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Cottages and House Rentals in Oak Bluffs, MA

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    Travelers to Oak Bluffs are booking August dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 19
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 16
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    1 / 19
    5 of 5 stars (1) Excellent
    4 Bedrooms, 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
    Location Information
    Oak Bluffs, Martha's Vineyard
    5 of 5 stars Reviewed July 28, 2014
    Arrived a little early, was able to get keys right away. Lisa, was extremely pleasant to work with. The house was more than I could hope for, just immaculate. The layout was...
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    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
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Pristine 4 bedroom waterfront hideaway. Enjoy spectacular views and sunsets across the lagoon. Private dock for boat enthusiasts. Kayak and boat rentals can be delivered to the property and kayaking on the lagoon is a fun and picturesque activity for the entire family. Centrally located, you are... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 14
    4 of 5 stars (1) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Come experience the magic of the Vineyard in our island home. Modernized in 2011, this charming residence is clean, cozy and boasts new furniture and decor. Amenities include 3 TV’s, cable television, Wi-fi, DVD, telephone, I-home, and Keurig Coffee maker. The property has a private yard, sundeck,... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 13
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Amenities and Features include... In-Town, WiFi Additional amenities include: coffee maker, patio table and chairs, fans - portable, lobster pot, washer / dryer, cd player, landscaped, outside shower - enclosed, outdoor furniture, ironing board. View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 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 August 22, 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 / 13
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    Families are sure to enjoy this cozy home with nautical inspired decor. The main living level offers a spacious living and dining area with cathedral ceiling cooled by window AC. and a neat well equipped kitchen with pass through window. The kitchen opens onto a spacious deck with patio dining and... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
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    1 / 16
    5 of 5 stars (3) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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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 / 27
    6 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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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 / 18
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    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 / 25
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Waterfront
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    About this property
    Adorable waterfront cottage, pristinely maintained throughout the years. Enjoy privacy and views from the spacious deck. 3 minute walk to great sandy lagoon beach - a perfect place for young children to play. Centrally located just 2 miles to either Vineyard Haven or Oak Bluffs town centers.... View all property information
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    Oak Bluffs, Martha's Vineyard
    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
    Location Information
    Oak Bluffs, Martha's Vineyard
    5 of 5 stars 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 / 22
    4 of 5 stars (1) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Grill
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    • Hot Tub
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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
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    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    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 / 13
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • DVD Player
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    About this property
    Little Jaws, the home where the movie Jaws was filmed is a pristine beach cottage. Set in East Chop, this three plus bedroom rental offering features spectacular views, great swimming, kayaking and gorgeous sunsets. Relax on the large and comfortably furnished waterfront veranda. The living room... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 21
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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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
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    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Amenities and Features include... Hidden Cove, Association Tennis Courts, Association Kayak Landing Additional amenities include: coffee maker, fans - portable, lobster pot, food processor, washer / dryer, porch - screened, vacuum, outdoor furniture, tennis - association/shared, ironing board. View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 23
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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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
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    Oak Bluffs, Martha's Vineyard 02539
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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
    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 / 7
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Amenities and Features include... Walk to Town and Beach, Newly Renovated Additional amenities include: coffee maker, patio table and chairs, lobster pot, washer / dryer, landscaped, outdoor furniture, ironing board. View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 16
    6 Bedrooms, 2 Bathrooms, Sleeps 11 | Quick View
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    • x
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    About this property
    Amenities and Features include... In-Town, Walk to Beach, Wifi Internet Additional amenities include: coffee maker, patio table and chairs, fans - portable, lobster pot, washer / dryer, cd player, landscaped, outside shower - enclosed, outdoor furniture, ironing board. View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 24
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
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    About this property
    Spacious and attractive waterfront Cape Cod style home - features gorgeous views, central A/C, Wi-Fi and 4 TV's. Two large decks and a screened porch provide wonderful spaces for summer relaxation in which to enjoy the waterviews. Kayaking enthusiasts will enjoy the gorgeous scenery and wild life... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 13
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    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 / 27
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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
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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 / 20
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Beautiful, spacious, 4 bedroom 3.5 bath contemporary home set in a quiet lovely community on the outskirts of Oak Bluffs. This home comfortably hosts extended families with multiple living spaces. The main living level features an open concept and hosts a family TV room and luncheon breakfast nook,... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 10
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This sweet, little (it's priced accordingly!)cottage is all about convenience. It is within walking distance to the center of Oak Bluffs and two town beaches. The interior of the cottage has recently been redone inside and is fresh & clean and perfect for a great vacation. Large decks, lovely... View all property information
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    Oak Bluffs, Martha's Vineyard 02539
    1 / 37
    7 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • x
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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 / 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
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    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 / 20
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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
    1 / 17
    4 Bedrooms, 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
    1 / 14
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    The quintessential Vineyard cottage!!! This sweet cottage brings back visions of the lazy days of summer of bygone eras when life was less hurried. The serene location overlooks a pond, a barrier beach with a few homes, and the Outer Harbor. It has a magnificent 180 degree view of Vineyard... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    3 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Waterfront
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    • Pet-friendly
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    MVVR EXCLUSIVE: Adorable pristine beach cottage has spectacular views across the sound, calm water swimming, great area for kayaking. The opening kitchen, dining and living areas are enhanced by the wall of windows faciing the waterfront and providing gorgeous water views . Enjoy the parade of... View all property information
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    Oak Bluffs, Martha's Vineyard
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    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
    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
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    • x
    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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • x
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    • 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
    Location Information
    Oak Bluffs, Martha's Vineyard 02557
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
    • Grill
    • Washer
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Ocean Views
    • Housekeeping...
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • DVD Player
    • Patio
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    • Porch
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    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 / 20
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
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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
    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
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    Oak Bluffs, Martha's Vineyard 02557
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | 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
    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 / 22
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Grill
    • DVD Player
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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 / 20
    5 of 5 stars (54) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Porch
    • Satellite TV
    • Grill
    • Ocean Views
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Oak Bluffs, Martha's Vineyard 02557
    5 of 5 stars Reviewed 3 weeks ago
    Love, love, love this apartment. Two bedrooms, spacious living room, and modern equipped kitchen. You'll feel right at home in these comfy quarters with a large balcony...
    5 of 5 stars Reviewed 3 weeks ago
    I cannot say enough good things about our first stay at the Historic Arcade at Oak Bluffs property. We spent 4 days here and have never been more comfortable on vacation. We...
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    1 / 20
    5 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Patio
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Porch
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Gracious 5 bedroom in-town victorian offers easy access to shopping, ferry, park with basketball and tennis and beach. This home has been lovingly maintained and restored to it's prior elegance. Enjoy cocktails on the beautiful three season porch. Additional amenities include: nearby bank, close... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02539