onto a nice... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 21
    5 of 5 bubbles (2) Excellent
    Studio, 2 Bathrooms, Sleeps 7 | Quick View
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    • Air Conditioning
    • Grill
    • Satellite TV
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    • Pet-friendly
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    About this property
    Delightful summer cottage. Great family home for relaxing on the large deck, kayaking the lagoon, great play beach on the lagoon for children. The bunk house with two bedrooms is directly behind the main part of the house, about 10 steps across the yard. The views are spectacular and expansive.... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    5 of 5 bubbles Reviewed 25 July 2014
    The house was perfect for our family. The views from the deck, family room and bedrooms were incredible. We ended up grilling 4 out of the 7 nights we were there because there is...
    5 of 5 bubbles Reviewed 18 July 2014
    I would love to say it was an awful stay so no one else would want to stay there but us, but truth be told - it was GLORIOUS. We so enjoyed sitting on the deck in the morning...
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    1 / 18
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Pet-friendly
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    • x
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    • x
    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
    Location Information
    Oak Bluffs, Martha's Vineyard 02539
    1 / 18
    Studio, 2 Bathrooms, Sleeps 7 | Quick View
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    • Satellite TV
    • Air Conditioning
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Classic vineyard cottage renovated, tastefully and comfortably furnished. Large open deck on both the main and 2nd levels. Main living level features a lovely kitchen very well stocked with dining and cook items, a large sunporch living area and 2nd living area with large screen TV. Three lovely... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 16
    3 of 5 bubbles (2) Average
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
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    Amenities & Details
    • Terrace
    • Balcony
    • Satellite TV
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Private Garden
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Adorable GINGER BREAD house in Oak Bluffs that I rent out for 6 weeks each summer. Best location! It's a 2 minute walk to the harbor, town restaurants, shops and bars. The OCEAN is a 6 minute walk! House is adorable, furnished, AC in some rooms, parking. Overlooking a park, sip your coffee on the... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 15
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    • x
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    • Smoking allowed
    • x
    About this property
    Waterview Farm boasts views across peaceful meadows to Sengekontacket Pond and beyond. Launch canoes and kayaks at private association beach on the pond. Great location for families. Close to bike paths, town and beaches. House has an open, airy floor plan and large deck. Amenities and Features... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 15
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Internet Access
    • Grill
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    All newly remodeled and furnished and tucked away on a quiet Oak Bluffs lane for the perfect reprieve after a day at the beach and shopping in town, along the Oak Bluffs harbor - and all just a short drive or bike ride away. This vacation home looks and feels so comfortable when you first walk in.... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 16
    5 of 5 bubbles (3) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
    • Grill
    • DVD Player
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Wonderful home located about a 10 minute walk to downtown Oak Bluffs. This home has a nice open floor plan for family gatherings, updated furnishings, fully equipped kitchen with stainless steel appliances, Master bath Jacuzzi tub, Entertainment systems include flat screen TVs, CD, DVD, VCR,... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 21
    4 of 5 bubbles (1) Very good
    Studio, 3 Bathrooms, Sleeps 12 | Quick View
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    • Air Conditioning
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    • Pet-friendly
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    • x
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    • x
    About this property
    This well maintained, vintage Victorian home is centrally located, yet away from the hustle and bustle of town: just one block from the beach, two blocks from Waban Park and Ocean Park, three blocks from tennis, backetball and a playground and four blocks from town. Enjoy the waterview of Vineyard... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 26
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    Amenities & Details
    • Washer
    • Satellite TV
    • DVD Player
    • Ocean Views
    • Air Conditioning
    • Housekeeping...
    • Patio
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This fabulous 125 year-old Victorian cottage was lovingly updated and completely restored in 2012. Sitting on a large private lot, just steps from Inkwell beach, Solera offers the perfect balance of comfort, ambiance and vintage charm. The large, airy gourmet kitchen was featured in This Old House... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 19
    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    • DVD Player
    • Grill
    • Internet Access
    • Satellite TV
    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Tiny beach cottage, a rare find these days and just perfectly cute. The cottage is located along the waterfront on East Chop Drive, a very desirable area of Oak Bluffs. The porch looks out over the beach and beyond to the Vineyard Sound. Relax on the covered porch and take in the outstanding... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 12
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
    • DVD Player
    • Satellite TV
    • Grill
    • Internet Access
    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    This cozy, quaint waterfront property offers beautiful sunsets and great harbor views. Swimming, boating, kayaking, are just steps from this warm and charming quintessential Vineyard cottage. Amenities and Features include... Waterfront, Waterview Additional amenities include: dock/boat-slip,... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 22
    Studio, 3 Bathrooms, Sleeps 13 | Quick View
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    • Grill
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This outstanding Oak Bluffs home is undergoing a complete face lift for the 2012 rental season and is sure to please. Spacious and perfect for extended families, featuring multiple attractively furnished living areas and sleeping 13 comfortably. The lower level of the house features a queen bed,... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard