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Holiday Homes and Apartments Oak Bluffs, MA

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    1 / 23
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    7 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    4 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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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... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 19
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    About this property
    This unique and elegant four bedroom beach cottage is situated on the north shore of Martha's Vineyard. For your relaxation, there is a large porch/patio leading out to the beach affording magnificent views. Additional views from the tastefully decorated living area, bedrooms areas, make this a... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 10
    4 of 5 stars (1) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Spacious, immaculate 4 bedroom, 3 bath home. Large deck for outdoor enjoyment. Situated just outside the busy center of Oak Bluffs. It is a 10 minute walk to all activities, dining, movies and beach, historic Campground Ginger Bread cottages. There are walkways all the way into town. Amenities... 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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    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, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Pristine 4 bedroom waterfront hideaway. Enjoy spectacular views and sunsets across the lagoon. Private dock for boat enthusiasts. Kayak and boat rentals can be delivered to the property and kayaking on the lagoon is a fun and picturesque activity for the entire family. Centrally located, you are... View all property information
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    Oak Bluffs, Martha's Vineyard
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Stylish Cape located close to town and beach.attention to detail in every room. Relax and enjoy all the comforts of home in this all new pristine 3 bedroom, 2 bath home. The main living level features an open kitchen living and dining with AC. In additon there is separate TV room with office area... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 14
    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... View all property information
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    Oak Bluffs, Martha's Vineyard
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    1 / 20
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Spectacular water view in desirable East Chop neighborhood. This 4 bedroom, 3 bath home is just 1.5 miles from Oak Bluffs Center and Beach. There is a yard with multiple decks and waterviews. Features include central air and wifi internet. Beautifully decorated. Amenities and Features include...... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 10
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Cozy guest house sleeps 4. Open floor plan with queen bed alcove off of living room. One bedroom with one set of bunk beds. Large deck with view of Lagoon. Owner or guests occupy main house. Amenities and Features include... Lagoon Guest House, Walk to Private Lagoon Beach Additional amenities... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 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
    1 / 7
    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • Outdoor Dining Area
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    About this property
    A comfortable ranch with all the amenities for a perfect vacation. It's quiet location is 1.5 miles from town, yet not too far to bike or walk in when needed. Beaches, ponds, the lagoon, and other recreational facilities are also easily accessible if you want to hop on the bike path around the... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 12
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
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    • Waterfront
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    About this property
    This cozy, quaint waterfront property offers beautiful sunsets and great harbor views. Swimming, boating, kayaking, are just steps from this warm and charming quintessential Vineyard cottage. Amenities and Features include... Waterfront, Waterview Additional amenities include: dock/boat-slip,... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 18
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Please note - all new master bedroom and bath completed in 2014 (not shown in photos) Amenities and Features include... Sengekontacket, Central Air Additional amenities include: coffee maker, patio table and chairs, lobster pot, food processor, washer / dryer, cd player, landscaped, outside... View all property information
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    Oak Bluffs, Martha's Vineyard
    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 / 19
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Picturesque ocean views across Farm Pond to Vineyard Sound. Walk to beach and town. Bike path is one block away from this beautifully renovated three bedroom, two bathroom home. Open, airy with lots of glass. The dining and living areas open to deck. Amenities and Features include... Farm Pond... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 27
    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... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 13
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    Bright and newly remodeled classic summer cottage. Conveniently located just one mile from Oak Bluffs town center, Ink Well Beach, shops, fine and family dining, historic Flying Horses Carousel, public tennis courts, Bandstand Park and Oak Bluffs Harbor-front area. The professionally landscaped... View all property information
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    Oak Bluffs, Martha's Vineyard
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    1 / 61
    5 of 5 stars (1) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 22 | Quick View
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    • Hot Tub
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    About this property
    This upscale, newly renovated, 4 bedroom home in a quiet neighborhood in Oak Bluffs. You are 2.5 miles from the town center and Inkwell and State beautiful public beaches. This home boasts a large unground back yard pool and hot tub on the mahogany deck. Large outdoor shower. Grill and fire pit... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 33
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    A recent renovation has moved this home to the top of the list in terms of comfort in a tastefully decorated waterfront home. A new family media room has been added giving extended families lots of space to relax. The open concept kitchen, dining and living areas feature waterviews and open onto a... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 20
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Waterfront
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    • x
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    • x
    About this property
    Beautiful waterfront home with central A/C, features open floor plan and sunny living spaces. The great room has two distinct seating areas and is equipped with a flat screen TV. There is a formal dining room set between the living area and kitchen and opens to the outdoor patio with gorgeous... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 9
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
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    • Secure Parking
    • Balcony
    • Wi-Fi
    • Ocean Views
    • Terrace
    • Private Garden
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    • x
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    • x
    About this property
    This is an original Pratt house built in 1866 by the famed architect Pratt for whom the Pratt Institute in New York was named. It is located in the historic district across from a large park in which baseball, golf practice, kite flying, bike riding, picnics and even, on at least one occasion,... View all property information
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    Oak Bluffs, Martha's Vineyard
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    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
    1 / 11
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    Walk to Oak Bluffs town center or Inkwell beach from this fabulous beach-chic cottage with all new furnishings in 2014. Open floor plan with high ceilings, but cozy and comfortable. Two bedrooms upstairs both with Queen-sized beds. Full bath downstairs with front-load washer/dryer. Modern,... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 13
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    Families are sure to enjoy this cozy home with nautical inspired decor. The main living level offers a spacious living and dining area with cathedral ceiling cooled by window AC. and a neat well equipped kitchen with pass through window. The kitchen opens onto a spacious deck with patio dining and... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 24
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Custom built with extraordinary attention to detail. Located on Lagoon Pond with panoramic views up the lagoon. Large comfortably furnished deck and screened porch with dining create a most relaxing atmosphere overlooking the water. Luxury features throughout the house not seen in most rental... View all property information
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    Oak Bluffs, Martha's Vineyard
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    6 Bedrooms, 2 Bathrooms, Sleeps 11 | Quick View
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    About this property
    Amenities and Features include... In-Town, Walk to Beach, Wifi Internet Additional amenities include: coffee maker, patio table and chairs, fans - portable, lobster pot, washer / dryer, cd player, landscaped, outside shower - enclosed, outdoor furniture, ironing board. View all property information
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    Oak Bluffs, Martha's Vineyard
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    8 Bedrooms, 8 Bathrooms, Sleeps 20 | Quick View
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    • x
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    About this property
    Amazing five acre property! 6 BR main house w/ pool + a 2 BR carriage house! Our amazing property is perfect for everything from a memorable family vacation to a serene retreat. You and your guests will begin to enjoy the feeling of privacy the minute you arrive as you drive down the long tree... View all property information
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    Oak Bluffs, Martha's Vineyard
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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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... View all property information
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    Oak Bluffs, Martha's Vineyard
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    5 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    About this property
    Penacook 5 Bedroom Cottage - short stroll down one of the nicest streets in Oak Bluffs to the beach in one direction and town center in the other, where you will find shops, eateries,- gourmet and family style, entertainment, the historic Flying Horsed Carousel, and the beautiful harborfront area.... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 20
    5 of 5 stars (56) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • ?
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    • x
    About this property
    This Oak Bluffs, Martha's Vineyard rental is a certified National Historic Property. Ideal location for visitors in the middle of the most active, multi-cultural, charming, and fun town on Martha's Vineyard. Step outside your door for breakfast or ice cream, a great selection of restaurants in... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 10
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities and Features include... Private Pool, High Speed Internet Additional amenities include: coffee maker, patio table and chairs, fans - portable, 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
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    6 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Beautifully upgraded 5 1/2 Bedrooms 2 1/2 Bath, Formal Dining room, and a Veranda! Spacious outside deck for family, friends and Fun! Less than a block away from the beautiful beach and a leisurely walk to town. Weekly rental on Season ( July thru August) Saturday to Saturday. (May and September a... View all property information
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    Oak Bluffs, Martha's Vineyard
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This airy home captures the spirit of easy island life and makes you feel like you've gotten away. It's secluded on a quiet, wooded, paved, dead-end street, the second house from the end. Yet it's centrally located in the East Chop area of Oak Bluffs for easy access to the beaches (.25 miles to... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 10
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This gorgeous, contemporary air-conditioned private home is perfect for your luxurious vacation on the island. It is 2700 sq ft of well laid-out space and sits on 1.4 acres of land in a private wooded area, centrally located, only minutes from downtown Oak Bluffs and beautiful beaches. The... View all property information
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    Oak Bluffs, Martha's Vineyard
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • x
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    About this property
    This beautiful fully renovated cottage beach house is available for weekly rent. Come enjoy the great ocean views. Sit out on the large front covered porch - enjoy friends, family and great times! Relax to the sights and sounds of the beautiful ocean. House comfortably sleeps 10 and includes a... View all property information
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    Oak Bluffs, Martha's Vineyard
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    A fully renovated four bedroom home with 3 1/2 baths, family room, landscaped lot and a private beach and dock. Dock can accommodate up to a 25 foot motor boat, located on The Lagoon and is accessible to Vineyard Sound. Family room has cable TV, deck, fully equipped kitchen, and a 2 person kayak... View all property information
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    Oak Bluffs, Martha's Vineyard
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    5 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Smoking allowed
    • x
    About this property
    Across the street from the renowned Inkwell beach and just minutes to walk to town, harbor and the ferry. This large classic victorian beach house was built in 1851. The property has a beach studio next door which can be rented for larger groups. A large classic wrap around porch with ocean... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    1 / 30
    4 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    • Balcony
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Secure Parking
    • Private Outdoor...
