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Holiday Rentals and Villas in Chilmark, MA

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    Travellers to Chilmark are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 10
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    4.5 of 5 stars (4) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    1 / 9
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    1 / 8
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Main House on the same property may be occupied by Owner or another Tenant. Peaceful private setting on one of the most beautiful areas on the South Shore. Amenities and Features include... Waterfront Guest House, Private Beach Additional amenities include: coffee maker, patio table and... View all property information
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    Chilmark, Martha's Vineyard
    1 / 25
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Gorgeous Views of Stonewall Pond from this immaculate 4 bedroom three bath home. Cathedral ceilings add to the spacious feeling of this contemporary home and the open kitchen, living and dining areas provide the perfect space for your summer vacation. There is a spacious loft area that opens to the... View all property information
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    Chilmark, Martha's Vineyard
    1 / 18
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Contemporary Post and Beam home, private location, bounded by large oaks and stone walls. Enjoy this impeccably maintained 3 bedroom, 3 bath home. Custom designed and featuring a chef's kitchen. The cathedral ceiling great room is open to the spacious dining and kitchen area. Custom features... View all property information
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    Chilmark, Martha's Vineyard
    1 / 13
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Amenities and Features include... Menemsha, Waterview, Walk to beach Additional amenities include: coffee maker, fans - portable, lobster pot, food processor, washer / dryer, cd player, outside shower - enclosed, vacuum, outdoor furniture, ironing board. View all property information
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    Chilmark, Martha's Vineyard
    1 / 21
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Immaculate waterfront gem on Stonewall Pond. Breathtaking views across pond to barrier beach. Perfect for honeymoon getaway. Sleeps four - please ask agent for details. Walk or kayak to Stonewall Beach. Pets Considered. Amenities and Features include... Waterfront, Hi Speed Internet Additional... View all property information
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    Chilmark, Martha's Vineyard
    1 / 14
    1 Bedroom, 2 Bathrooms, Sleeps 3 | Quick View
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    About this property
    'The Little House' on the beach. Two minute stroll to South surf beach. Incredible views from sunrise to sunset. Private tennis courts shared with owners and other tenants. Access to Stonewall Pond for launching canoes and kayaks. This wonderful cottage is a one of a kind. A pet will be considered... View all property information
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    Chilmark, Martha's Vineyard
    1 / 10
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    High in the hills of peaceful Chilmark with distant panoramic waterviews, this four bedroom impeccably maintained house with in gound pool is surrounded by beautifully landscaped grounds. Expansive decks invite you to make the most of summer living. Amenities and Features include... Chilmark,... View all property information
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    Chilmark, Martha's Vineyard
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    1 / 15
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Amenities and Features include... North Slope Hilltop House. Private yard, Screeen Porch and Patio, All new AC Throughout, 8 minute drive to Lucy Vincent Beach or Menemsha Village Additional amenities include: coffee maker, patio table and chairs, fans - portable, lobster pot, washer / dryer, cd... View all property information
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    Chilmark, Martha's Vineyard
    1 / 11
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Spacious, well furnished and equipped, comfortable home in quiet neighborhood on 3 acres. Two master bedrooms, one on each floor; pool table. Within walking distance (about 1 mile) to small North Shore beach (Great Rock Bite). Three mile drive to Lucy Vincent Beach. Amenities and Features... View all property information
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    Chilmark, Martha's Vineyard
    1 / 24
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Casual immaculately clean in picturesque Menemsha, Chilmark waterfront. Beautiful views. A short stroll to the beach, fish market, boutiques, fishing, and shore dinners. Guest House - Main House on property nearby may be occupied by Tenants or Owner. Amenities and Features include...... View all property information
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    Chilmark, Martha's Vineyard
    1 / 18
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Panoramic South Shore ocean vista from this outstanding private rental home. Less than one mile to famous Lucy Vincent Beach. Owner also offers private beach rights to the south side via canoe or kayak (provided by owners.) Classic style and modern luxury combine to make this family retreat a very... View all property information
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    Chilmark, Martha's Vineyard
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Pristine modern summer cottage with distant views of Lucy Vincent Beach, privately nestled on historic Eddy Farm, hillside, off of South Rd. This light filled home with acres of privacy is the perfect retreat for those looking for a long term summer stay in Chilmark with Lucy Vincent Beach just a... View all property information
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    Chilmark, Martha's Vineyard
    1 / 33
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    Pristine renovated barn set on acres of extreme privacy with ocean views and private ocean beach. This is an extraordinary residence with exposed beams and glass walls framing expansive views of meadows and the Atlantic ocean beyond. The refined interior offers open living spaces, large dining area... View all property information
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    Chilmark, Martha's Vineyard
    1 / 33
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Steps from Menemsha Pond – look across the ever-changing surface of the water to Menemsha, the Creek, the Lobsterville dunes, Vineyard Sound and the Elizabeth Islands. Magnificent sunsets from the living room. This cathedral-ceiling Modernist masterpiece is constructed entirely of Western red... View all property information
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    Chilmark, Martha's Vineyard
    1 / 25
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Tastefully furnished and decorated with antiques and art. This Chilmark summer home is an original Yankee Barn located off South Road that has all the accouterments for summer entertaining. The post and beam structure features a beautiful cathedral living room brightened by southern light; has... View all property information
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    Chilmark, Martha's Vineyard
    1 / 39
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Stunning Waterfront Views. Kayak or swim across the pond to Stonewall Beach or just relax on the expansive decks overlooking the water. This is an immaculate updated home with waterviews from just about every room and, is tastefully furnished, features a chef's kitchen 3 bedrooms, - master ensuite... View all property information
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    Chilmark, Martha's Vineyard
    1 / 30
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Outdoor Dining Area
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    • x
    About this property
    Come enjoy the secluded beauty of this award-winning, architect-designed home in Chimark on almost four acres of land. Relax on the two level deck or on the beach at Lucy Vincent, Squibnocket, or nearby Menemsha. The remarkable design makes great use of over 3500-square-foot space by joining the... View all property information
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    Chilmark, Martha's Vineyard
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    1 / 22
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    Charming 4 bedroom, 3 bath traditional summer cottage. Enjoy this impeccably maintained summer home surrounded by a mature landscaped yard with lots of flowering shrubbery. A large deck offers privacy and a wonderful setting for those summer barbecues. A modern well equipped kitchen opens to the... View all property information
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    Chilmark, Martha's Vineyard
    1 / 6
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    Enjoy the in ground pool and spectacular ocean views from this casual, mostly glass hill top contemporary. Kick back and relax by the pool in an area of splendid nature. Amenities and Features include... Spectacular Waterviews, Pool, WiFi Additional amenities include: coffee maker, pets... View all property information
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    Chilmark, Martha's Vineyard
    1 / 23
    6 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • x
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    Contemporary Home commands one of Martha's Vineyard's most spectacular views overlooking the Elizabeth Islands and Vineyard Sound. Breathtaking sunsets. Outdoor patios and deck and multiple living areas provide many options for family gatherings or quiet times. Amenities and Features include...... View all property information
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    Chilmark, Martha's Vineyard
    1 / 14
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    About this property
    Sweeping water view over Vineyard Sound to the Elizabeth Islands. Freshly renovated Cape-style, three bedrooms, with sofa beds in den and sunroom, sleeps 8-10 people. Short walk to lovely Menemsha Village, and less than two miles to Lucy Vincent's Beach. Large, landscaped treed lot of 2.3 acres on... View all property information
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    Chilmark, Martha's Vineyard
    1 / 31
    5 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    MVVR EXCLUSIVE: Spectacular 5 bedroom, 4.5 bath retreat. Lovely distant waterviews overlooking the South Shore. Hilltop setting with privacy and a five minute drive to Lucy Vincent Beach. This spacious custom home has been decorated by one of the island's premier professionals. A combination of... View all property information
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    Chilmark, Martha's Vineyard
    1 / 12
    2 Bedrooms, 1 Bathroom, Sleeps 3 | Quick View
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    • x
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    • x
    About this property
    Great location. Menemsha Village. 2 bedroom cottage. Sunny interior. 1 bath, plus outdoor shower. Storage barn, cable tv, High Speed internet, washer. Walk to beach, harbor, dock, stores, restaurants. Currently available August only. $1595 per week. 2 wk minimum. Maximum occupancy 2 adults,... View all property information
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    Chilmark, Martha's Vineyard
    1 / 12
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Charming recently renovated summer cottage features large open living room with sliders leading on to a screened porch and private deck beyond. Porch is fully furnished for dining and relaxing, providing aditional outdoor living space. The deck is private and surrounded by the yard area. The house... View all property information
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    Chilmark, Martha's Vineyard
    1 / 10
    4 of 5 stars (1) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Situated on a cul-de-sac overlooking a private meadow with spreading oaks ensures privacy. The screened porch, meadow bench, hammock and second floor deck off the master bedroom provide quiet spots to get away. Amenities and Features include... Wifi, A/C in Master Additional amenities include:... View all property information
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    Chilmark, Martha's Vineyard
    4 of 5 stars Reviewed 11 August 2014
    Great vacation. Home was clean, property is private and quiet and as always, very comfortable. Convenient location for our family vacation needs. Lack of recycling at house...
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    1 / 21
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    An award winning architectural design coupled with Vineyard charm and seclusion, this house has two wings allowing for multiple family co-existance. This vacation home is open, spacious and filled with light with a wrap-around deck for sun or shade. Amenities and Features include... Additional... View all property information
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    Chilmark, Martha's Vineyard
    1 / 26
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    You'll be all atwitter about the Bird's Nest at Chilmark Pond. Gather your family or friends and enjoy this Martha's Vineyard vacation home, with ocean views, during a June getaway. Whether you bring your own watercraft or rent from the home-delivery service, Book-a-Boat, you can launch from the... View all property information
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    Chilmark, Martha's Vineyard
    1 / 20
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Set on 5 acres of woods and meadow. A small farm setting with chickens and pigs and a garden for you to enjoy. Be a farmer for a week, without the work! Our hens lay eggs that you can collect every morning. The pigs love your dinner scraps and we invite you feed them if you wish. The animals are... View all property information
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    Chilmark, Martha's Vineyard
    1 / 33
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Island Romance is a Chilmark vacation rental with ocean views on a quiet plot of land, featuring a shared dock, spacious yard, and studio cottage. Bring your friends and loved ones to this sweet New England farmhouse on Martha's Vineyard. In summer you'll be able to use the home's semi-private dock... View all property information
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    Chilmark, Martha's Vineyard
    1 / 37
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    With old-world charm aplenty and modern amenities, you'll enjoy a relaxing holiday at this Chilmark vacation rental. It's a great spot for a family looking for a quiet refuge. You're near the center of town and close to iconic businesses, but you're also not far from the cliffs at Aquina as well as... View all property information
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    Chilmark, Martha's Vineyard
    1 / 34
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    About this property
    Dramatic ocean views, idyllic one of a kind location in gated community, private ocean beaches are but a few of the desirable features of this all new 5 bedroom, 5 bath contemporary home, set in one of the most Idyllic landscapes on Martha's Vineyard. Situated hilltop this gorgeous summer home... View all property information
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    Chilmark, Martha's Vineyard
    1 / 38
    Studio, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    About this property
    Expansive views of Chilmark Pond and the Atlantic Shoreline. Deeded access to pond, dock and private ocean beach (please inquire for more information). Newly completed 5400 square foot luxury home with ... multiple decks overlooks the masterfully landscaped grounds, stone walls, and ocean views... View all property information
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    Chilmark, Martha's Vineyard
    1 / 29
    4 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    This incredible home is furnished with one of a kind artisan wood and textile pieces, as well as Donghia soft seating and is filled with art, vintage stain glass, antiques, and one of kind artisan furniture. The ocean view is spectacular from the great room (living room, dining area and kitchen,... View all property information
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    Chilmark, Martha's Vineyard
    1 / 19
    5 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Classic coastal cottage remodeled in 2000. Charming open and sunny interior feautres 3 bedrooms and 2 baths in the main house. 2nd level Master bedroom opens onto private deck with views of Menemsha Harbor. Seperate guest cottage has Queen bed and a full bath. Outdoor spaces for your vacation... View all property information
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    Chilmark, Martha's Vineyard
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Lovely 3 bedroom 2 bath home. All new kitchen and baths. Completely renovated - lots of glass for a light filled interior. This lovely home in a private setting is surrounded by mature Holly trees, Laurel and attractive native shrubs. 1 mile to Alley's General Store. 10 minute drive to Lucy Vincent... View all property information
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    Chilmark, Martha's Vineyard
    1 / 22
    5 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Ocean Views
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    • x
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    About this property
    Enter our vacation world up a 0.2 mile paved driveway through the woods to the private hilltop with only two other houses. Open the gate and delight at the expanse of ocean view from the deck over oak trees - our 3 1/2 acres adjacent to a sanctuary seem like 100. Listen to the birds and the surf... View all property information
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    Chilmark, Martha's Vineyard
    1 / 26
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    This quintessential Chilmark home has been impeccably maintained and continuously updated. The dining and living areas open to a wrap around deck. Enjoy spectacular water views and sunsets from just about every room in the house. Stroll to the beach and Menemsha village where you will find the fish... View all property information
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    Chilmark, Martha's Vineyard
    1 / 34
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • Patio
    • Porch
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Outstanding private rental home nestled on 7.5 private acres in the seaside community of Chilmark on the Island of Martha's Vineyard, features a key to Quansoo Beach, one of the most beautiful private association beaches on the island. Warmth, comfort and charm await you and your family in this... View all property information
    Location Information
    Chilmark, Martha's Vineyard
    1 / 18
    5 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    Amenities & Details
    • Internet Access
    • Satellite TV
    • DVD Player
    • Grill
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Reverse Contemporary Five Bedroom home just minutes to Menemsha. There are open living spaces with living room , dining room and kitchen that open to deck with waterviews of the North Shore. Just a short drive to famous Lucy Vincent Beach, Chilmark Store, library and Community Center. Walk to a... View all property information
    Location Information
    Chilmark, Martha's Vineyard
    1 / 11
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • DVD Player
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Immaculate 4 bedroom in a private setting yet just a 10 minute drive to town or the most beautiful Lucy Vincent Beach. Features include large deck and wifi internet. The house has an open floor plan and an additional family/tv room for your comfort. Amenities and Features include... Large Deck,... View all property information
    Location Information
    Chilmark, Martha's Vineyard
    1 / 13
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    Amenities & Details
    • Central Heating
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Clean and family friendly. Centrally located, the cottage is only fifteen minutes from most island towns including Edgartown and Aquinnah, where dining and shopping are world renowned. Lovely wooded setting offers privacy with large comfortable deck and yard. Outdoor shower adds to the Vineyard... View all property information
    Location Information
    Chilmark, Martha's Vineyard
    1 / 23
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Internet Access
    • Grill
    • Satellite TV
    • DVD Player
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    The house is magnificently located atop a slightly sloping knoll overlooking Stonewall Beach in Chilmark, and on Stonewall Pond. Property benefits include access to the family tennis court, access to the flotilla of kayaks and paddle boards on the Pond, and private access to the Stonewall Beach,... View all property information
    Location Information
    Chilmark, Martha's Vineyard