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Chilmark Vacation Rentals

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    Travelers to Chilmark are booking June dates now. Secure your vacation rental today, and have the perfect trip.
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    3 Bedrooms, Sleeps 6Quick View
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, Sleeps 6Quick View
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    About this property
    Lovely rural home near farms, yoga studio. Across from preservation land with hiking trail. Walk to Grange Hall, Farmer's Market, general store and cafe. ( 2000 ft² ) New master suite in pleasant cottage style home. Grassy yard and small garage. Isolated setting but convenient. Close to desirable...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, Sleeps 9Quick View
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    • Grill
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    • Ocean Views
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    Pet friendly
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    Smoking allowed
    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...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 9
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    3 Bedrooms, Sleeps 8Quick View
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 8Quick View
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 5Quick View
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    • Central Heating
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    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...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    3 Bedrooms, Sleeps 6Quick View
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    5 Bedrooms, Sleeps 10Quick View
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, Sleeps 8Quick View
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    • Satellite TV
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 8Quick View
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    • Grill
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, Sleeps 9Quick View
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 9
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    About this property
    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...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 5Quick View
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    • Washer
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    Pet friendly
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    • Internet Access
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    • Outdoor Dining Area
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    2 Bedrooms, Sleeps 3Quick View
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    Pet friendly
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    Smoking allowed
    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,...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    5 Bedrooms, Sleeps 14Quick View
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    Pet friendly
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    Smoking allowed
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 14
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    5 Bedrooms, Sleeps 12Quick View
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    • Washer
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    • Balcony
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming 5 bedroom, 4 bath home located at Prospect Hill in Chilmark has a great layout and excellent location. Main level has generous kitchen, open living dining area, and master bedroom and bath, all light and bright with extensive decking and French doors to connect the interior to the...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    5 Bedrooms, Sleeps 10Quick View
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    Pet friendly
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    Smoking allowed
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    • Washer
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    Pet friendly
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    6 Bedrooms, Sleeps 14Quick View
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 3 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 6Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 4Quick View
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 Bedrooms, Sleeps 12Quick View
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    • Grill
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    • Patio
    • Hot Tub
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    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 flotilla of kayaks and paddle boards on the Pond, and private access to the Stonewall Beach, with beach chairs, toys and umbrellas...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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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...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 4Quick View
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    Amenities and Features include... Top Side Cottage, set in the Iconic Village of Menemsha and Overlooking all of Menemsha Harbor, 300 Yards to the Beach, 50 Yards to the Market, 200 yards to Village, Fish Markets and Eateries Additional amenities include: coffee maker, patio table and chairs,...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    About this property
    The Zaccheus Mayhew House (1713) has been described as “the largest and most stately of the early houses on the South Road.” It recently (2016-17) underwent a complete gut renovation. It is now a fully functional contemporary home inside a Colonial post and beam frame. While it is mostly new, it...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 1
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    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...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Smoking allowed
    About this property
    Stunning Waterfront with spectacular views across Stone Pond to Stonewall Beach. Relax on the expansive decks overlooking the water with ocean views beyond. This is an immaculate updated home with waterviews from just about every room and is tastefully furnished, features a new chef's kitchen, 3...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    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...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    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...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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......
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 8Quick View
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    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,...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    This spacious, comfortably furnished home is conveniently located between Chilmark and West Tisbury. The master bedroom and a bath are downstairs; three bedrooms and a bath are upstairs off the loft that overlooks the living and dining rooms. The living and dining rooms have a cathedral ceiling,...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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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...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Smoking allowed
    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...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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    • Internet Access
    • Satellite TV
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 6Quick View
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    • Satellite TV
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    What a location! Located in Menemsha with classic Vineyard fishing village views this cottage is the quintessential vacation home. You can walk to the beach to picnic, fish or watch beautiful sunsets and you can also walk to one of the Island's most popular seafood restaurants. It is light, airy...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    • Satellite TV
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    Amenities & Details
    • Satellite TV
    • DVD Player
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Chilmark, Martha's Vineyard 02535
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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