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Oak Bluffs Vacation Rentals

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    Travelers to Oak Bluffs are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    2 Reviews
    3 Bedrooms, Sleeps 6Quick View
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    3 Bedrooms, Sleeps 6Quick View
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    3 Bedrooms, Sleeps 6Quick View
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    6 Bedrooms, Sleeps 10Quick View
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    • Satellite TV
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    About this property
    *Fall/Winter/Spring multi-week discount available *Only 1 prime summer week left! Check my calendar and book ASAP if you plan to visit in the peak season. *Perfect location so No Car Needed. Easy walk to town, beach & parks. The Pennacook house in Oak Bluffs on the charming island of Martha's...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 6 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, Sleeps 9Quick View
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    • Satellite TV
    • Balcony
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    JUNE & JULY RATES REDUCED!!<BR><BR>You will be within walking distance from downtown shopping, movie theatre, restaurants, bike path, harbor, beaches, and two-tenths of a mile from the brand-new modern library.<BR><BR>Relaxed and warm, this brand-new home is expertly decorated. The open floor plan...
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    Oak Bluffs, Martha's Vineyard 02568
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    1 Review
    4 Bedrooms, Sleeps 8Quick View
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    Excellent of 5 bubbles
    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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    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...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    2 Reviews
    3 Bedrooms, Sleeps 6Quick View
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    • Terrace
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    About this property
    Adorable GINGER BREAD house in Oak Bluffs that I rent out for 6 weeks each summer. Best location! It's a 2 minute walk to the harbor, town restaurants, shops and bars. The OCEAN is a 6 minute walk! House is adorable, furnished, AC in some rooms, parking. Overlooking a park, sip your coffee on the...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, Sleeps 4Quick View
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    Beautiful home in a quiet area, near all the shopping. Walk to beaches and the center of Oak Bluffs. On the bus line between Oak Bluffs and Vineyard Haven/Tisbury. Contemporary style, full kitchen, outdoor shower, deck and grill, parking. Sunny and private and feels like it's in the woods. Two...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    About this property
    Note: This home will have all new furnishings, beds and decor items for summer 2017. The house is being completely painted and all new hardwood floors are being added to areas where carpeting may appear in the current photos. Current photos are of furnishings from previous owner. New photos of the...
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    Oak Bluffs, Martha's Vineyard 02568
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    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...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    7 Bedrooms, Sleeps 14Quick View
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    Classic, "Camp Ground" over sized 7 bedroom 3 bath home in a residential neighborhood within easy walking distance to the beach, shops, restaurants, galleries, etc. It offers double master bedrooms (1st and 2nd floor.) Enjoy rocking on our huge front porch in over sized Georgia rockers. As you...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 7 Bedrooms, 3 Bathrooms, Sleeps 14
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    6 Bedrooms, Sleeps 13Quick View
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    This outstanding Oak Bluffs home is undergoing a complete face lift for the 2012 rental season and is sure to please. Spacious and perfect for extended families, featuring multiple attractively furnished living areas and sleeping 13 comfortably. The lower level of the house features a queen bed,...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 6 Bedrooms, 3 Bathrooms, Sleeps 13
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    Privately situated on a hilltop in Sengkontacket, -spacious tri-leve 4000 sq ft contemporary home. This wonderful vacation home has been updated for summer 2015, AC added, freshly painted, new carpeting and hardwood flooring and new furnishings. Set in a wonderful family friendly community offering...
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    Oak Bluffs, Martha's Vineyard 02568
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 12
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    About this property
    All newly remodeled and furnished and tucked away on a quiet Oak Bluffs lane for the perfect reprieve after a day at the beach and shopping in town, along the Oak Bluffs harbor - and all just a short drive or bike ride away. This vacation home looks and feels so comfortable when you first walk in....
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    Oak Bluffs, Martha's Vineyard 02568
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 6Quick View
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    About this property
    If you are looking for an immaculate, charming, cottage style, yet modern home and close to Oak Bluffs center look no further. This recently updated 3 bedroom, 2 bath home features sunny open living, kitchen and dining areas. Soft seashore color palette throughout adds to the ambiance of this great...
