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Cottages and House Rentals in Oak Bluffs, MA

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    1 / 22
    5 of 5 bubbles (3) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    4.5 of 5 bubbles (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 (2) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Newly renovated home across the street from the lagoon and sailing camp! This home features, new stainless steel appliances, granite counter tops with an island. Five minutes away from town and beaches this property is perfectly located. The main floor has central air, an open floor plan with... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02568
    4 of 5 bubbles Reviewed July 15, 2016
    My family and I had a great vacation at Summer Home - By the lagoon. The property is located on a quiet street but, centrally located to downtown Oak Bluffs and other popular...
    5 of 5 bubbles Reviewed June 13, 2016
    This perfect summer rental is perfectly located to all the main locations. You are only minutes from downtown Oak Bluffs and Circuit Ave. The other direction you are minutes from...
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    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
    1 / 26
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    About this property
    This fabulous 125 year-old Victorian cottage was lovingly updated and completely restored in 2012. Sitting on a large private lot, just steps from Inkwell beach, Solera offers the perfect balance of comfort, ambiance and vintage charm. The large, airy gourmet kitchen was featured in This Old House... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 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 / 19
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    This magnificent 1920’s East Chop cottage has been extensively redesigned, refurbished and expanded to allow friends and families to enjoy luxury accommodations along with rare double views of both Nantucket Sound and neighboring Crystal Lake. Complemented with a huge wrap around deck and a covered... View all property information
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    Oak Bluffs, Martha's Vineyard 02568
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    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 / 15
    5 of 5 bubbles (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
    Location Information
    Oak Bluffs, Martha's Vineyard
    5 of 5 bubbles Reviewed August 26, 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 / 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 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    This Seaview condo in Oak Bluffs has a lot to offer. You can walk to the beach and town and also enjoy beautiful waterviews from the patio. This unit is on the first floor with two bedrooms and two bathrooms. There is an open kitchen and living room with big windows that look out into the ocean.... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 19
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Newly renovated and painted campground Victorian home with gingerbread accents. This charming Victorian is ideally located close to town, shops, restaurants and beaches. Enjoy peeks of the harbor while watching the sunset from the new roof top deck. Additional amenities include: coffee maker,... View all property information
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    Oak Bluffs, Martha's Vineyard 02539
    1 / 21
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Completely renovated cottage in the Sunset Lake area of Oak Bluffs. Walk to town and library. Completely renovated modern kitchen. Rock away on the large front porch. Additional amenities include: games, coffee maker, outdoor shower, lobster pot, cd player, wine glasses, fans, vacuum, washer &... View all property information
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    Oak Bluffs, Martha's Vineyard 02539
    1 / 23
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • 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 / 22
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • x
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    • x
    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 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Bright, airy contemporary home located in the wonderful East Chop neighborhood. The first floor features an open concept living room and kitchen. The kitchen has a large island that can seat seven. First floor bedroom is located off of the living room and has access to the full bath. The second... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 / 20
    5 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Patio
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    • x
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    • 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
    1 / 23
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    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
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    1 / 16
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    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 / 20
    8 Bedrooms, 8 Bathrooms, Sleeps 20 | Quick View
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    • Hot Tub
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    • DVD Player
    • Terrace
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    • Balcony
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    • Pet-friendly
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    • x
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    • 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
    1 / 12
    3 Bedrooms, 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 / 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 / 10
    4 Bedrooms, 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
    1 / 22
    7 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    About this property
    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 / 15
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    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 / 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
    1 / 25
    5 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    Renovated beach house in Oak Bluffs with 5 Bedrooms, 2 full baths, Sleeps 8; Large living/dining room, sliding door opens to deck, flagstone picnic area with gas grill, A/C, Washer/Dryer, Free WIFI, Large flat-screen LED TV's with cable service; Located 10-20 min walk to Oak Bluffs harbor, beach... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 30
    6 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Waterfront
