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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 / 9
    Studio, 1 Bathroom, Sleeps 8 | Quick View
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    5 of 5 bubbles (2) Excellent
    6 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This charming Cape style Oak house residence is 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... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 30
    Studio, 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 / 37
    Studio, 3 Bathrooms, Sleeps 14 | Quick View
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    • Waterfront
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    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 / 36
    Studio, 4 Bathrooms, Sleeps 8 | Quick View
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    Note: New for Summer 2017, In ground heated 18 x 30 pool, patio dining table and 6 chaise lounge chairs. Depth of pool 3.5 to 6 feet. Oak Bluffs retreat featuring a pool, outdoor patio, spacious dining deck and three levels of luxury living. The outstanding home has been professionally decorated by... View all property information
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    Oak Bluffs, Martha's Vineyard
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    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    Adorable Beach Chic Cottage and oh so nicely decorated. Walk to Town Center, Harborfront, Parks and Inkwell Beach. Amenities and Features include... Walk to Town and Beach, Wifi Internet Additional amenities include: coffee maker, patio table and chairs, fans - portable, lobster pot, washer /... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 13
    Studio, 1 Bathroom, Sleeps 5 | Quick View
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    Bright and newly remodeled classic summer cottage. Conveniently located just one mile from Oak Bluffs town center, Ink Well Beach, shops, fine and family dining, historic Flying Horses Carousel, public tennis courts, Bandstand Park and Oak Bluffs Harbor-front area. The professionally landscaped... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 28
    Studio, 4 Bathrooms, Sleeps 8 | Quick View
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    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
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    1 / 21
    Studio, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Set in one of the Island's loveliest planned residential areas with beautiful landscaping, overlooking Sengekontacket Pond. Wonderful pond views from all bedrooms and living area. This spacious three floor house is well maintained and attractively decorated. Full deck across back facing pond.... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 19
    5 of 5 bubbles (1) Excellent
    Studio, 3 Bathrooms, Sleeps 9 | Quick View
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    About this property
    Lovely spacious 3+ bedroom, 3.5 bedroom home within a mile from Oak Bluffs Center and beach area. Fully furnished screen porch. This home has been tastefully furnished throughout and will sleep families of 9 comfortably. Amenities and Features include... Stylish New Home, Central AC, Wifi,... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 29
    Studio, 2 Bathrooms, Sleeps 12 | Quick View
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    About this property
    It's all about the stellar location of this five-bedroom Oak Bluffs getaway, a wonderfully renovated Victorian home with a front porch and deck, four bikes to help you explore Martha's Vineyard, and an enclosed yard that is ideal for kids. This two-level house sits just half a mile from the... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 19
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Picturesque ocean views across Farm Pond to Vineyard Sound. Walk to beach and town. Bike path is one block away from this beautifully renovated three bedroom, two bathroom home. Open, airy with lots of glass. The dining and living areas open to deck. Amenities and Features include... Farm Pond... View all property information
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    Oak Bluffs, Martha's Vineyard
    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 / 18
    Studio, 5 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This grand Victorian jewel on Ocean Park has been completely renovated and transformed into a beautiful vacation home. Enjoy water and park views from inside this elegant home, the expansive wraparound porch and the second floor balcony. This beautifully restored Victorian home is a rare find... 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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    About this property
    10 minute walk to Oak Bluffs center and beach area from this lovely modern vacation home. Enjoy all that the summer community of Oak Bluffs has to offer, quaint shops, fine and family dining, harbor front stroll where you will and array of dining establishments, all waterside, boat rentals and... View all property information
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    Oak Bluffs, Martha's Vineyard
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    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities and Features include... Private Pool, High Speed Internet Additional amenities include: coffee maker, patio table and chairs, fans - portable, 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
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    Studio, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Situated on quiet side street with a 15 minute walk or a 5 minute drive to town and beach, this light filled cape offers visiting families a well equipped vacation reprieve featuring comfortable living areas with mini split A/C and a modern spacious kitchen The first level features an open floor... 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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    About this property
    Spacious and pristine four bedroom contemporary located in lovely private down-island community. All new decor, air conditioning, association tennis courts and bike paths. Views from spacious deck across professionally landscaped yard to Sengekontacket Pond. Amenities and Features include...... View all property information
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    Oak Bluffs, Martha's Vineyard
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    1 / 12
    Studio, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Waterview Farm is a private association with wonderful meadow and water views. It is adjacent to Farm Neck Golf and Tennis Club, which is open the public. There is access to Sengekontacket Pond to launch canoes and kayaks from the private association beach. This is also a great spot for children to... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 22
    Studio, 5 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Outstanding, custom crafted estate home with 6 bedrooms and 5.5 bath all nestled on 2 acres of meadow and landscaped grounds overlooking Farm Neck golf course with waterviews of Sengekontacket Pond. Enjoy the expansive and peaceful views across the landscaped grounds , meadows and waterviews in the... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 14
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • Waterfront
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    • x
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    About this property
    This charming home sits atop the Lagoon bluffs w/stairs down to a narrow private beach It offers waterviews from many rooms (including a wonderful glassed in/screened porch). The living room sports bay windows to access the view, and there's a studio w/a private entrance and kitchenette. Outside is... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 14
    4 of 5 bubbles (1) Very good
    Studio, 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
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    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Beautiful Meadow View Farms home, bordered by expansive landscaped yard, peaceful private setting. Association tennis courts just a short distance from the house and Farm Neck Golf and Tennis is just a half mile from the house. Miles of connecting bike paths begin at the entrance to this lovely... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 18
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • x
    About this property
    Adorable Waterfront and Beachfront cottage. Immaculately maintained, lots of summer charm, fantastic views of the Vineyard Sound and Lagoon from the large patio area. Stairs lead directly to private, sandy beach, great area for young children and adults. Kayak enthusiasts will enjoy this waterfront... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 19
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This unique and elegant four bedroom beach cottage is situated on the north shore of Martha's Vineyard. For your relaxation, there is a large porch/patio leading out to the beach affording magnificent views. Additional views from the tastefully decorated living area, bedrooms areas, make this a... 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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    About this property
    This house, built in 1865 it is a unique Victorian home, wonderful for family gatherings. The location is ideal - it sits at the heart of Ocean Park, with the closest access to Circuit Avenue of any of the homes on the Park. The home was recently renovated, including central air with two zones.... 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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    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
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    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    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
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    Oak Bluffs, Martha's Vineyard 02568
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    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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
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    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    Beautiful four bedroom home within walking distance to the Oak Bluffs harbor and town. This home has a nice size first floor living room and separate eat in kitchen. The first floor also has a full bathroom with tub and shower. The second floor has four bedrooms and one full size bathroom. The... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 10
    4 of 5 bubbles (1) Very good
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Spacious, immaculate 4 bedroom, 3 bath home. Large deck for outdoor enjoyment. Situated just outside the busy center of Oak Bluffs. It is a 10 minute walk to all activities, dining, movies and beach, historic Campground Ginger Bread cottages. There are walkways all the way into town. Amenities... View all property information
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    Oak Bluffs, Martha's Vineyard
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    4 of 5 bubbles (1) Very good
    Studio, 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
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 20
    5 of 5 bubbles (59) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    This Oak Bluffs, Martha's Vineyard rental is a certified National Historic Property. Ideal location for visitors in the middle of the most active, multi-cultural, charming, and fun town on Martha's Vineyard. Step outside your door for breakfast or ice cream, a great selection of restaurants in... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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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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    4 of 5 bubbles (1) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Nestled in a private location on Crystal Lake which abounds with bird life, this is a delightful, vintage 1950's home with modern conveniences and comfortable furnishings. Its rambling single story layout is spacious and conducive to relaxed living. It is very well maintained and well equipped. The... 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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    About this property
