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Cottages and House Rentals in Oak Bluffs, MA

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    Travelers to Oak Bluffs are booking June dates now. Secure your vacation 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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    1 / 17
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 1 Bathroom, Sleeps 8 | 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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    About this property
    Our comfortable, reverse contemporary home has 2 bedrooms on the first floor (one with a full size bed and one with a twin), a 3/4 bath with shower, as well as a family room with a fold-out futon couch. Upstairs on the second floor, our home has an open design with a bright kitchen/dining/living... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    4 of 5 bubbles Reviewed August 25, 2016
    My stay at the house was very good and the photos were true to the accommodations. I thought there were 2 twin beds in one of the rooms but it was ok since the downstairs den had...
    5 of 5 bubbles Reviewed April 13, 2016
    Location, location is perfect for getting to town, beach and other parts of MV! The house is right size for family of 4. The owner is very responsive and the house was well...
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    1 / 9
    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
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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
    1 / 44
    2 of 5 bubbles (1) Poor
    6 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    <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
    1 / 28
    4 Bedrooms, 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
    1 / 17
    5 of 5 bubbles (2) Excellent
    6 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Ocean Views
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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
    1 / 14
    5 of 5 bubbles (3) Excellent
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Classic & charming, turn of the century 'campground' home situated on a 4,400 sq. ft. corner lot just a few minutes walk from the beach & town. Spacious & light rooms w/ some intimate spaces, a formal dining room, hardwood & pine floors, and a sweet porch all blend into a wonderful vacation spot.... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    1 / 12
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    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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    Oak Bluffs, Martha's Vineyard
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Stylish Cape located close to town and beach.attention to detail in every room. Relax and enjoy all the comforts of home in this all new pristine 3 bedroom, 2 bath home. The main living level features an open kitchen living and dining with AC. In additon there is separate TV room with office area... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 7
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Amenities and Features include... Walk to Town and Beach, Newly Renovated Additional amenities include: coffee maker, patio table and chairs, lobster pot, washer / dryer, landscaped, outdoor furniture, ironing board. View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 12
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    Lovely contemporary home in one of the Islands premier community settings, Waterview Farms. Close to Farm Neck Golf Course and tennis and a short distance to town and beaches. Amenities and Features include... Waterview Farms, Waterview Additional amenities include: dock/boat-slip, coffee... 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 / 17
    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    Great Four Bedroom Home in Meadow View Farms Additional amenities include: coffee maker, tennis, outdoor shower, lobster pot, wine glasses, washer & dryer, ironing board. View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 30
    4 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    • Balcony
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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
    1 / 22
    7 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    Classic, "Camp Ground" over sized 7 bedroom 3 bath home in a residential neighborhood within easy walking distance to the beach, shops, restaurants, galleries, etc. It offers double master bedrooms (1st and 2nd floor.) Enjoy rocking on our huge front porch in over sized Georgia rockers. As you... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 21
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
    1 / 35
    5 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    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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    1 / 11
    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
    1 / 11
    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 / 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 / 23
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Newly refurbished, stately 4262 sq ft. home with 4 bedrooms, 2.5 baths situated within a five minute walk to the center of Oak Bluffs, beaches, and ride/jog to bike trail. Large fenced yard with shared tennis court and patio. Spacious, open 35x45 living room downstairs with smaller living room,... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 15
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
    5 Bedrooms, 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
    1 / 25
    2 Bedrooms, 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 / 16
    3 of 5 bubbles (2) Average
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Terrace
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    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 / 18
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    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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    Oak Bluffs, Martha's Vineyard 02539
    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
    1 / 13
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Amenities and Features include... In-Town, WiFi Additional amenities include: coffee maker, patio table and chairs, fans - portable, lobster pot, washer / dryer, cd player, landscaped, outside shower - enclosed, outdoor furniture, ironing board. View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 10
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    This sweet, little (it's priced accordingly!)cottage is all about convenience. It is within walking distance to the center of Oak Bluffs and two town beaches. The interior of the cottage has recently been redone inside and is fresh & clean and perfect for a great vacation. Large decks, lovely... View all property information
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    Oak Bluffs, Martha's Vineyard 02539
    1 / 16
    5 of 5 bubbles (3) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    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 / 20
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Leave your worries and your car behind, this picture perfect Vineyard beach house is steps from downtown Oak Bluffs, the sandy beach and a few short blocks from the ferry. Recently renovated and restored, four-bedrooms and one and a half baths, offering the perfect juxtaposition of cottage charm... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Spectacular water view in desirable East Chop neighborhood. This 4 bedroom, 3 bath home is just 1.5 miles from Oak Bluffs Center and Beach. There is a yard with multiple decks and waterviews. Features include central air and wifi internet. Beautifully decorated. Amenities and Features include...... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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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    Oak Bluffs, Martha's Vineyard
    1 / 14
    4 of 5 bubbles (1) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Come experience the magic of the Vineyard in our island home. Modernized in 2011, this charming residence is clean, cozy and boasts new furniture and decor. Amenities include 3 TV’s, cable television, Wi-fi, DVD, telephone, I-home, and Keurig Coffee maker. The property has a private yard, sundeck,... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 21
    4 of 5 bubbles (1) Very good
    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    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
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Grill
    • Satellite TV
    • Wi-Fi
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
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    5 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • Patio
    • DVD Player
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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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    Oak Bluffs, Martha's Vineyard 02539
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    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • DVD Player
    • Grill
    • Internet Access
    • Satellite TV
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • 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
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
    • Satellite TV
    • Patio
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    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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    8 Bedrooms, 8 Bathrooms, Sleeps 20 | Quick View
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    • Hot Tub
    • Grill
    • Patio
    • DVD Player
    • Terrace
    • Washer
    • Balcony
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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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    Oak Bluffs, Martha's Vineyard 02539
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    4 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • Satellite TV
    • Internet Access
    • DVD Player
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This whimsical summer home located in Water View Farms, provides a peaceful retreat overlooking wild flower meadows. Launch canoes or kayaks from the private association beach on Sengekontacket Pond, just a short walk from the house. Great waterfront play area for young children at the association... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 19
    7 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Come and relax on the front porch of this lovely Vineyard home. Located in the desirable East Chop area of Oak Bluffs. The first floor has a nice open space with dining area and living room. There is a nice kitchen with everything you need to make family dinners. There is a bedroom and full... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Central Heating
    • Internet Access
    • Grill
    • Parking
    • Washer
    • Satellite TV
    • DVD Player
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    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
    Location Information
    Oak Bluffs, Martha's Vineyard 02568
    1 / 15
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Grill
    • Porch
    • Wi-Fi
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Enjoy beautiful water views 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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    Oak Bluffs, Martha's Vineyard 02557
    1 / 23
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • DVD Player
    • Patio
    • Shared Outdoor Pool...
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
    1 / 19
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Wi-Fi
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Oak Bluffs, Martha's Vineyard 02539
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