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Holiday Homes and Apartments Oak Bluffs, MA

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    Travellers to Oak Bluffs are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 17
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    1 / 18
    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 17
    5 of 5 stars (1) Excellent
    4 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    1 / 16
    3 of 5 stars (2) Average
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Terrace
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    About this property
    Adorable GINGER BREAD house in Oak Bluffs that I rent out for 6 weeks each summer. Best location! It's a 2 minute walk to the harbor, town restaurants, shops and bars. The OCEAN is a 6 minute walk! House is adorable, furnished, AC in some rooms, parking. Overlooking a park, sip your coffee on the... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 61
    5 Bedrooms, 4 Bathrooms, Sleeps 22 | Quick View
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    • Hot Tub
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    • Washer
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    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 02557
    1 / 13
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    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 / 9
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
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    • Ocean Views
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    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 02557
    1 / 16
    5 of 5 stars (3) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Wonderful home located about a 10 minute walk to downtown Oak Bluffs. This home has a nice open floor plan for family gatherings, updated furnishings, fully equipped kitchen with stainless steel appliances, Master bath Jacuzzi tub, Entertainment systems include flat screen TVs, CD, DVD, VCR,... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 19
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Internet Access
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    • Porch
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    • Waterfront
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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 / 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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    1 / 10
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This sweet, little (it's priced accordingly!)cottage is all about convenience. It is within walking distance to the center of Oak Bluffs and two town beaches. The interior of the cottage has recently been redone inside and is fresh & clean and perfect for a great vacation. Large decks, lovely... View all property information
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    Oak Bluffs, Martha's Vineyard 02539
    1 / 22
    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 / 13
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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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 / 14
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    The quintessential Vineyard cottage!!! This sweet cottage brings back visions of the lazy days of summer of bygone eras when life was less hurried. The serene location overlooks a pond, a barrier beach with a few homes, and the Outer Harbor. It has a magnificent 180 degree view of Vineyard... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 21
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Completely renovated cottage in the Sunset Lake area of Oak Bluffs. Walk to town and library. Completely renovated modern kitchen. Rock away on the large front porch. Additional amenities include: games, coffee maker, outdoor shower, lobster pot, cd player, wine glasses, fans, vacuum, washer &... View all property information
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    Oak Bluffs, Martha's Vineyard 02539
    1 / 13
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    About this property
    Our picture-perfect home is an excellent summer escape. Spacious double lot makes this setting seem like a parkland. It's just a 15-minute walk to downtown Oak Bluffs and the town beach. It's also on the public transit line and the bike path. View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 18
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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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 / 25
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Waterfront
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    About this property
    Adorable waterfront cottage, pristinely maintained throughout the years. Enjoy privacy and views from the spacious deck. 3 minute walk to great sandy lagoon beach - a perfect place for young children to play. Centrally located just 2 miles to either Vineyard Haven or Oak Bluffs town centers.... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 12
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Patio
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    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 / 20
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Leave your worries and your car behind, this picture perfect Vineyard beach house is steps from downtown Oak Bluffs, the sandy beach and a few short blocks from the ferry. Recently renovated and restored, four-bedrooms and one and a half baths, offering the perfect juxtaposition of cottage charm... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    1 / 15
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    All newly remodeled and furnished and tucked away on a quiet Oak Bluffs lane for the perfect reprieve after a day at the beach and shopping in town, along the Oak Bluffs harbor - and all just a short drive or bike ride away. This vacation home looks and feels so comfortable when you first walk in.... 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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    • Porch
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    • x
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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 / 14
    5 of 5 stars (2) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
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    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
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 14
    5 of 5 stars (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 / 20
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Pristine 4 bedroom waterfront hideaway. Enjoy spectacular views and sunsets across the lagoon. Private dock for boat enthusiasts. Kayak and boat rentals can be delivered to the property and kayaking on the lagoon is a fun and picturesque activity for the entire family. Centrally located, you are... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 23
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities and Features include... Hidden Cove, Centrally Located to Beaches and Towns, Association Tennis Courts, A/C, WiFi Additional amenities include: coffee maker, patio table and chairs, fans - portable, lobster pot, washer / dryer, landscaped, outside shower - enclosed, vacuum, outdoor... 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 / 20
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
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    • x
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    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
    1 / 10
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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 / 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
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    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 / 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
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    Oak Bluffs, Martha's Vineyard
    5 of 5 stars Reviewed 27 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 / 20
    5 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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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: nearby bank, close... View all property information
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    Oak Bluffs, Martha's Vineyard 02539
    1 / 11
    4 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    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
    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 02557
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    2010 newly renovated, features central AC, all new kitchen, 2 new baths and hardwood floors on the living level. Open kitchen, living and dining areas are flooded with light from the floor to ceiling windows and opens to a large wrap around deck with lovely views of the the lagoon. The master... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 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
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    3 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Walk to town and beach from this spacious modern home on a beautiful, treed lot. A delightful blend of amenities and charm. Central air conditioning. Amenities and Features include... Walk to Town, Central Air, WiFi Additional amenities include: beach chairs, coffee maker, patio table and... View all property information
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    Oak Bluffs, Martha's Vineyard
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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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
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    • Smoking allowed
    • x
    About this property
    This lovely 3 bedroom home features an open floor plan on the living level, colorful decor, window ac in all rooms and a well equipped modern kitchen. The home is nicely situated in quiet neighborhood, on the outskirts of Oak Bluffs, convenient to all three down island towns and beaches and a short... 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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    • Central Heating
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    • 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 02557
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Air Conditioning
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    • Pet-friendly
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    • x
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    • 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
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    Oak Bluffs, Martha's Vineyard 02539
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • x
    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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    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    This contemporary Cape, in a private setting, features a spacious, open, light, airy design with a wonderful large wrap-around deck. The bike path and MVTA (bus) are just a short ride/walk from the house. Two association tennis courts are an added plus! Additional amenities include: coffee maker,... 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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    • Air Conditioning
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    • Patio
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    • Child-friendly
    • 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
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    European-styled cottage is tucked away down a private lane surrounded by private yard with gardens - you’ll feel like you have completely gotten away from it all. The front door opens into a classic Mudroom with an antique wood, stadium bench seat - and then you step into the open and airy Great... 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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    • Parking
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    • Outdoor Dining Area
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    • Porch
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    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 02557
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • Smoking allowed
    • x
    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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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
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    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Families are sure to enjoy this cozy home with nautical inspired decor. The main living level offers a spacious living and dining area with cathedral ceiling cooled by window AC. and a neat well equipped kitchen with pass through window. The kitchen opens onto a spacious deck with patio dining and... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard