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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 stars (2) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    1 / 18
    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 16
    3 of 5 stars (2) Average
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 17
    5 of 5 stars (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
    Location Information
    Oak Bluffs, Martha's Vineyard 02557
    5 of 5 stars 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 / 20
    5 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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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: nearby bank, close... View all property information
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    Oak Bluffs, Martha's Vineyard 02539
    1 / 44
    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 / 22
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    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 / 61
    5 Bedrooms, 4 Bathrooms, Sleeps 22 | Quick View
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    • Hot Tub
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    About this property
    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
    1 / 13
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Our picture-perfect home is an excellent summer escape. Spacious double lot makes this setting seem like a parkland. It's just a 15-minute walk to downtown Oak Bluffs and the town beach. It's also on the public transit line and the bike path. View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 26
    4 of 5 stars (1) Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 13 | Quick View
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    About this property
    Newly renovated 5 bedroom home just a mile and a half from the center of Oak Bluffs. New hard wood floors throughout as well as updated furnishings and decor. Dining area is extended by a nice sized sunny deck for outdoor dining. Perfect for a large family vacation. Additional amenities include:... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02557
    4 of 5 stars Reviewed 11 August 2013
    Nice, clean, updated home with space for everyone. We divided older teen girls in upstairs dorm style rooms that slept 5 from you get boys and girls in two rooms that slept 2 and...
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    1 / 9
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
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    • Secure Parking
    • Balcony
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    • Ocean Views
    • Terrace
    • Private Garden
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    About this property
    This is an original Pratt house built in 1866 by the famed architect Pratt for whom the Pratt Institute in New York was named. It is located in the historic district across from a large park in which baseball, golf practice, kite flying, bike riding, picnics and even, on at least one occasion,... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 22
    4 of 5 stars (1) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Walk to town from this meticulously maintained, large & airy, 3 bedroom, 3 full bathroom vacation getaway, located on a beautiful 1/4 acre lot on a quiet street. Watch your troubles sail away while relaxing on the large farmer's porch with your favorite summer beverage, or grilling with family and... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 43
    6 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • x
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    About this property
    The Weku House is a luxury, 5,000 square foot home located in the beautiful town of Oak Bluffs on Martha’s Vineyard. Originally built in the year 2000, this home was fully renovated in 2015. Elegantly decorated with designer furnishings and interior appointments, the meticulous attention-to-detail... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 22
    4 of 5 stars (2) Very good
    8 Bedrooms, 3 Bathrooms, Sleeps 16 | Quick View
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    About this property
    A true Vineyard classic from 1890, this house retains its authentic charm yet has been thoughtfully renovated and serves the modern day vacationer well. The 8 bedrooms afford plenty of space to accomodate larger family groups for special reunions and vacations. The living room, sunporch and kitchen... 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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    • x
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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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    Oak Bluffs, Martha's Vineyard 02539
    1 / 21
    4 of 5 stars (1) Very good
    6 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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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 / 15
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    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 / 27
    6 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Grill
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    • x
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    About this property
    Seaside Cottage Style Vacation Home. Recently renovated. Perfect for extended families. Walk to Oak Bluffs town center, beach across the street and miles of beach side - bike paths begin just a couple of hundred yards from the house. Ocean views from just about all rooms. Wonderful, large summer... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 30
    7 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    About this property
    In Town, walk to beach, tennis and town area. This wonderful family home has a large wrap around porch, 7 bedrooms and sleeps 12-14. Many areas of this wonderful older home have been updated. Hi Speed Internet. Amenities and Features include... 1 Block to Beach, Wifi Internet, Linens Provided,... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • x
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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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    1 / 19
    7 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    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
    1 / 23
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    • x
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    About this property
    Amenities and Features include... Hidden Cove, Centrally Located to Beaches and Towns, Association Tennis Courts, A/C, WiFi Additional amenities include: coffee maker, patio table and chairs, fans - portable, lobster pot, washer / dryer, landscaped, outside shower - enclosed, vacuum, outdoor... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 38
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • x
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    • x
    About this property
    Sea breezes and fabulous water views from almost every room are the mainstay for this unique waterfront home on the Lagoon Pond in Oak Bluffs. Polished with soothing designer furnishings in layers of cappuccino and white neutral linen and cotton, you will enjoy this European-chic interior almost as... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 28
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Porch
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    • x
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    About this property
    Extended families are sure to enjoy this Tri-level home featuring open floor plan on the main level, large main living room and two den TV areas one on the first level one and an additional TV area on the 2nd level. Kitchen has stainless appliance and granite counters and the family dining area is... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 23
