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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.
    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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    4.5 of 5 bubbles (2) Very good
    3 Bedrooms, 3 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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    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
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    Oak Bluffs, Martha's Vineyard 02557
    5 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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    1 / 17
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
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    About this property
    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... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 14
    5 of 5 bubbles (3) Excellent
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick 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.... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Stay in this peaceful, well-maintained home with a large wrap-around porch, a deck, and in close proximity to the ocean for your next unforgettable New England vacation. Come with a small group of friends, bring your own small family, or get away with another couple and rest assured that you'll... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 21
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This charming home is situated in an idyllic private wooded setting on Sengekontacket Pond, one of the largest salt-water ponds on Martha's Vineyard. Comfortably furnished, it has a newlyr renovated kitchen and a new dining area overlooking Major's Cove. There is also a new screened in sun room for... 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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    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
    1 / 7
    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • Outdoor Dining Area
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    A comfortable ranch with all the amenities for a perfect vacation. It's quiet location is 1.5 miles from town, yet not too far to bike or walk in when needed. Beaches, ponds, the lagoon, and other recreational facilities are also easily accessible if you want to hop on the bike path around the... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    1 / 40
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Terrace
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    • Pet-friendly
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    About this property
    This classic Oak Bluffs home is filled with antiques and has views of the pier from the front porch. It's the perfect home for families wanting a relaxing getaway. This historic cottage is only five minutes away from Ink Well Beach and the Steamship Authority Dock, and is just a half mile from the... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 17
    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Charming six bedroom home located within walking distance to town. The first floor has a nice living room/dining area with doors that open to the front porch. There are two bedroom and one full bath on the first floor too. The second floor has four additional bedrooms and two bathrooms. There... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 23
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Immaculate, waterview town house located in the desirable Sengekontacket Pond area of Oak Bluffs. Wonderful waterviews of Sengkontacket Pond and Nantucket Sound. This spacious unit offers a bright open airy feeling with three levels of living area. The main floor includes bedroom, living, dining... View all property information
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    Oak Bluffs, Martha's Vineyard 02539
    1 / 9
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • Porch
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beautiful and spacious 3 bedroom in Oak Bluffs, Martha's Vineyard. Sunny, open and airy Cape. Walking distance to town, gingerbread cottages, library, and playground. Close to beach, golf course, and great fishing spots. There is a pack and play in the upstairs bedroom for a baby to sleep or nap... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 22
    6 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • DVD Player
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    • Waterfront
    • Porch
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Historic summer "cottage" with 7 bedrooms, sleeping porches, a deck overlooking the water, a private dock on Harthaven Harbor, and immediate access to the ocean. The rustic home is a perfect gathering spot for family and friends. It has a large living room with a huge stone fireplace, an eat-in... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 21
    5 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    Beautiful luxury home overlooking Farm Neck Golf Course and Sengekontacket Pond. Large family living spaces include a great room with soaring ceilings opening to the patio as well as a large TV/family room. Expansive gourmet kitchen with dining area is great for family gatherings after the beach.... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 21
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    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 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    Come and enjoy the newly renovated two bedroom home in Oak Bluffs. The first floor which is done in bright coastal colors has a nice eat in kitchen with a couple steps up to the living room with a large flat screen TV. The first floor also have a half bath. The second floor has two bedrooms and... View all property information
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    Oak Bluffs, Martha's Vineyard 02577
    1 / 22
    7 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • Satellite TV
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    • x
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    • x
    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 / 20
    5 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Air Conditioning
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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
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    1 / 18
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Enjoy the charm of a Vineyard cottage with all the amenities of today. This 3 bedroom house has brand new furnishings for 2015. It is in a quiet neighborhood not far from Oak Bluffs center and its harbor. The house is also close to the bike path. The house has an open floor plan with a large... View all property information
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    Oak Bluffs, Martha's Vineyard 02539
    1 / 19
    7 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • x
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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 / 24
    3 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    • Balcony
    • Patio
    • Central Heating
    • Washer
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    • Parking
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    • DVD Player
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    • Pet-friendly
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    • x
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    Location Information
    Oak Bluffs, Martha's Vineyard 02557
    1 / 10
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
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    • Pet-friendly
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    • x
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    • x
    About this property
    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 / 18
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Spacious contemporary 4 bedroom 3.5 bath home located in one Oak Bluffs most exclusive neighborhoods. This house offers many features such as hardwood floors, central air conditioning, and a large living dining area with walk out deck and patio. The yard is nicely landscaped with waterviews over... View all property information
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    Oak Bluffs, Martha's Vineyard 02539
    1 / 21
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
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    • x
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    About this property
    Set in one of the Island's loveliest planned residential areas with beautiful landscaping, overlooking Sengekontacket Pond. Wonderful pond views from all bedrooms and living area. This spacious three floor house is well maintained and attractively decorated. Full deck across back facing pond.... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 16
    5 of 5 bubbles (3) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    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 / 15
    5 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Come and let your cares float away as you relax on the enormous first-floor front porch or second-floor open deck of this charming 100+-year-old home looking out onto the beautiful Nantucket Sound. The home is sunny, bright and spacious and has a relaxed elegance with a large open living room... 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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    • Washer
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    • Ocean Views
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    • Pet-friendly
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    • x
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    • x
    About this property
    This fabulous 125 year-old Victorian cottage was lovingly updated and completely restored in 2012. Sitting on a large private lot, just steps from Inkwell beach, Solera offers the perfect balance of comfort, ambiance and vintage charm. The large, airy gourmet kitchen was featured in This Old House... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 20
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    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... 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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    • x
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    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 / 25
    5 of 5 bubbles (1) Excellent
    7 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • Waterfront
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    • Pet-friendly
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    • x
    • ?
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    • x
    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 allowing for separation. This home can accommodate up to 12 people. No longer need to rent multiple homes on... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 14
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    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... View all property information
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    Oak Bluffs, Martha's Vineyard 02568
    1 / 44
    2 of 5 bubbles (1) Poor
    6 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    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... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 20
    5 of 5 bubbles (59) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Ocean Views
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    • ?
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    • 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
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    Oak Bluffs, Martha's Vineyard 02557
    5 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...
    5 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 it...
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    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 / 30
    4 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    New to the 2015 Summer Season! This spacious waterfront home offers 4-bedrooms en-suite, with family, game and fitness rooms...and yes, a pool. The peaceful setting is centrally located, yet close to the village center for easy access to shops, restaurants and more. The home is tastefully... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Wonderful, spacious, lovingly maintained and attractive home in exclusive setting - family room with fireplace, large formal living room with fireplace, master bedroom with full private bath. Large kitchen and dining area that opens onto wonderful deck. Association tennis and boat landing on... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    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
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    6 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Waterfront
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    • x
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    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
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    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 of 5 bubbles (1) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Walk to town from this meticulously maintained, large & airy, 3 bedroom, 3 full bathroom vacation getaway, located on a beautiful 1/4 acre lot on a quiet street. Watch your troubles sail away while relaxing on the large farmer's porch with your favorite summer beverage, or grilling with family and... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    5 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • x
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    • x
    About this property
    It's all about the stellar location of this five-bedroom Oak Bluffs getaway, a wonderfully renovated Victorian home with a front porch and deck, four bikes to help you explore Martha's Vineyard, and an enclosed yard that is ideal for kids. This two-level house sits just half a mile from the... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    8 Bedrooms, 8 Bathrooms, Sleeps 20 | Quick View
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    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
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    4 of 5 bubbles (1) Very good
    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • x
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    • x
    About this property
    This well maintained, vintage Victorian home is centrally located, yet away from the hustle and bustle of town: just one block from the beach, two blocks from Waban Park and Ocean Park, three blocks from tennis, backetball and a playground and four blocks from town. Enjoy the waterview of Vineyard... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    4 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • x
    About this property
    New Renovated, 1870 historic "Campground" cottage centrally located in Oak Bluffs, The cottage has 4 bedrooms (all located on the second floor) - 1 queen, 2 double beds and 2 twins beds. The front bedroom has its own balcony with water views. Cottage sleeps 8. the first floor includes a newly... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Sitting on the "summer porch" (that is what they were called in the days of old) sipping your favorite beverage, strolling the short distant to the water, relaxing around the table, Well equipped kitchen, reading in the living room with your feet these are possible when you stay in this well cared... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • x
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    • x
    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
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    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
    Location Information
    Oak Bluffs, Martha's Vineyard 02257
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