    Escape to the perfect island getaway at this gorgeous, recently renovated Oak Bluffs home on lovely Martha's Vineyard. Light-filled bedrooms, a playroom, and a huge deck await! Downtown Oak Bluffs is nearby and it's only one mile to the water. If you'd rather remain on the property, you're... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 10
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This gorgeous, contemporary air-conditioned private home is perfect for your luxurious vacation on the island. It is 2700 sq ft of well laid-out space and sits on 1.4 acres of land in a private wooded area, centrally located, only minutes from downtown Oak Bluffs and beautiful beaches. The... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    Studio, 5 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Come and enjoy this three level contemporary home with a beautiful landscaped yard. There is a wonderful deck off the kitchen with outdoor dining and seating area. the first floor offers and open kitchen, dining and TV/living room area. The is a second sitting room on this floor as well. The... 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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    • DVD Player
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This home is Oak Bluffs at its best - close to town but tucked away off a main street, the house is truly a beauty with special, thoughtful details and wonderful furnishings. The new home has the yummiest colors with a handsome, soft blue master bedroom and bath, a twin bedroom in warm gold, one... View all property information
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    Oak Bluffs, Martha's Vineyard
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    Studio, 3 Bathrooms, Sleeps 9 | Quick View
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    • Internet Access
    • Patio
    • Satellite TV
    • DVD Player
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • 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
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    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
    • Waterfront
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Historic harborfront home with private dock has been completely renovated and newly furnished, beautifully appointed throughout to reflect summer living on the Vineyard. The large living and dining areas open onto the expansive and comfortably furnished porch, overlooking picturesque Oak Bluffs... 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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    • Internet Access
    • Grill
    • Satellite TV
    • DVD Player
    • Patio
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This wonderful family vacation home features lovely waterviews across Crystal lake. The peaceful location and large yard provide the perfect venue for extended families with children. Relax on the expansive deck, enjoy the views from the 4 person glider swing as seen in the photos Families will... 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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    • Satellite TV
    • Grill
    • Waterfront
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Beautiful immaculate home, privately located in the Farm Neck area. Extended families will enjoy this open airy home with expansive deck, roomy and comfortably furnished screened porch, great location with easy access to Bike Paths, Oak Bluffs, Edgartown and beaches. Association dock a minute’s... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 32
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
    other traveller has booked this property
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    • Parking
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    • DVD Player
    • Grill
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Relax in optimal comfort at this Oak Bluffs home. It's got four bedrooms and lots of space for an ideal family vacation! You're in the heart of Oak Bluffs, within walking distance of the harbor and lovely waterfront. You can hop off the ferry to Martha's Vineyard and be here in no time. This... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
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    • Satellite TV
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Great Getaway Cottage with a short walk to Circuit Ave, the harbor, and the Lagoon .A back yard w/ picnic table, BBQ grill. About a mile walk or bike ride to Town. The house has hardwood and fir floors throughout and also has air conditioning. This is a great "get away cottage" for a small family... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02557
    1 / 29
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • Waterfront
    • Internet Access
    • DVD Player
    • Washer
    • Parking
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Soak in one of the loveliest sunset views on Martha's Vineyard when you escape to this two-bedroom Oak Bluffs cottage, where you'll enjoy a short walk to the ferries and a private deck with panoramic views of Lagoon Pond, Brush Pond, Vineyard Sound, and Vineyard Haven. This single-level cottage... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 44
    Studio, 3 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Washer
    • DVD Player
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    • Satellite TV
    • Patio
    • Balcony
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Experience the beauty and charming attractions of the Nantucket Sound in this high-end home offering phenomenal New England decor for groups of six. The stylish home offers detailed features like an outdoor shower, stained glass windows, and hand-painted tiles from Jerusalem making it more than... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02557