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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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
    1 / 9
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    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 / 15
    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Waterfront
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    About this property
    Large families looking for a beachfront adventure will love this relaxed waterfront home. Spectacular views from every room and expansive patios stretch the shoreline. Central location offers a 5 minute drive to town, dining, movies, shops and galleries. Amenities and Features include...... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 16
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    Amenities and Features include... Central Air, Additional amenities include: coffee maker, lobster pot, food processor, 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 / 37
    7 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • Waterfront
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    • x
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    • x
    About this property
    Large families looking for a true shore experience will enjoy this delightful,whimsical, large historic summer home with cottage details set on the edge of Harthaven Harbor. The home boasts spectacular views of Vineyard Sound from all areas of the home. Private path leads you to a pristine private... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 13
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    This contemporary Cape, in a private setting, features a spacious, open, light, airy design with a wonderful large wrap-around deck. The bike path and MVTA (bus) are just a short ride/walk from the house. Two association tennis courts are an added plus! Additional amenities include: coffee maker,... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 34
    5 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • x
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    • x
    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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    Oak Bluffs, Martha's Vineyard
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    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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    Oak Bluffs, Martha's Vineyard
    1 / 23
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    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
    1 / 9
    4 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    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 / 15
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Crisp, elegant and tastefully decorated. This lovely 2 bedroom, 2 bath condo is across the street from the beach and a 5 minute waterfront walk to town, ferry, movies, galleries, dining and entertainment. Enjoy the spectacular views from your balcony or cross the street for a morning swim. Great... View all property information
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    Oak Bluffs, Martha's Vineyard
    5 of 5 stars Reviewed 27 August 2014
    ...second floor 2 bed room 2 bath condo with balcony that overlooks Inkwell Beach in Oak Bluffs on Martha"s Vineyard...great walkable location to Oak Bluff's Circuit Avenue for...
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    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Lovely two bedroom, 2 bath condo unit with sweeping water views. Town center is but a 5 minute walk from the condo complex where you will find, family and fine dining, shops. groceries, the famous Flying Horse Carousel,- a great attraction for children and the young at heart. Stroll along the... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 25
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Gorgeous Meadow View Farms home bordered by expansive landscaped yard, Association tennis courts just a short distance from the house and Farm Neck Golf and Tennis is just a half mile from the house.Connecting bike paths begin at the entrance to Meadow View. This sun filled contemporary home... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 12
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
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    • x
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    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
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    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Grill
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    • Pet-friendly
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    • x
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    • Smoking allowed
    • x
    About this property
    The Blue Canoe is completely fresh and renovated, while its 1910 charm is fully intact. It has a lovely deck and a huge side yard surrounded by a split rail fence just perfect for enjoying summer lounging and games. The house is in a neighborhood central to many things including being just steps to... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02557
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    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    • Pet-friendly
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    • x
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    • 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 / 33
    5 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • Private Outdoor...
    • DVD Player
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    • Pet-friendly
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    • x
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    • Smoking allowed
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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
    Location Information
    Oak Bluffs, Martha's Vineyard
    1 / 23
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Patio
    • Satellite TV
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Views, Views and more Views! Lovely water views of Sengekontacket Pond over the rolling "forever" conservation land. Large contemporary home has been recently updated to 4 bedrooms and 3 full baths. Large open living space with deck overlooking the view and sun room. Access to association dock and... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02539
    1 / 23
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    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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    Oak Bluffs, Martha's Vineyard
    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    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 / 20
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    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
    1 / 22
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    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
    1 / 18
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    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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    Oak Bluffs, Martha's Vineyard
    1 / 21
    5 of 5 stars (2) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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 stars 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 stars 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 / 27
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Patio
    • Satellite TV
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    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
    Location Information
    Oak Bluffs, Martha's Vineyard
    1 / 21
    5 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Satellite TV
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Beautiful luxury home overlooking Farm Neck 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. Expansive gourmet kitchen with dining area is great for family gatherings after the beach.... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02557