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Oak Bluffs House Rentals

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    Travellers to Oak Bluffs are booking August dates now. Secure your holiday rental today, and have the perfect trip.
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    1 / 9
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Oak Bluffs retreat featuring three levels of luxury living, professionally decorated by one of the islands premier decorators This house is privately situated in an enclave of lovely homes. Bike paths at the entrance connect to miles of biking trails. Farm Neck Golf Course and Restaurant are just a... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 31
    6 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Amenities and Features include... Farm Neck Waterfront Home, Spectacular Views across Sengekontacket Lagoon, Short Walk to Association Lagoon Beach area for Kayaking. One mile to State Beach, Bike paths at entance to Rd run the Full lenght of Beach Rd. Additional amenities include:... View all property information
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    Oak Bluffs, Martha's Vineyard
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Beautiful and spacious 3 bedroom in Oak Bluffs, Martha's Vineyard. Sunny, open and airy Cape. Walking distance to town, gingerbread cottages, library, and playground. Close to beach, golf course, and great fishing spots. There is a pack and play in the upstairs bedroom for a baby to sleep or nap... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This gorgeous, contemporary air-conditioned private home is perfect for your luxurious vacation on the island. It is 2700 sq ft of well laid-out space and sits on 1.4 acres of land in a private wooded area, centrally located, only minutes from downtown Oak Bluffs and beautiful beaches. The... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Just a block from the East Chop Bluffs on a sleepy side street in a quiet wooded setting. There are 2 SEPERATE LIVING ROOMS!! Large bright kitchen that accesses a separate dining room, inviting screen porch with dining and sitting areas, and sunny rear deck with lots of backyard privacy. Ocean... View all property information
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    Oak Bluffs, Martha's Vineyard 02257
    1 / 32
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Relax in optimal comfort at this Oak Bluffs home. It's got four bedrooms and lots of space for an ideal family vacation! You're in the heart of Oak Bluffs, within walking distance of the harbor and lovely waterfront. You can hop off the ferry to Martha's Vineyard and be here in no time. This... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    5 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    About this property
    It's all about the stellar location of this five-bedroom Oak Bluffs getaway, a wonderfully renovated Victorian home with a front porch and deck, four bikes to help you explore Martha's Vineyard, and an enclosed yard that is ideal for kids. This two-level house sits just half a mile from the... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    1 / 29
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Soak in one of the loveliest sunset views on Martha's Vineyard when you escape to this two-bedroom Oak Bluffs cottage, where you'll enjoy a short walk to the ferries and a private deck with panoramic views of Lagoon Pond, Brush Pond, Vineyard Sound, and Vineyard Haven. This single-level cottage... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 50
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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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 / 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
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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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    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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    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    This grand Victorian jewel on Ocean Park has been completely renovated and transformed into a beautiful vacation home. Enjoy water and park views from inside this elegant home, the expansive wraparound porch and the second floor balcony. This beautifully restored Victorian home is a rare find... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    3 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
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    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
    8 Bedrooms, 8 Bathrooms, Sleeps 20 | Quick View
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    • Hot Tub
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    • Terrace
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    • Balcony
    • Central Heating
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    • Pet-friendly
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    • x
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    About this property
    Amazing five acre property! 6 BR main house w/ pool + a 2 BR carriage house! Our amazing property is perfect for everything from a memorable family vacation to a serene retreat. You and your guests will begin to enjoy the feeling of privacy the minute you arrive as you drive down the long tree... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Experience the beauty and charming attractions of the Nantucket Sound in this high-end home offering phenomenal New England decor for groups of six. The stylish home offers detailed features like an outdoor shower, stained glass windows, and hand-painted tiles from Jerusalem making it more than... View all property information
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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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    • DVD Player
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    • Waterfront
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    • Porch
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    • Pet-friendly
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    • x
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    • x
    About this property
    Historic harborfront home with private dock has been completely renovated and newly furnished, beautifully appointed throughout to reflect summer living on the Vineyard. The large living and dining areas open onto the expansive and comfortably furnished porch, overlooking picturesque Oak Bluffs... View all property information
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    Oak Bluffs, Martha's Vineyard
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    1 / 12
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Waterview Farm is a private association with wonderful meadow and water views. It is adjacent to Farm Neck Golf and Tennis Club, which is open the public. There is access to Sengekontacket Pond to launch canoes and kayaks from the private association beach. This is also a great spot for children to... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Beautiful new contemporary house with four bedrooms and four bathrooms, finely appointed and tastefully decorated. Association Tennis, Central A/C, Wifi. This home is located in a highly desirable area close to town and beaches. The house overlooks a meadow and provides the perfect setting for a... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 16
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • x
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    About this property
    East Chop Beauty, bike or walk to town and beach. This designer home features comfortable and elegant décor, central A/C and large lovely yard and flagstone patio. Interior features a large open dining and living area with state of the art kitchen. Custom features throughout. Amenities and... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 23
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • x
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    About this property
    Quietly nestled on quiet street just on the outskirts of town, this brightly lit home features a mix of coastal details and traditionally styled upscale furnishings for your comfort. The interior has open floor plan that flow nicely to outdoor living spaces including a screened porch and brick... 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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    • x
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    • x
    About this property
    Adorable Waterfront and Beachfront cottage. Immaculately maintained, lots of summer charm, fantastic views of the Vineyard Sound and Lagoon from the large patio area. Stairs lead directly to private, sandy beach, great area for young children and adults. Kayak enthusiasts will enjoy this waterfront... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 21
