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Chilmark Vacation Rentals

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    Travellers to Chilmark are booking August dates now. Secure your vacation rental today, and have the perfect trip.
    All 59 Rentals in Chilmark
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    6 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
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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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
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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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    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
    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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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Satellite TV
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    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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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
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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
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
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    Smoking allowed
    About this property
    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, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
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    Pet friendly
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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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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • Patio
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    Pet friendly
    Kid friendly
    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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    5 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Grill
    • Wi-Fi
    • Ocean Views
    • DVD Player
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    • Balcony
    • Washer
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    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
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 9
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    Pet friendly
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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, fans - portable, lobster pot, washer / dryer, cd player, landscaped,...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Satellite TV
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    Pet friendly
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    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
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Simply charming home that enjoys one of the most breathtaking views you will ever see. Perched high on a hill, the views of Menemsha Pond, Vineyard Sound, the Elizabeth Islands beyond and the nearby marshlands with their abundant bird life are simply mesmerizing.The newly-refreshed home has open...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
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    Pet friendly
    Kid friendly
    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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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    6 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
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    Pet friendly
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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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    • 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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    ATLANTIC OCEAN BREEZES, GLORIOUS VIEWS!1 / 22
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    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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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    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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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    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
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    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...
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    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    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, 3 Bathrooms, Sleeps 8 Quick View
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    Smoking allowed
    About this property
    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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    Pet friendly
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    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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    5 Bedrooms, 3 Bathrooms, Sleeps 1 Quick View
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    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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    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Washer
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    • Parking
    • Porch
    • Central Heating
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    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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Waterfront
    • DVD Player
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    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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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    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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    Studio, 3 Bathrooms, Sleeps 10 Quick View
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    • Satellite TV
    • Patio
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    • Private Outdoor Pool (Unheated)
    • Grill
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful views of Chilmark Pond and the Atlantic Shoreline. Deeded access to pond, dock at the pond and private ocean beach (please inquire for more information). This exquisite 5400 square foot luxury home features multiple decks which overlook the masterfully landscaped grounds bordered by stone...
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    Chilmark, Martha's Vineyard 02535
    Condo/Apartment - 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in a tranquil setting overlooking Chilmark Pond off of South Road this is a magical summer vacation spot. Additional amenities include: coffee maker, outdoor shower, lobster pot, food processor, cd player, wine glasses, washer & dryer, ironing board.
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    Location Information
    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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