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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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    Quiet home with beach & dock access, peek-a-boo ocean views!1 / 30
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    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, fans - portable,...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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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    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...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick 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, outdoor furniture, lobster...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Surround yourself with mid-century style at this four-bedroom Chilmark getaway, a beautiful and iconic Martha's Vineyard home with a private pool and an oceanview deck just a short drive from the beach. Designed by the famous architect Eliot Noyes, this 1960s home was once featured in Life...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    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...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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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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    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...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    ATLANTIC OCEAN BREEZES, GLORIOUS VIEWS!1 / 22
    (1)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Reviewed June 16, 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
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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,...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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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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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick 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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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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
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Smoking allowed
    About this property
    Vacation in Chilmark near the pristine shores of the Tisbury Great Pond in this brand new, custom contemporary built with only the best materials. Four-bedroom main house with a detached guest suite. Open living / dining/ kitchen area with cathedral ceilings and exposed beams overlooking a...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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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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    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...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    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...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    CHILMARK - Deer Run-French Country Style Farmhouse w/ Hot Tub1 / 50
    (4)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Reviewed July 7, 2014
    Just spent a very relax vacation in this country style house that gived us a family home feel outside of our home. The house is surround by green trees with beautiful wood logs...
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    About this property
    This home is 1/2 mile from Chilmark Center If you are having trouble with FERRY RESERVATIONS contact me via email or phone and I'll work with you. This home is minutes to both Lucy Vincent Beach (with both nude and regular bathing sections) and Squibnocket Beach. It is just up the hill from...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    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......
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick 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
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    CLASSIC VINEYARD FISHING VILLAGE VIEWS FROM THIS QUINTESSENTIAL COTTAGE1 / 12
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick 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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    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
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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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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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    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
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    6 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    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
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Looking for a private peaceful location and beach rights to beautiful Lucy Vincent beach all the while enjoying a spacious updated vacation home, look no further, This lovely updated 3 bedroom 2.5 bath home located off of North road features a large open kitchen with center prep island , breakfast...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    6 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    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
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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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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    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...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Charming Chilmark 3 Bedroom 3 Bath Vacation Home1 / 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Pet friendly
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    Smoking allowed
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    Located in Chilmark on Martha's Vineyard, this 3 bedroom, 3 bathroom property is a perfect spring, summer or fall getaway. Cathedral ceilings create bright, airy spaces. Amenities include air conditioning, high speed internet, washer/dryer, gas fireplaces, TV in all rooms, outdoor shower, slate...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Waterfront
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    Pet friendly
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    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 1 Quick View
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    Smoking allowed
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    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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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick 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
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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: beach chairs, coffee maker, patio table and chairs, fans - portable, lobster pot,...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick 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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Unique combination of 1940's camp-style home and new (2007) two-story addition. Beautiful Ocean views from all floors, two decks, two living rooms and wonderful prevailing SW breezes. Five minute walk to Ocean Beach adjacent to Lucy Vincent Beach. Access to private Able's Hill Association beach and...
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Airey Two Bedroom Menemsha cottage1 / 8
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
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    View all property information
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    Chilmark, Martha's Vineyard 02535
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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