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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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
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Picturesque ocean views across Farm Pond to Vineyard Sound. Walk to beach and town. Bike path is one block away from this beautifully renovated three bedroom, two bathroom home. Open, airy with lots of glass. The dining and living areas open to deck. Amenities and Features include... Farm Pond... View all property information
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    Oak Bluffs, Martha's Vineyard
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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
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    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
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    6 Bedrooms, 2 Bathrooms, Sleeps 11 | Quick View
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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
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Patio
    • Waterfront
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    • x
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    About this property
    This charming home sits atop the Lagoon bluffs w/stairs down to a narrow private beach It offers waterviews from many rooms (including a wonderful glassed in/screened porch). The living room sports bay windows to access the view, and there's a studio w/a private entrance and kitchenette. Outside is... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    3 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    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, 3 Bathrooms, Sleeps 8 | 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 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
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Spacious sun filled contemporary home located on a quiet private street,a 10 minute walk to town center, Inkwell Beach and harborfront, The first level features a spacious kitchen with stainless steel appliances, prep counter with range top. and breakfast nook, there is a comfortable living area... View all property information
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    Oak Bluffs, Martha's Vineyard
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    Spectacular water view in desirable East Chop neighborhood. This 4 bedroom, 3 bath home is just 1.5 miles from Oak Bluffs Center and Beach. There is a yard with multiple decks and waterviews. Features include central air and wifi internet. Beautifully decorated. Amenities and Features include...... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 23
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • x
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    • x
    About this property
    Outstanding, custom crafted estate home with 6 bedrooms and 5.5 bath all nestled on 2 acres of meadow and landscaped grounds overlooking Farm Neck golf course with waterviews of Sengekontacket Pond. Enjoy the expansive and peaceful views across the landscaped grounds , meadows and waterviews in the... View all property information
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    Oak Bluffs, Martha's Vineyard
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    6 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Come and enjoy this beautiful waterfront home on East Chop! The first floor has a wonderful front seasonal porch with views of the Vineyard Sound. There is a large dining table and room to relax and take in the view. There is also a living room that leads into the kitchen on the 1st floor. The... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities and Features include... Additional amenities include: beach chairs, coffee maker, patio table and chairs, lobster pot, washer / dryer, landscaped, outside shower - enclosed, vacuum, outdoor furniture, ironing board. View all property information
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    Oak Bluffs, Martha's Vineyard
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    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    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 kithcen very well stocked with dining and cook items, a large sunporch living area and 2nd aliving area with large screen TV. Three lovely... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 22
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Porch
    • Balcony
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    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Wonderful changes made for the 2016 rental season! Updated granite kitchen now with dishwasher, & garbage disposal. 2nd floor balcony re-opened to gain a better view of the beach. Lots of new furniture for many rooms, new sheets, towels, quilts. NEW outside gas grill with new outdoor dining table &... 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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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Oak Bluffs, Martha's Vineyard
    1 / 13
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Oak Bluffs, Martha's Vineyard
    1 / 14
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • DVD Player
    • Satellite TV
    • Grill
    • Air Conditioning
    • Internet Access
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This home is Oak Bluffs at its best - close to town but tucked away off a main street, the house is truly a beauty with special, thoughtful details and wonderful furnishings. The new home has the yummiest colors with a handsome, soft blue master bedroom and bath, a twin bedroom in warm gold, one... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    1 / 14
    5 of 5 stars (2) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Wi-Fi
    • Satellite TV
    • Grill
    • Porch
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Sun filled and airy prow front contemporary home with beautiful views of Lagoon Pond. Four bedrooms accommodating up to eight guests. Two full baths plus refreshing outdoor shower. The second floor with its cathedral ceiling utilizes an open living room, dining room and kitchen floor plan to... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02557
    1 / 26
    4 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    Amenities & Details
    • Porch
    • DVD Player
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Wonderful four bedroom, two bath home completely redecorated. Features wrap around porch, living room and sun porch/TV room. Amenities and Features include... Classic Oak Bluffs Summer Home, Walk to Town and Beach, On Street Parking Additional amenities include: coffee maker, patio table and... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Patio
    • Grill
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Lovely cape home, all newly refurnished for 2013. First level features an open floor plan in the Dining, Kitchen and Living area. The tastefully decorated living area features comfortable furnishings and a 36" screen tv. One bedroom with a double bed and a full bath complete the living level. 2nd... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    1 / 24
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Internet Access
    • Patio
    • Grill
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Escape to the perfect island getaway at this gorgeous, recently renovated Oak Bluffs home on lovely Martha's Vineyard. Light-filled bedrooms, a playroom, and a huge deck await! Downtown Oak Bluffs is nearby and it's only one mile to the water. If you'd rather remain on the property, you're... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02557
    1 / 19
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Wi-Fi
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Oak Bluffs, Martha's Vineyard 02539
    1 / 12
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    Amenities & Details
    • Patio
    • Satellite TV
    • Porch
    • DVD Player
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Lovely contemporary home in one of the Islands premier community settings, Waterview Farms. Close to Farm Neck Golf Course and tennis and a short distance to town and beaches. Amenities and Features include... Waterview Farms, Waterview Additional amenities include: dock/boat-slip, coffee... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    1 / 33
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    A recent renovation has moved this home to the top of the list in terms of comfort in a tastefully decorated waterfront home. A new family media room has been added giving extended families lots of space to relax. The open concept kitchen, dining and living areas feature waterviews and open onto a... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard