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Vacation Rentals in Oak Bluffs, MA

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    Travellers to Oak Bluffs are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 17
    5 of 5 stars (1) Excellent
    4 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    1 / 17
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    1 / 18
    4.5 of 5 stars (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 19
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
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    About this property
    This magnificent 1920’s East Chop cottage has been extensively redesigned, refurbished and expanded to allow friends and families to enjoy luxury accommodations along with rare double views of both Nantucket Sound and neighboring Crystal Lake. Complemented with a huge wrap around deck and a covered... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 44
    6 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    <BR>*Fall/Winter/Spring multi-week discount available<BR><BR>*Only 3 prime summer weeks left! Check my calendar and book ASAP if you plan to visit in the peak season.<BR><BR>The Pennacook house in Oak Bluffs on the charming island of Martha's Vineyard is beautifully maintained, bright and sunny,... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 9
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Beautiful and spacious 3 bedroom in Oak Bluffs, Martha's Vineyard. Sunny, open and airy Cape. Walking distance to town, gingerbread cottages, library, and playground. Close to beach, golf course, and great fishing spots. There is a pack and play in the upstairs bedroom for a baby to sleep or nap... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 38
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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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... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 33
    5 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Set in a quiet community of homes just on the outskirts of OB, this outstanding home provides a peaceful get away yet is just a short drive to town center. The use of coastal colors and upscale furnishings throughout combine to make this gorgeous Oak Bluffs summer home a cut a above. Expansive... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 19
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Internet Access
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    About this property
    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... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 20
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Situated on quiet side street with a 15 minute walk or a 5 minute drive to town and beach, this light filled cape offers visiting families a well equipped vacation reprieve featuring comfortable living areas with mini split A/C and a modern spacious kitchen The first level features an open floor... View all property information
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    Oak Bluffs, Martha's Vineyard
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    1 / 21
    5 of 5 stars (2) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Delightful summer cottage. Great family home for relaxing on the large deck, kayaking the lagoon, great play beach on the lagoon for children. The bunk house with two bedrooms is directly behind the main part of the house, about 10 steps across the yard. The views are spectacular and expansive.... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    5 of 5 stars Reviewed 25 July 2014
    The house was perfect for our family. The views from the deck, family room and bedrooms were incredible. We ended up grilling 4 out of the 7 nights we were there because there is...
    5 of 5 stars Reviewed 18 July 2014
    I would love to say it was an awful stay so no one else would want to stay there but us, but truth be told - it was GLORIOUS. We so enjoyed sitting on the deck in the morning...
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    1 / 13
    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
    1 / 15
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Crisp, elegant and tastefully decorated. This lovely 2 bedroom, 2 bath condo is across the street from the beach and a 5 minute waterfront walk to town, ferry, movies, galleries, dining and entertainment. Enjoy the spectacular views from your balcony or cross the street for a morning swim. Great... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    5 of 5 stars Reviewed 26 August 2014
    ...second floor 2 bed room 2 bath condo with balcony that overlooks Inkwell Beach in Oak Bluffs on Martha"s Vineyard...great walkable location to Oak Bluff's Circuit Avenue for...
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    1 / 18
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Patio
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    • x
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    About this property
    Adorable Waterfront and Beachfront cottage. Immaculately maintained, lots of summer charm, fantastic views of the Vineyard Sound and Lagoon from the large patio area. Stairs lead directly to private, sandy beach, great area for young children and adults. Kayak enthusiasts will enjoy this waterfront... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 15
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Waterview Farm boasts views across peaceful meadows to Sengekontacket Pond and beyond. Launch canoes and kayaks at private association beach on the pond. Great location for families. Close to bike paths, town and beaches. House has an open, airy floor plan and large deck. Amenities and Features... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 27
    6 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Grill
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    About this property
    Seaside Cottage Style Vacation Home. Recently renovated. Perfect for extended families. Walk to Oak Bluffs town center, beach across the street and miles of beach side - bike paths begin just a couple of hundred yards from the house. Ocean views from just about all rooms. Wonderful, large summer... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 28
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Porch
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    • x
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    About this property
    Extended families are sure to enjoy this Tri-level home featuring open floor plan on the main level, large main living room and two den TV areas one on the first level one and an additional TV area on the 2nd level. Kitchen has stainless appliance and granite counters and the family dining area is... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 31
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Waterfront
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    • x
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    About this property
    Architect designed luxury waterfront retreat sits overlooking 500 feet of private lagoon beach and maintains sweeping waterviews up the lagoon. The pool and patio areas take full advantage of the views. Dine and relax by the pool with pool side hot tub and the all new deck being constructed with... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 15
    3 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
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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 open kitchen, dining and living areas are enhanced by the wall of windows facing the waterfront and providing gorgeous water views . Enjoy the parade of... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 43
    6 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    About this property
    The Weku House is a luxury, 5,000 square foot home located in the beautiful town of Oak Bluffs on Martha’s Vineyard. Originally built in the year 2000, this home was fully renovated in 2015. Elegantly decorated with designer furnishings and interior appointments, the meticulous attention-to-detail... View all property information
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    Oak Bluffs, Martha's Vineyard
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    1 / 22
    6 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • 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
    1 / 15
    7 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • ?
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    • x
    About this property
    This classic Gingerbread House is less than a block away from the beach in Oak Bluffs. Surrounded by parks in a residential neighborhood, the property is easy walking distance to shops, restaurants, harbor, galleries, etc.. This house is spacious with high ceilings and over-sized rooms. The... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 13
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    Bright and newly remodeled classic summer cottage. Conveniently located just one mile from Oak Bluffs town center, Ink Well Beach, shops, fine and family dining, historic Flying Horses Carousel, public tennis courts, Bandstand Park and Oak Bluffs Harbor-front area. The professionally landscaped... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 61
    5 of 5 stars (1) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 22 | Quick View
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    • Hot Tub
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    • x
    About this property
    This upscale, newly renovated, 4 bedroom home in a quiet neighborhood in Oak Bluffs. You are 2.5 miles from the town center and Inkwell and State beautiful public beaches. This home boasts a large unground back yard pool and hot tub on the mahogany deck. Large outdoor shower. Grill and fire pit... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 19
    5 of 5 stars (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • x
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    About this property
    Lovely spacious 3+ bedroom, 3.5 bedroom home within a mile from Oak Bluffs Center and beach area. Fully furnished screen porch. This home has been tastefully furnished throughout and will sleep families of 9 comfortably. Amenities and Features include... Stylish New Home, Central AC, Wifi,... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    5 of 5 stars Reviewed 28 July 2014
    Arrived a little early, was able to get keys right away. Lisa, was extremely pleasant to work with. The house was more than I could hope for, just immaculate. The layout was...
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    1 / 11
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Walk to Oak Bluffs town center or Inkwell beach from this fabulous beach-chic cottage with all new furnishings in 2014. Open floor plan with high ceilings, but cozy and comfortable. Two bedrooms upstairs both with Queen-sized beds. Full bath downstairs with front-load washer/dryer. Modern,... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 12
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • x
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    About this property
    Lovely contemporary home in one of the Islands premier community settings, Waterview Farms. Close to Farm Neck Golf Course and tennis and a short distance to town and beaches. Amenities and Features include... Waterview Farms, Waterview Additional amenities include: dock/boat-slip, coffee... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 27
    5 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    About this property
    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.... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 19
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    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
    1 / 7
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Amenities and Features include... Walk to Town and Beach, Newly Renovated Additional amenities include: coffee maker, patio table and chairs, lobster pot, washer / dryer, landscaped, outdoor furniture, ironing board. View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • 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