    • Washer
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    New to the 2015 Summer Season! This spacious waterfront home offers 4-bedrooms en-suite, with family, game and fitness rooms...and yes, a pool. The peaceful setting is centrally located, yet close to the village center for easy access to shops, restaurants and more. The home is tastefully... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    1 / 29
    5 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • Parking
    • Internet Access
    • Patio
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    It's all about the stellar location of this five-bedroom Oak Bluffs getaway, a wonderfully renovated Victorian home with a front porch and deck, four bikes to help you explore Martha's Vineyard, and an enclosed yard that is ideal for kids. This two-level house sits just half a mile from the... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    1 / 32
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Relax in optimal comfort at this Oak Bluffs home. It's got four bedrooms and lots of space for an ideal family vacation! You're in the heart of Oak Bluffs, within walking distance of the harbor and lovely waterfront. You can hop off the ferry to Martha's Vineyard and be here in no time. This... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    1 / 24
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Internet Access
    • Patio
    • Grill
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Escape to the perfect island getaway at this gorgeous, recently renovated Oak Bluffs home on lovely Martha's Vineyard. Light-filled bedrooms, a playroom, and a huge deck await! Downtown Oak Bluffs is nearby and it's only one mile to the water. If you'd rather remain on the property, you're... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    1 / 33
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • DVD Player
    • Satellite TV
    • Waterfront
    • Grill
    • Internet Access
    • Air Conditioning
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Historic harborfront home with private dock has been completely renovated and newly furnished, beautifully appointed throughout to reflect summer living on the Vineyard. The large living and dining areas open onto the expansive and comfortably furnished porch, overlooking picturesque Oak Bluffs... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    1 / 30
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Internet Access
    • Satellite TV
    • DVD Player
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Summer Dream offers the opportunity for a relaxing vacation in a beautiful environment. This 4 bedroom, 2 ½ bath home has a beautiful new kitchen and new living room furnishings including a 56' LED television. Summer Dream is in the lovely Hidden Cove neighborhood adjacent to Sengekontacket Pond... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    1 / 23
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • DVD Player
    • Grill
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Quietly nestled on quiet street just on the outskirts of town, this brightly lit home features a mix of coastal details and traditionally styled upscale furnishings for your comfort. The interior has open floor plan that flow nicely to outdoor living spaces including a screened porch and brick... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 18
    5 of 5 stars (5) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Washer
    • Parking
    • Outdoor Dining Area
    • Grill
    • DVD Player
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This spacious condo is an ideal vacation rental for a small family, a couple or two couples looking for clean, comfortable accommodations with the amenities needed to ensure a relaxed vacation. This large 2 bedroom end unit (1200 sq ft + large deck) is bright and airy. Downstairs has new hardwood... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    1 / 36
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Patio
    • Grill
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Oak Bluffs retreat featuring three levels of luxury living, professionally decorated by one of the islands premier decorators This house is privately situated in an enclave of lovely homes. Bike paths at the entrance connect to miles of biking trails. Farm Neck Golf Course and Restaurant are just a... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Amenities & Details
    • Patio
    • Parking
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Stay in this peaceful, well-maintained home with a large wrap-around porch, a deck, and in close proximity to the ocean for your next unforgettable New England vacation. Come with a small group of friends, bring your own small family, or get away with another couple and rest assured that you'll... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard