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Oak Bluffs Holiday Rentals

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    Travellers to Oak Bluffs are booking June dates now. Secure your holiday rental today, and have the perfect trip.
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    Oak Bluffs Contemporary Summer Home1 / 18
    (5)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Charming 3br Getaway in Oak Bluffs1 / 22
    (4)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Charming Farmhouse1 / 17
    (1)Excellent
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
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    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...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Charming 4 bedroom home in the east chop neighborhood of Oak Bluffs1 / 11
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Reviewed 7 September 2017
    My family had a wonderful time staying in this surprisingly spacious vacation cottage. It had a very home-y feeling to it, and plenty of room for all of us. The kids could...
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    About this property
    Adorable 4 bedroom cottage in the East Chop neighborhood of Oak Bluffs. You will love the beautiful back yard that has a patio and sizable garden and is very private. There is a large screened porch for entertaining. Inside are four comfortable bedrooms and two baths plus an outdoor shower. The...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • DVD Player
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    About this property
    New Renovated, 1870 historic 'Campground' cottage centrally located in Oak Bluffs, The cottage has 4 bedrooms (all located on the second floor) - 1 queen, 2 double beds and 2 twins beds. The front bedroom has its own balcony with water views. Cottage sleeps 8. the first floor includes a newly...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    About this property
    Classic Vineyard Oak Bluffs Cottage, tastefully and comfortably furnished. Large open deck on both the main and 2nd levels. Main living level features a lovely kitchen very well stocked with dining and cook items, main living room with TV and a large sunporch living area. Three lovely bedrooms, one...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    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...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    About this property
    Privately situated on a hilltop in Sengkontacket, -spacious tri-leve 4000 sq ft contemporary home. This wonderful vacation home has been updated for summer 2015, AC added, freshly painted, new carpeting and hardwood flooring and new furnishings. Set in a wonderful family friendly community offering...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Wonderful, spacious, lovingly maintained and attractive home in exclusive setting - family room with fireplace, large formal living room with fireplace, master bedroom with full private bath. Large kitchen and dining area that opens onto wonderful deck. Association tennis and boat landing on...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Waterfront
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    About this property
    Little Jaws, the home where the movie Jaws was filmed is a pristine beach cottage. Set in East Chop, this three plus bedroom rental offering features spectacular views, great swimming, kayaking and gorgeous sunsets. Relax on the large and comfortably furnished waterfront veranda. The living room...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    Outstanding vacation home, centrally located to all three down island town centers and multiple public beaches. Set in the Iron Hill Farm Community of homes this lovely home overlooks picturesque,- Little Duarte pond. Extended families will enjoy the multiple living spaces, 4 large bedrooms,- 3...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 1 Bathroom, Sleeps 6 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....
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 5 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    Cute and Cozy guest house with open floor plan in the kitchen, living and alcove sleeping area with queen bed. This cottage is perfect for couples, the owner will consider one additional child. There is a den with futon sofa separate from the main part of the cottage. Relax on the deck while you...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
    About this property
    Located just on the outskirts of Oak Bluffs and overlooking the lagoon this sweet summer home offers walking access to the lagoon for morning swims and is a great area for kayak enthusiasts. The sun filled interior features open living kitchen and dining area with a wall of glass that opens onto...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 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...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Tucked away among the shade trees on Martha's Vineyard, this delightful cabin in the woods is ideal for your next family vacation or getaway with a few close friends. This three-bedroom rental is located less than a mile from the top-ranked, semi-private Farm Neck Golf Club as well as the Trade...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    About this property
    Beautiful main house and guest located a short walk to a private association beach on Lagoon Pond. The main house has three bedrooms and the guest house has two bedrooms. The main house has nice open feeling with with cathedral ceilings in the living and dining room that opens to a lovely patio....
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    About this property
    Recently updated this lovely 4 bedroom, 3 bath contemporary home features an open floor plan in the living and kitchen areas opening to the covered porch and seating area on the front of the house and the deck and patio dining area off the back of the house. The main living room is centered around...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    6 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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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,...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 13
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    About this property
    Sitting on the 'summer porch' (that is what they were called in the days of old) sipping your favorite beverage, strolling the short distant to the water, relaxing around the table, Well equipped kitchen, reading in the living room with your feet these are possible when you stay in this well cared...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Beautiful, spacious, 4 bedroom 3.5 bath contemporary home set in a quiet lovely community on the outskirts of Oak Bluffs. This home comfortably hosts extended families with multiple living spaces. The main living level features an open concept and hosts a family TV room and luncheon breakfast nook,...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    About this property
    Families are sure to enjoy this cozy home with nautical inspired decor. The main living level offers a spacious living and dining area with cathedral ceiling cooled by window AC. and a neat well equipped kitchen with pass through window. The kitchen opens onto a spacious deck with patio dining and...
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    Oak Bluffs, Martha's Vineyard 02536
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    Wonderful Oak Bluffs home close to town and beach. This home has an open floor plan which is nice for relaxing with family and friends. Also enjoy the screened porch off the living area. Additional amenities include: coffee maker, outdoor shower, cd player, wine glasses, washer & dryer, ironing...
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    Oak Bluffs, Martha's Vineyard 02539
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    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,...
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    Oak Bluffs, Martha's Vineyard 02539
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    This charming home is situated in an idyllic private wooded setting on Sengekontacket Pond, one of the largest salt-water ponds on Martha's Vineyard. Comfortably furnished, it has a newlyr renovated kitchen and a new dining area overlooking Major's Cove. There is also a new screened in sun room for...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    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...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities and Features include... Meadow View Farms, Out of Town, Association Tennis, Hi Speed Internet Additional amenities include: coffee maker, fans - portable, lobster pot, food processor, washer / dryer, cd player, landscaped, outside shower - enclosed, outdoor furniture, tennis -...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Waterfront, Seaview Condo # 205 is a corner unit with balcony, spectacular waterviews and has been all newly updated for 2017 season. Perfect in town location just across the street from Inkwell Beach, walk to town center or pick up the bike path just a few hundred yards from the complex and bike...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Smoking allowed
    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...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    7 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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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...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 7 Bedrooms, 3 Bathrooms, Sleeps 14
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Views, Views and more Views! Lovely water views of Sengekontacket Pond over the rolling 'forever' conservation land. Large contemporary home has been recently updated to 4 bedrooms and 3 full baths. Large open living space with deck overlooking the view and sun room. Access to association dock and...
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    Oak Bluffs, Martha's Vineyard 02539
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    For those who love an in-town location this area known as the Campground with the historic Tabernacle is the ideal location. The sweet and colorful cottage is pristinely maintained by the owner. Rockers line the porch for your outside enjoyment. The main level hosts the living room with TV ( not...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    7 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    About this property
    Come and relax on the front porch of this lovely Vineyard home. Located in the desirable East Chop area of Oak Bluffs. The first floor has a nice open space with dining area and living room. There is a nice kitchen with everything you need to make family dinners. There is a bedroom and full...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 7 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    If you are looking for an immaculate, charming, cottage style, yet modern home and close to Oak Bluffs center look no further. This recently updated 3 bedroom, 2 bath home features sunny open living, kitchen and dining areas. Soft seashore color palette throughout adds to the ambiance of this great...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Spacious sun filled contemporary home located on a quiet private street,a 10 minute walk to town center, Inkwell Beach and harborfront, The first level features a spacious kitchen with stainless steel appliances, prep counter with range top. and breakfast nook, there is a comfortable living area...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    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 &...
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    Oak Bluffs, Martha's Vineyard 02539
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Smoking allowed
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    Beautiful Meadow View Farms home, bordered by expansive landscaped yard, peaceful private setting. Association tennis courts just a short distance from the house and Farm Neck Golf and Tennis is just a half mile from the house. Miles of connecting bike paths begin at the entrance to this lovely...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Charming six bedroom home located within walking distance to town. The first floor has a nice living room/dining area with doors that open to the front porch. There are two bedroom and one full bath on the first floor too. The second floor has four additional bedrooms and two bathrooms. There...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    OAK BLUFFS VICTORIAN ONE BLOCK FROM BEACH, TWO BLOCKS FROM TOWN!1 / 22
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    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    About this property
    This well maintained, vintage Victorian home is centrally located, yet away from the hustle and bustle of town: just one block from the beach, two blocks from Waban Park and Ocean Park, three blocks from tennis, backetball and a playground and four blocks from town. Enjoy the waterview of Vineyard...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    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....
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Modern two bedrooms, one bath cottage situated at the end of a quiet street. This cozy cottage is Oak Bluffs center and the town beaches. The home has recently been renovated with new comfortable furnishings including linens and mini spit air located about one mile to shops, restaurants in...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Four bedroom Oak Bluffs home located in the Waterview Farm area of Oak Bluffs. Adjacent to Farm Neck Golf & Tennis. Access to Sengekontacket pond. Great for kayaking and canoeing. Large house great for an extended family or two small families. The first floor has an open concept living room,...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    6 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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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...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 10
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    6 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Smoking allowed
    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...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 10
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    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...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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....
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Oak Bluffs, Martha's Vineyard 02536
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 8
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