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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
    1 / 22
    6 Bedrooms, 3 Bathrooms, Sleeps 13 | Quick View
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    • x
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    About this property
    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,... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 9
    4 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    This whimsical summer home located in Water View Farms, provides a peaceful retreat overlooking wild flower meadows. Launch canoes or kayaks from the private association beach on Sengekontacket Pond, just a short walk from the house. Great waterfront play area for young children at the association... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 10
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Cozy guest house sleeps 4. Open floor plan with queen bed alcove off of living room. One bedroom with one set of bunk beds. Large deck with view of Lagoon. Owner or guests occupy main house. Amenities and Features include... Lagoon Guest House, Walk to Private Lagoon Beach Additional amenities... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 12
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    This cozy, quaint waterfront property offers beautiful sunsets and great harbor views. Swimming, boating, kayaking, are just steps from this warm and charming quintessential Vineyard cottage. Amenities and Features include... Waterfront, Waterview Additional amenities include: dock/boat-slip,... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 24
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Spacious and attractive waterfront Cape Cod style home - features gorgeous views, central A/C, Wi-Fi and 4 TV's. Two large decks and a screened porch provide wonderful spaces for summer relaxation in which to enjoy the waterviews. Kayaking enthusiasts will enjoy the gorgeous scenery and wild life... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 16
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Adorable Beach Chic Cottage and oh so nicely decorated. Walk to Town Center, Harborfront, Parks and Inkwell Beach. Amenities and Features include... Walk to Town and Beach, Wifi Internet Additional amenities include: coffee maker, patio table and chairs, fans - portable, lobster pot, washer /... View all property information
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    Oak Bluffs, Martha's Vineyard
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Grill
    • DVD Player
    • Patio
    • Internet Access
    • Porch
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Gorgeous Meadow View Farms home bordered by expansive landscaped yard, Association tennis courts just a short distance from the house and Farm Neck Golf and Tennis is just a half mile from the house.Connecting bike paths begin at the entrance to Meadow View. This sun filled contemporary home... View all property information
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    Oak Bluffs, Martha's Vineyard
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Grill
    • Satellite TV
    • Waterfront
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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... 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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    • Satellite TV
    • Internet Access
    • DVD Player
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Open, airy contemporary Cape. All newly furnished, three bedrooms, 2 bathrooms. Ceiling fans in all bedrooms. A short 15 minute walk to Oak Bluffs Center and Beach, shopping, and dining. Sidewalks connect to miles of bike paths. Amenities and Features include... Walk to Town. Hi Speed Internet.... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    1 / 30
    7 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • Grill
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    In Town, walk to beach, tennis and town area. This wonderful family home has a large wrap around porch, 7 bedrooms and sleeps 12-14. Many areas of this wonderful older home have been updated. Hi Speed Internet. Amenities and Features include... 1 Block to Beach, Wifi Internet, Linens Provided,... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
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    • Central Heating
    • Wi-Fi
    • Grill
    • Washer
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    This charming Cape style Oak house residence is 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... 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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    • Internet Access
    • Satellite TV
    • DVD Player
    • 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
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Please note - all new master bedroom and bath completed in 2014 (not shown in photos) Amenities and Features include... Sengekontacket, Central Air Additional amenities include: coffee maker, patio table and chairs, lobster pot, food processor, washer / dryer, cd player, landscaped, outside... View all property information
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    Oak Bluffs, Martha's Vineyard
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    6 Bedrooms, 2 Bathrooms, Sleeps 11 | Quick View
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    • Grill
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    • Satellite TV
    • Porch
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Oak Bluffs, Martha's Vineyard
    1 / 9
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
    • Satellite TV
    • Secure Parking
    • Balcony
    • Wi-Fi
    • Ocean Views
    • Terrace
    • Private Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This is an original Pratt house built in 1866 by the famed architect Pratt for whom the Pratt Institute in New York was named. It is located in the historic district across from a large park in which baseball, golf practice, kite flying, bike riding, picnics and even, on at least one occasion,... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 12
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Internet Access
    • Satellite TV
    • Grill
    • Porch
    • Patio
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    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... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 14
    5 of 5 stars (3) Excellent
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
    • DVD Player
    • Grill
    • Wi-Fi
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
    1 / 25
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Waterfront
    • Grill
    • DVD Player
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Adorable waterfront cottage, pristinely maintained throughout the years. Enjoy privacy and views from the spacious deck. 3 minute walk to great sandy lagoon beach - a perfect place for young children to play. Centrally located just 2 miles to either Vineyard Haven or Oak Bluffs town centers.... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard