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Holiday Homes and Apartments Oak Bluffs, MA

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    Travellers to Oak Bluffs are booking August dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 16
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | 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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    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • Washer
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    • Ocean Views
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    About this property
    This fabulous 125 year-old Victorian cottage was lovingly updated and completely restored in 2012. Sitting on a large private lot, just steps from Inkwell beach, Solera offers the perfect balance of comfort, ambiance and vintage charm. The large, airy gourmet kitchen was featured in This Old House... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 19
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    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
    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 / 23
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Views, Views and more Views! Lovely water views of Sengekontacket Pond over the rolling "forever" conservation land. Large contemporary home has been recently updated to 4 bedrooms and 3 full baths. Large open living space with deck overlooking the view and sun room. Access to association dock and... View all property information
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    Oak Bluffs, Martha's Vineyard 02539
    1 / 21
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
    1 / 21
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Sea Glass Cottage Martha's Vineyard Vacation Rentals Sleeps 6. Completely renovated, this charming East Chop cottage will allow its guests to experience all the comforts of modern luxury living combined with the historical splendor of many reclaimed antique furniture pieces from Martha's Vineyard... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
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    Oak Bluffs, Martha's Vineyard
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    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 / 16
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities and Features include... Central Air, Additional amenities include: coffee maker, lobster pot, food processor, 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
    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 / 14
    4 of 5 stars (1) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Come experience the magic of the Vineyard in our island home. Modernized in 2011, this charming residence is clean, cozy and boasts new furniture and decor. Amenities include 3 TV’s, cable television, Wi-fi, DVD, telephone, I-home, and Keurig Coffee maker. The property has a private yard, sundeck,... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 25
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    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
    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
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Terrace
    • Balcony
    • Satellite TV
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Private Garden
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    • x
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    • x
    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 / 31
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Waterfront
    • Satellite TV
    • Private Outdoor...
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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 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
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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 / 16
    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
    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Waterfront
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    • x
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    About this property
    Lovely two bedroom, 2 bath condo unit with sweeping water views. Town center is but a 5 minute walk from the condo complex where you will find, family and fine dining, shops. groceries, the famous Flying Horse Carousel,- a great attraction for children and the young at heart. Stroll along the... 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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    • x
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    • x
    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
    1 / 18
    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • x
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    About this property
    Our comfortable, reverse contemporary home has 2 bedrooms on the first floor (one with a full size bed and one with a twin), a 3/4 bath with shower, as well as a family room with a fold-out futon couch. Upstairs on the second floor, our home has an open design with a bright kitchen/dining/living... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    5 of 5 stars Reviewed 14 April 2016
    Location, location is perfect for getting to town, beach and other parts of MV! The house is right size for family of 4. The owner is very responsive and the house was well...
    5 of 5 stars Reviewed 20 August 2015
    I most say this house had everything we needed. Perfect for a small family getaway. Location being prime not even a mile from downtown. My family absolutely had a blast. I plan on...
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    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    A new Cape style residence situated on a wooded lot near bike path and just a short ride to town center and ferry. This home features an open design with a bright kitchen/dining/living area with hardwood floors, den and full bath on the first floor. Sliders in the dining area lead out onto a nice... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 18
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Spacious contemporary 4 bedroom 3.5 bath home located in one Oak Bluffs most exclusive neighborhoods. This house offers many features such as hardwood floors, central air conditioning, and a large living dining area with walk out deck and patio. The yard is nicely landscaped with waterviews over... View all property information
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    Oak Bluffs, Martha's Vineyard 02539
    1 / 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 / 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 / 18
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Enjoy the charm of a Vineyard cottage with all the amenities of today. This 3 bedroom house has brand new furnishings for 2015. It is in a quiet neighborhood not far from Oak Bluffs center and its harbor. The house is also close to the bike path. The house has an open floor plan with a large... View all property information
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    Oak Bluffs, Martha's Vineyard 02539
    1 / 23
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Sitting on the "summer porch" (that is what they were called in the days of old) sipping your favorite beverage, strolling the short distant to the water, relaxing around the table, Well equipped kitchen, reading in the living room with your feet these are possible when you stay in this well cared... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 22
    7 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Classic, "Camp Ground" over sized 7 bedroom 3 bath home in a residential neighborhood within easy walking distance to the beach, shops, restaurants, galleries, etc. It offers double master bedrooms (1st and 2nd floor.) Enjoy rocking on our huge front porch in over sized Georgia rockers. As you... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    6 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
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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 02557
    1 / 43
    6 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    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
    1 / 16
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    About this property
    New for the 2016 season! Enjoy this wonderful new three bedroom three and half bath home in Oak Bluffs. The first floor has an open concept with a beautiful chefs kitchen, large dining room and family room with TV. The first floor also has a master bedroom en suite with a king size bed and TV.... 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
    Set in one of the Island's loveliest planned residential areas with beautiful landscaping, overlooking Sengekontacket Pond. Wonderful pond views from all bedrooms and living area. This spacious three floor house is well maintained and attractively decorated. Full deck across back facing pond.... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 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 / 13
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • x
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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 / 37
    7 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • x
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    About this property
    Large families looking for a true shore experience will enjoy this delightful,whimsical, large historic summer home with cottage details set on the edge of Harthaven Harbor. The home boasts spectacular views of Vineyard Sound from all areas of the home. Private path leads you to a pristine private... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 27
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    MVVR EXCLUSIVE: Custom crafted tri-level, this beautiful sun filled home features, spacious open living spaces, hardwood floors throughout, sleeps 8 with 2 King Masters en-suite, guest king bedroom and semi-private Alcove sleeping area on the 2nd level ( see photo 23) Exterior features include two... View all property information
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    Oak Bluffs, Martha's Vineyard
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    5 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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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 / 12
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Patio
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    • Porch
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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 / 18
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    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
    1 / 30
    5 of 5 stars (1) Excellent
    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    • Waterfront
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    • Pet-friendly
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    • x
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    • x
    About this property
    Located on over 1 acre of waterfront property on East Chop, an exclusive area of historic Oak Bluffs, this unique home is perfect for family and friends that want to vacation together while maintaining their privacy. This home allows up to 4 families to stay together in the same home while giving... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 19
    5 of 5 stars (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • Air Conditioning
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    • x
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    • x
    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
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    Oak Bluffs, Martha's Vineyard
    5 of 5 stars Reviewed 29 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 / 15
    3 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    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
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Central Heating
    • Parking
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Home away from Home! Walk to Sailing Camp! Bright, sunny 3 bedroom Cape style vacation home in Lagoon Heights with great amenities. Fully furnished home with 2 baths, outdoor shower, large deck and private enclosed yard and a wonderful deck for the summer cookouts. Open floor plan with spacious... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 22
    4 of 5 stars (1) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Grill
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    • Hot Tub
    • Porch
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    • x
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    • x
    About this property
    Walk to town from this meticulously maintained, large & airy, 3 bedroom, 3 full bathroom vacation getaway, located on a beautiful 1/4 acre lot on a quiet street. Watch your troubles sail away while relaxing on the large farmer's porch with your favorite summer beverage, or grilling with family and... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    European-styled cottage is tucked away down a private lane surrounded by private yard with gardens - you’ll feel like you have completely gotten away from it all. The front door opens into a classic Mudroom with an antique wood, stadium bench seat - and then you step into the open and airy Great... 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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    • x
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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
    6 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • DVD Player
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    • Patio
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    • Satellite TV
    • Waterfront
    • Porch
    • Secure Parking
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Historic summer "cottage" with 7 bedrooms, sleeping porches, a deck overlooking the water, a private dock on Harthaven Harbor, and immediate access to the ocean. The rustic home is a perfect gathering spot for family and friends. It has a large living room with a huge stone fireplace, an eat-in... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02557