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    Oak Bluffs, Martha's Vineyard 02568
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Review
    6 Bedrooms, Sleeps 12Quick View
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    This well maintained, vintage Victorian home is centrally located, yet away from the hustle and bustle of town: just one block from the beach, two blocks from Waban Park and Ocean Park, three blocks from tennis, backetball and a playground and four blocks from town. Enjoy the waterview of Vineyard...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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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...
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    Oak Bluffs, Martha's Vineyard 02568
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    2 Bedrooms, Sleeps 4Quick View
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    This sweet, little (it's priced accordingly!)cottage is all about convenience. It is within walking distance to the center of Oak Bluffs and two town beaches. The interior of the cottage has recently been redone inside and is fresh & clean and perfect for a great vacation. Large decks, lovely...
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    Oak Bluffs, Martha's Vineyard 02539
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Reviews
    5 Bedrooms, Sleeps 10Quick View
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    About this property
    Classic & charming, turn of the century "campground" home situated on a 4,400 sq. ft. corner lot just a few minutes walk from the beach & town. Spacious & light rooms w/ some intimate spaces, a formal dining room, hardwood & pine floors, and a sweet porch all blend into a wonderful vacation spot....
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    Smoking allowed
    About this property
    Walk to Oak Bluffs town center, ferry or Inkwell Beach from this beach-chic recently renovated and adorable cottage. Upon entering you are greeted with an open floor plan in the living kitchen and dining areas. The living room is tastefully and comfortable furnished and has a 42" flat screen TV....
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    Oak Bluffs, Martha's Vineyard 02568
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Penacook 5 Bedroom Cottage - short stroll down one of the nicest streets in Oak Bluffs to the beach in one direction and town center in the other, where you will find shops, eateries,- gourmet and family style, entertainment, the historic Flying Horsed Carousel, and the beautiful harborfront area....
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    Oak Bluffs, Martha's Vineyard 02568
    Rental Home - 5 Bedrooms, 1 Bathroom, Sleeps 8
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    4 Bedrooms, Sleeps 8Quick View
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    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...
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    Oak Bluffs, Martha's Vineyard 02568
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    European-styled cottage is tucked away down a private lane surrounded by private yard with gardens - you’ll feel like you have completely gotten away from it all. The front door opens into a classic Mudroom with an antique wood, stadium bench seat - and then you step into the open and airy Great...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, Sleeps 6Quick View
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    Sea Glass Cottage Martha's Vineyard Vacation Rentals Sleeps 6. Completely renovated, this charming East Chop cottage will allow its guests to experience all the comforts of modern luxury living combined with the historical splendor of many reclaimed antique furniture pieces from Martha's Vineyard...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 8Quick View
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    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 &...
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    Oak Bluffs, Martha's Vineyard 02539
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 5Quick View
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    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...
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    Oak Bluffs, Martha's Vineyard 02536
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    • Grill
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    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...
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    Oak Bluffs, Martha's Vineyard 02568
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    6 Bedrooms, Sleeps 12Quick View
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    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....
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    Cute and Cozy guest house with open floor plan in the kitchen, living and alcove sleeping area with queen bed. This cottage is perfect for couples, the owner will consider one additional child. There is a den with futon sofa separate from the main part of the cottage. Relax on the deck while you...
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    Oak Bluffs, Martha's Vineyard 02568
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, Sleeps 3Quick View
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    Tiny beach cottage, a rare find these days and just perfectly cute. The cottage is located along the waterfront on East Chop Drive, a very desirable area of Oak Bluffs. The porch looks out over the beach and beyond to the Vineyard Sound. Relax on the covered porch and take in the outstanding...
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    Oak Bluffs, Martha's Vineyard 02568
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Charming Gingerbread Cottage located in the Tabernacle area of Oak Bluffs. A short stroll brings you to Oak Bluffs Center with shops, family and fine dining, harbor area, bandstand park, and Ink Well Beach. Recently updated, this house features a modern eat in kitchen opening to the back deck and...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    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,...
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    Oak Bluffs, Martha's Vineyard 02568
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    8 Bedrooms, Sleeps 16Quick View
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    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...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 8 Bedrooms, 3 Bathrooms, Sleeps 16
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    7 Bedrooms, Sleeps 12Quick View
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    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...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 7 Bedrooms, 3 Bathrooms, Sleeps 12
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    • Washer
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    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...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    4 Bedrooms, Sleeps 8Quick View
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    About this property
    Immaculate, waterview town house located in the desirable Sengekontacket Pond area of Oak Bluffs. Wonderful waterviews of Sengkontacket Pond and Nantucket Sound. This spacious unit offers a bright open airy feeling with three levels of living area. The main floor includes bedroom, living, dining...
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    Oak Bluffs, Martha's Vineyard 02539
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, Sleeps 12Quick View
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    Just a block from the East Chop Bluffs on a sleepy side street in a quiet wooded setting. There are 2 SEPERATE LIVING ROOMS!! Large bright kitchen that accesses a separate dining room, inviting screen porch with dining and sitting areas, and sunny rear deck with lots of backyard privacy. Ocean...
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    Oak Bluffs, Martha's Vineyard 02257
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Air conditioning has been added for the 2017 season! 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...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Reviews
    3 Bedrooms, Sleeps 6Quick 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,...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Classic vineyard cottage renovated, tastefully and comfortably furnished. Large open deck on both the main and 2nd levels. Main living level features a lovely kitchen very well stocked with dining and cook items, a large sunporch living area and 2nd living area with large screen TV. Three lovely...
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    Oak Bluffs, Martha's Vineyard 02568
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    59 Reviews
    2 Bedrooms, Sleeps 5Quick View
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    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Porch
    • Satellite TV
    • Grill
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed November 13, 2016
    This rental is the best place to stay for our family. We've been returning every year to stay at the Historic Arcade Building for about 8 years. The location is perfect, walking...
    Excellent of 5 bubbles
    Reviewed October 10, 2016
    We have been staying at this apartment for years now. We look forward all year to going back to the same place. We now have come to refer to it as home! We love the location as...
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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...
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    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    For those who love an in-town location this area known as the Campground with the historic Tabernacle is the ideal location. The sweet and colorful cottage is pristinely maintained by the owner. Rockers line the porch for your outside enjoyment. The main level hosts the living room with TV ( not...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, Sleeps 8Quick View
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    Amenities & Details
    • DVD Player
    • Grill
    • Satellite TV
    • Waterfront
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful waterfront home with central A/C, features open floor plan and sunny living spaces. The great room has two distinct seating areas and is equipped with a flat screen TV. There is a formal dining room set between the living area and kitchen and opens to the outdoor patio with gorgeous...
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    Oak Bluffs, Martha's Vineyard 02568
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    6 Bedrooms, Sleeps 10Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Oak Bluffs, Martha's Vineyard 02568
    Rental Home - 6 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Reviews
    6 Bedrooms, Sleeps 10Quick View
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    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Ocean Views
    • Grill
    • Patio
    • Satellite TV
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterview - located on the East Chop Vineyard Highlands overlooking Nantucket Sound, Oak Bluffs harbor, Sunset Lake, and 3 acre Washington Park, this charmingly original 1860's Vineyard cottage is an ideal family vacation home. Leave the car on the mainland or in the driveway, for everything,...
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    Oak Bluffs, Martha's Vineyard 02568
    Rental Home - 6 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, Sleeps 8Quick View
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    • Air Conditioning
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    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious contemporary 4 bedroom 3.5 bath home located in one Oak Bluffs most exclusive neighborhoods. This house offers many features such as hardwood floors, central air conditioning, and a large living dining area with walk out deck and patio. The yard is nicely landscaped with waterviews over...
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    Oak Bluffs, Martha's Vineyard 02539
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    • Satellite TV
    • Wi-Fi
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A new Cape style residence situated on a wooded lot near bike path and just a short ride to town center and ferry. This home features an open design with a bright kitchen/dining/living area with hardwood floors, den and full bath on the first floor. Sliders in the dining area lead out onto a nice...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Air Conditioning
    • Satellite TV
    • Grill
    • DVD Player
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxury waterfront home with dock, deep water mooring, a private beach as well as deep water access and marina facilities close-by. Enjoy a commanding view of Lagoon Pond with gorgeous westerly sunsets - second to none! This home offers a spacious open floor plan providing a comfortable yet elegant...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Review
    5 Bedrooms, Sleeps 22Quick View
    other travelers have booked this property
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    • Hot Tub
    • Satellite TV
    • Washer
    • Patio
    • Grill
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 22
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    • Air Conditioning
    • Grill
    • Wi-Fi
    • DVD Player
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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,...
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    Oak Bluffs, Martha's Vineyard 02539
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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