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Chilmark Holiday Rentals

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    Travellers to Chilmark are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    1 Review
    3 Bedrooms, Sleeps 6Quick View
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    3 Bedrooms, Sleeps 7Quick View
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    2 Bedrooms, Sleeps 4Quick View
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    4 Bedrooms, Sleeps 8Quick View
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    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...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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
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    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
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    3 Bedrooms, Sleeps 6Quick 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...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 3 Bedrooms, 3 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
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    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
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 8Quick View
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    About this property
    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...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 8Quick View
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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
    Holiday Rental House - 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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Satellite TV
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    About this property
    The Pond House, located on Stonewall beach in Chilmark, is a charming cottage is situated on the edge of the rolling lawns of the main house. The beauty and serenity experienced here are what the Vineyard is all about; Stonewall Pond to the west, the Atlantic to the southeast. The house has two...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, Sleeps 4Quick View
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    About this property
    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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 6Quick View
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    • Air Conditioning
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    • Private Garden
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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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    About this property
    Note: New for 2017, all new master bath, new larger dining table and chairs in the dining area and a new teak dining table on the screened porch Charming recently renovated summer cottage features large open living room with sliders leading on to a screened porch and private deck beyond. Porch is...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    • Grill
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    • Patio
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Historic 18th century New England home in a private landscaped setting on two and 1/2 acres with a waterview over Vineyard Sound and the Elizabeth Islands; a detached two-car garage, bunkhouse; tennis court and in-ground heated lap pool located on Menemsha Inn Road in the Town of Chilmark. The...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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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
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    • Waterfront
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    Pet friendly
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    Smoking allowed
    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Satellite TV
    • Waterfront
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    Pet friendly
    Kid friendly
    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    • Wi-Fi
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    • Private Outdoor Pool (Unheated)
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A perfect vacation house with miles of hiking trails and the best vineyard beach at your doorstep. Enjoy the "play" pool which is 4 feet deep and nice to relax in on a beautiful sunny vineyard day. Built with water therapy and children in mind; handicapped accessible. Total privacy, in one of the...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Review
    2 Bedrooms, Sleeps 6Quick View
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    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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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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...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, Sleeps 12Quick View
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    About this property
    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...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    5 Bedrooms, Sleeps 9Quick View
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    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...
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    Chilmark, Martha's Vineyard
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 9
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    3 Bedrooms, Sleeps 6Quick View
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    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 4Quick 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...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, Sleeps 3Quick View
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    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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    4 Bedrooms, Sleeps 8Quick View
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    C-H-A-R-M-I-N-G is the only word to describe this privately set little contemporary with a big heart, tucked right into the woods in Spring Point. Lovely view of the Sound over the tree tops from the full length inside comfort of screened-in porch. Convenient kitchen opens into living and dining...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Review
    4 Bedrooms, Sleeps 8Quick View
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    Excellent of 5 bubbles
    Reviewed 16 June 2014
    We stayed at this gorgeous home with a large family group in March. Fortunately for us, the weather was ideal. We had a lovely stay - everything at the house was wonderful and...
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    About this property
    A boutique hotel experience in an unrivaled setting at the end of a one mile single lane road. Enjoy the sunrise from the ocean, sunset over the adjoining 13 acre Sheriff's Meadow Foundation conservation preserve. This home has a wonderful view toward Squibnocket Beach, a mile away, and the...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 8Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    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,...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    About this property
    Beautiful, custom 4-bedroom house in an exclusive neighborhood with private association beach and tennis court. Spacious, comfortable living and dining room with cathedral ceilings, open to kitchen and upstairs loft with office. TV/sitting room nook off dining room. Expansive deck with stunning...
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    Chilmark, Martha's Vineyard 02539
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    2 Bedrooms, Sleeps 5Quick View
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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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    • Air Conditioning
    • Satellite TV
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    • Patio
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    • Air Conditioning
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    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    • Patio
    • Grill
    • Satellite TV
    • Hot Tub
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious, 10 room, architectual award-winning design home perched atop a hill w/panoramic view of Vineyard Sound and the Elizabeth Islands. The large deck has marvelous water views and the sunsets are spectacular! Its charming interior includes a Living Room with vaulted ceilings,fireplace and...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, Sleeps 10Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    • Satellite TV
    • Grill
    • Internet Access
    • Air Conditioning
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 1
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    • Internet Access
    • Satellite TV
    • DVD Player
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    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
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 8
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    6 Bedrooms, Sleeps 10Quick View
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    • DVD Player
    • Internet Access
    • Satellite TV
    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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......
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, Sleeps 8Quick View
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    • Satellite TV
    • Internet Access
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tastefully furnished and decorated with antiques and art. This upscale 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;...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 8Quick View
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    • Washer
    • Grill
    • Parking
    • Porch
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located at end of a dead-end dirt road on 1.5 acres with tall pines and oaks. Modified saltbox, owner designed & built in 1978 for potential active solar. First floor has a large country kitchen, living room, bathroom with antique claw foot bathtub & w/d, & 2 decks. Second floor has 2 bedrooms with...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    • Grill
    • Waterfront
    • DVD Player
    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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