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    • x
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    • x
    About this property
    Come and enjoy this beautiful waterfront home on East Chop! The first floor has a wonderful front seasonal porch with views of the Vineyard Sound. There is a large dining table and room to relax and take in the view. There is also a living room that leads into the kitchen on the 1st floor. The... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 16
    5 of 5 bubbles (3) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Wonderful home located about a 10 minute walk to downtown Oak Bluffs. This home has a nice open floor plan for family gatherings, updated furnishings, fully equipped kitchen with stainless steel appliances, Master bath Jacuzzi tub, Entertainment systems include flat screen TVs, CD, DVD, VCR,... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 8
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • x
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    About this property
    A fully renovated four bedroom home with 3 1/2 baths, family room, landscaped lot and a private beach and dock. Dock can accommodate up to a 25 foot motor boat, located on The Lagoon and is accessible to Vineyard Sound. Family room has cable TV, deck, fully equipped kitchen, and a 2 person kayak... 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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    • x
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    About this property
    Walk to town and beach from this spacious modern home on a beautiful, treed lot. A delightful blend of amenities and charm. Central air conditioning. Amenities and Features include... Walk to Town, Central Air, WiFi Additional amenities include: beach chairs, coffee maker, patio table and... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 30
    5 of 5 bubbles (1) Excellent
    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    • x
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    About this property
    Located on over 1 acre of waterfront property on East Chop, an exclusive area of historic Oak Bluffs, this unique home is perfect for family and friends that want to vacation together while maintaining their privacy. This home allows up to 4 families to stay together in the same home while giving... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 23
    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 / 14
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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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 / 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 / 27
    6 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Grill
    • Satellite TV
    • DVD Player
    • Porch
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Sea Glass Cottage Martha's Vineyard Vacation Rentals Sleeps 6. Completely renovated, this charming East Chop cottage will allow its guests to experience all the comforts of modern luxury living combined with the historical splendor of many reclaimed antique furniture pieces from Martha's Vineyard... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
    • DVD Player
    • Satellite TV
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    • Internet Access
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This cozy, quaint waterfront property offers beautiful sunsets and great harbor views. Swimming, boating, kayaking, are just steps from this warm and charming quintessential Vineyard cottage. Amenities and Features include... Waterfront, Waterview Additional amenities include: dock/boat-slip,... View all property information
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    Oak Bluffs, Martha's Vineyard
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Porch
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    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This is a wonderful vacation house located about a 10 minute walk to town and little further to the town beach. The home was recently renovated and has a nice open floor plan on the main level which has an updated kitchen, family room and dining space. There is also a bedroom and full bathroom on... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Patio
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    • Porch
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    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 / 10
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Cozy guest house sleeps 4. Large deck with view of Lagoon. Owner or guests occupy main house. Amenities and Features include... Lagoon Guest House, Walk to Private Lagoon Beach Additional amenities include: coffee maker, patio table and chairs, fans - portable, lobster pot, washer / dryer,... 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
    • ?
    • Smoking allowed
    • 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
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Grill
    • Internet Access
    • Air Conditioning
    • Porch
    • Balcony
    • Satellite TV
    • Patio
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Welcome to the Flying Seahorse, an updated, antique beach cottage that is steps from Oak Bluffs Town Beach, has AC (upstairs, downstairs bedroom and living room), beach views from its balcony, a modern kitchen and plenty of space for extended families. It is an easy walk to downtown (Circuit Ave)... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • DVD Player
    • Satellite TV
    • Grill
    • Patio
    • Porch
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    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
    Location Information
    Oak Bluffs, Martha's Vineyard 02557
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Grill
    • Wi-Fi
    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • 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 / 13
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Grill
    • Wi-Fi
    • Satellite TV
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • 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
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 22
    4 of 5 bubbles (2) Very good
    8 Bedrooms, 3 Bathrooms, Sleeps 16 | Quick View
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    • Satellite TV
    • Wi-Fi
    • Grill
    • Patio
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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 / 20
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Satellite TV
    • Wi-Fi
    • Grill
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    Location Information
    Oak Bluffs, Martha's Vineyard 02557
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