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Vacation Rentals in Chilmark, MA

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    Travelers to Chilmark are booking September dates now. Secure your vacation rental today, and have the perfect trip.
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    $345
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    1 / 10
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    $250
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    1 / 22
    5 Bedrooms / 2 Bathrooms / Sleeps 9
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    $900
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    5 Bedrooms / 4 Bathrooms / Sleeps 12
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    $3,750
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Smoking allowed
    • Elder access
    • ?
    • ?
    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... View all property information
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    Chilmark, Martha's Vineyard 02535
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    $1,595
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    1 / 12
    2 Bedrooms / 1 Bathroom / Sleeps 3
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    • Air Conditioning
    • Washer
    • Grill
    • Refrigerator
    • Stereo System
    • DVD Player
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Great location. Menemsha Village. 2 bedroom cottage. Sunny interior. 1 bath, plus outdoor shower. Storage barn, cable tv, High Speed internet, washer. Walk to beach, harbor, dock, stores, restaurants. Currently available August only. $1595 per week. 2 wk minimum. Maximum occupancy 2 adults,... View all property information
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    Chilmark, Martha's Vineyard 02535
    From
    $1,500
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    1 / 17
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    Amenities & Details
    • DVD Player
    • Stereo System
    • Internet Access
    • Satellite TV
    • Waterfront
    • Fireplace
    • Washer
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    What could be a more elegant, peaceful and romantic hideaway for a week than the Pond House? It sits at the conjunction of ocean and land, pond and meadow, with a view beyond dazzling outside and a warm fire in the fireplace inside. Gourmet kitchen. Antique and comfortable furniture. Quality... View all property information
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    Chilmark, Martha's Vineyard 02535
    From
    $4,150
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    1 / 10
    4 of 5 stars (1) Very good
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Internet Access
    • Stereo System
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Deck
    • Dishwasher
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Owner Transfer Ferry Tickets - Please Inquire Situated on a cul-de-sac overlooking a private meadow with spreading oaks ensures privacy. The screened porch, meadow bench, hammock and second floor deck off the master bedroom provide quiet spots to get away. Amenities and Features include...... View all property information
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    Chilmark, Martha's Vineyard
    4 of 5 stars Reviewed August 11, 2014
    Great vacation. Home was clean, property is private and quiet and as always, very comfortable. Convenient location for our family vacation needs. Lack of recycling at house...
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    $4,000
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    1 / 8
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Water Views
    • Satellite TV
    • Grill
    • Deck
    • DVD Player
    • Waterfront
    • Stereo System
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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, internet - ethernet... View all property information
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    Chilmark, Martha's Vineyard
    From
    $1,750
    / Week
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    1 / 8
    2 Bedrooms / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Fireplace
    • Satellite TV
    • Internet Access
    • Stereo System
    • Deck
    • Grill
    • Dishwasher
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    A perfect up-island retreat - this charming two bedroom cottage has all that you could possibly imagine, nicely updated and comfort throughout. Enjoy Chilmark's famous beaches by day, relax on the screened porch with a book before dinner -- this is the meaning of rest and relaxation! Additional... View all property information
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    Chilmark, Martha's Vineyard 02535
    From
    $4,450
    / Week
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    1 / 18
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Water Views
    • Grill
    • Satellite TV
    • DVD Player
    • Dishwasher
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
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    Chilmark, Martha's Vineyard
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    From
    $3,175
    / Week
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    1 / 24
    4 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Waterfront
    • Microwave
    • DVD Player
    • Water Views
    • Deck
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Casual immaculately clean in picturesque Menemsha, Chilmark waterfront. Beautiful views. A short stroll to the beach, fish market, boutiques, fishing, and shore dinners. Guest House - Main House on property nearby may be occupied by Tenants or Owner. Amenities and Features include...... View all property information
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    Chilmark, Martha's Vineyard
    From
    $6,150
    / Week
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    1 / 14
    4 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • DVD Player
    • Internet Access
    • Water Views
    • Satellite TV
    • Stereo System
    • Dishwasher
    • Deck
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Sweeping water view over Vineyard Sound to the Elizabeth Islands. Freshly renovated Cape-style, three bedrooms, with sofa beds in den and sunroom, sleeps 8-10 people. Short walk to lovely Menemsha Village, and less than two miles to Lucy Vincent's Beach. Large, landscaped treed lot of 2.3 acres on... View all property information
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    Chilmark, Martha's Vineyard
    From
    $5,150
    / Week
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    1 / 31
    5 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Deck
    • Water Views
    • Satellite TV
    • Porch
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    MVVR EXCLUSIVE: Spectacular 5 bedroom, 4.5 bath retreat. Lovely distant waterviews overlooking the South Shore. Hilltop setting with privacy and a five minute drive to Lucy Vincent Beach. This spacious custom home has been decorated by one of the island's premier professionals. A combination of... View all property information
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    Chilmark, Martha's Vineyard
    From
    $4,225
    / Week
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    1 / 26
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Dishwasher
    • DVD Player
    • Water Views
    • Internet Access
    • Deck
    • Satellite TV
    • Waterfront
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This quintessential Chilmark home has been impeccably maintained and continuously updated. The dining and living areas open to a wrap around deck. Enjoy spectacular water views and sunsets from just about every room in the house. Stroll to the beach and Menemsha village where you will find the fish... View all property information
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    Chilmark, Martha's Vineyard
    From
    $2,000
    / Week
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    1 / 17
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    Overview Make Inquiry
    Amenities & Details
    • Stereo System
    • Air Conditioning
    • Dryer
    • Internet Access
    • Satellite TV
    • DVD Player
    • Washer
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Charming cottage with water view just steps into Menemsha. Great outdoor deck, new kitchen - everything recently updated. Wonderful antiques for decoration and top quality furnishings throughout. Additional amenities include: coffee maker, smoke free, 6 dining capacity, pets considered, lobster... View all property information
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    Chilmark, Martha's Vineyard 02535
    From
    $1,950
    / Week
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    1 / 15
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Grill
    • Deck
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Satellite TV
    • Stereo System
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Amenities and Features include... North Slope Hilltop House. Private yard, Screeen Porch and Patio, All new AC Throughout, 8 minute drive to Lucy Vincent Beach or Menemsha Village Additional amenities include: coffee maker, patio table and chairs, fans - portable, lobster pot, washer / dryer, cd... View all property information
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    Chilmark, Martha's Vineyard
    From
    $4,500
    / Week
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    1 / 18
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Waterfront
    • Dishwasher
    • DVD Player
    • Water Views
    • Deck
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Amenities and Features include... Quansoo (with private beach key), Central Air, Waterview, Waterfront Additional amenities include: coffee maker, internet - ethernet cord required, pets considered, lobster pot, washer / dryer, cd player, porch - screened, outside shower - enclosed, private... View all property information
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    Chilmark, Martha's Vineyard
    From
    $3,800
    / Week
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    1 / 24
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • DVD Player
    • Grill
    • Internet Access
    • Satellite TV
    • Waterfront
    • Air Conditioning
    • Water Views
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Owner Transfer Ferry Tickets - Please Inquire Stunning Waterfront Views. Kayak or swim across the pond to Stonewall Beach or just relax on the expansive decks overlooking the water. This is an immaculate older home, very comfortably furnished with 3 bedrooms and 2 baths. High Speed Internet.... View all property information
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    Chilmark, Martha's Vineyard
    From
    $5,150
    / Week
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    1 / 14
    1 Bedroom / 2 Bathrooms / Sleeps 3
    Overview Make Inquiry
    Amenities & Details
    • Dishwasher
    • DVD Player
    • Satellite TV
    • Waterfront
    • Deck
    • Grill
    • Water Views
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    'The Little House' on the beach. Two minute stroll to South surf beach. Incredible views from sunrise to sunset. Private tennis courts shared with owners and other tenants. Access to Stonewall Pond for launching canoes and kayaks. This wonderful cottage is a one of a kind. A pet will be considered... View all property information
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    Chilmark, Martha's Vineyard
    From
    $4,000
    / Week
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    1 / 14
    5 Bedrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Microwave
    • Internet Access
    • Water Views
    • Deck
    • Satellite TV
    • Dishwasher
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Stunning Chilmark rental property with beautiful views to the south across Squibnocket Pond and the Atlantic and to the north across Menemsha Pond to the Elizabeth Islands. The house was built in the 1950s in a manner to maximize the enjoyment of the wonderful setting and views. It is surrounded by... View all property information
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    Chilmark, Martha's Vineyard
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    From
    $2,680
    / Week
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    1 / 18
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Satellite TV
    • Grill
    • Microwave
    • Deck
    • Stereo System
    • DVD Player
    • Internet Access
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
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    Chilmark, Martha's Vineyard
    From
    $4,000
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    1 / 23
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Dishwasher
    • Water Views
    • Deck
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Waterfront
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Steps from Menemsha Pond – look across the ever-changing surface of the water to Menemsha, the Creek, the Lobsterville dunes, Vineyard Sound and the Elizabeth Islands. Magnificent sunsets from the living room. This cathedral-ceiling Modernist masterpiece is constructed entirely of Western red... View all property information
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    Chilmark, Martha's Vineyard
    From
    $2,000
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    1 / 12
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Grill
    • DVD Player
    • Stereo System
    • Satellite TV
    • Deck
    • Microwave
    • Internet Access
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Charming recently renovated summer cottage features large open living room with sliders leading on to a screened porch and private deck beyond. Porch is fully furnished for dining and relaxing, providing aditional outdoor living space. The deck is private and surrounded by the yard area. The house... View all property information
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    Chilmark, Martha's Vineyard
    From
    $7,200
    / Week
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    1 / 24
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Patio
    • Porch
    • DVD Player
    • Dishwasher
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Outstanding private rental home nestled on 7.2 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 air... View all property information
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    Chilmark, Martha's Vineyard
    From
    $5,000
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    1 / 17
    3 Bedrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Deck
    • Dishwasher
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Microwave
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Stunning Chilmark property in Abel's Hill. Convenient location with great proximity to association beach and tennis, not far from Chilmark and West Tisbury town centers. Surrounded by open rolling hills with Japanese garden and fire pit, offering great privacy. Just steps to wonderful walking... View all property information
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    Chilmark, Martha's Vineyard
    From
    $3,500
    / Week
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    1 / 11
    5 Bedrooms / 3 Bathrooms / Sleeps 12
    Overview Make Inquiry
    Amenities & Details
    • Satellite TV
    • Grill
    • Deck
    • Internet Access
    • DVD Player
    • Ceiling Fans
    • Dishwasher
    • Microwave
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Spacious, well furnished and equipped, comfortable home in quiet neighborhood on 3 acres. Two master bedrooms, one on each floor; pool table. Within walking distance (about 1 mile) to small North Shore beach (Great Rock Bite). Three mile drive to Lucy Vincent Beach. Amenities and Features... View all property information
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    Chilmark, Martha's Vineyard
    From
    $3,300
    / Week
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    1 / 21
    5 Bedrooms / 4 Bathrooms / Sleeps 12
    Overview Make Inquiry
    Amenities & Details
    • Dishwasher
    • Satellite TV
    • Deck
    • Microwave
    • Ceiling Fans
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
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    Chilmark, Martha's Vineyard
    From
    $12,000
    / Week
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    1 / 32
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    Amenities & Details
    • Deck
    • Private Outdoor...
    • Internet Access
    • Grill
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    7 acre Luxury Chilmark Estate in an Idyllic setting of stone walls, perennial gardens and orchards. Private pool and hot tub surrounded by a large deck and bordered by tiered rose gardens. A regulation tennis court is set a short walk across the meadow. There is a beautiful natural pond on the... View all property information
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    Chilmark, Martha's Vineyard
    From
    $3,400
    / Week
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    1 / 25
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Grill
    • Stereo System
    • DVD Player
    • Deck
    • Microwave
    • Internet Access
    • Satellite TV
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Tastefully furnished and decorated with antiques and art. This Chilmark summer home is an original Yankee Barn located off South Road that has all the accouterments for summer entertaining. The post and beam structure features a beautiful cathedral living room brightened by southern light; has... View all property information
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    Chilmark, Martha's Vineyard
    From
    $2,000
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    1 / 23
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • DVD Player
    • Patio
    • TV
    • Stereo System
    • Washer
    • Dryer
    • Internet Access
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Luxurious beachfront living in Chilmark with sweeping water views of Stonewall Beach, Squibnocket Ridge, and Stonewall Pond. The Pond House sits directly on the intersection of Stonewall Beach and Pond, with water views throughout the house and across the large wraparound deck. Walls of windows and... View all property information
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    Chilmark, Martha's Vineyard
    From
    $1,050
    / Week
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    1 / 11
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Dishwasher
    • DVD Player
    • Stereo System
    • Internet Access
    • Deck
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Immaculate 4 bedroom in a private setting yet just a 10 minute drive to town or the most beautiful Lucy Vincent Beach. Features include large deck and wifi internet. The house has an open floor plan and an additional family/tv room for your comfort. Amenities and Features include... Large Deck,... View all property information
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    Chilmark, Martha's Vineyard
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    $2,700
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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Waterfront
    • Water Views
    • Stereo System
    • Porch
    • Satellite TV
    • Internet Access
    • Deck
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Owner Transfer Ferry Tickets - Please Inquire 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... View all property information
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    Chilmark, Martha's Vineyard
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    $2,975
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Stereo System
    • Satellite TV
    • Deck
    • Dishwasher
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Charming 4 bedroom, 3 bath traditional summer cottage. Enjoy this impeccably maintained summer home surrounded by a mature landscaped yard with lots of flowering shrubbery. A large deck offers privacy and a wonderful setting for those summer barbecues. A modern well equipped kitchen opens to the... View all property information
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    Chilmark, Martha's Vineyard
    From
    $3,300
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Stereo System
    • Grill
    • Waterfront
    • DVD Player
    • Water Views
    • Satellite TV
    • Internet Access
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Owner Transfer Ferry Tickets - Please Inquire 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.... View all property information
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    Chilmark, Martha's Vineyard
    From
    $3,000
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    5 Bedrooms / 3 Bathrooms / Sleeps 9
    Overview Make Inquiry
    Amenities & Details
    • Washer
    • Patio
    • DVD Player
    • Deck
    • Dryer
    • TV
    • Stereo System
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    The ultimate artist or family retreat tucked away amid the rolling hills and stonewalls of Squibnocket Pond in Chilmark. The panoramic water views look out across the Pond, the barrier beach and sand dunes of the Island's southwestern most point, and on out to No Man's Island and the Atlantic... View all property information
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    Chilmark, Martha's Vineyard
    From
    $2,650
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • DVD Player
    • Dishwasher
    • Ceiling Fans
    • Deck
    • Satellite TV
    • Internet Access
    • Grill
    • Microwave
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Lovely 3 bedroom 2 bath home. All new kitchen and baths. Completely renovated - lots of glass for a light filled interior. This lovely home in a private setting is surrounded by mature Holly trees, Laurel and attractive native shrubs. 1 mile to Alley's General Store. 10 minute drive to Lucy Vincent... View all property information
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    Chilmark, Martha's Vineyard
    From
    $2,850
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    5 Bedrooms / 2 Bathrooms / Sleeps 10
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    Amenities & Details
    • Internet Access
    • Private Outdoor...
    • Patio
    • Deck
    • Grill
    • Air Conditioning
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Beautiful newly remodeled and newly furnished 4 bedroom home with private pool. Landscaping bordering the house and pool will be enhanced and ready for summer 2015, work to begin in April. Ten minute drive from the house to Menemsha village or Lucy Vincent beach. The house features a cook's kitchen... View all property information
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    Chilmark, Martha's Vineyard
    From
    $1,250
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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    Amenities & Details
    • Deck
    • Microwave
    • Satellite TV
    • Internet Access
    • Grill
    • Water Views
    • DVD Player
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Amenities and Features include... Menemsha, Waterview, Walk to beach Additional amenities include: coffee maker, fans - portable, lobster pot, food processor, washer / dryer, cd player, outside shower - enclosed, vacuum, outdoor furniture, ironing board. View all property information
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    Chilmark, Martha's Vineyard
    From
    $6,300
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    4 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Water Views
    • Stereo System
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Patio
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This incredible home is furnished with one of a kind artisan wood and textile pieces, as well as Donghia soft seating and is filled with art, vintage stain glass, antiques, and one of kind artisan furniture. The ocean view is spectacular from the great room (living room, dining area and kitchen,... View all property information
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    Chilmark, Martha's Vineyard
    From
    $2,500
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    4 Bedrooms / 5 Bathrooms / Sleeps 8
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    Amenities & Details
    • Internet Access
    • Dryer
    • Stereo System
    • Deck
    • Washer
    • TV
    • DVD Player
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Featuring one of the most stunning water views and waterfront locations in Chilmark, The Beach House At Stonewall is just that. Stonewall Beach is directly at the property's edge. There is a private beach, and south-facing views of Stonewall Beach & Pond, Squibnocket Point, and on out to No Man's... View all property information
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    Chilmark, Martha's Vineyard
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    $3,500
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    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Stereo System
    • Internet Access
    • Water Views
    • DVD Player
    • Waterfront
    • Satellite TV
    • Grill
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Ocean Front Splendor in an elegant and comfortable beach house. Sunrise from the ocean, sunset over the adjoining 13-acre Sheriff's Meadow Foundation conservation preserve. Walk to the Stonewall Association private beach. Two master bedrooms, two twin-bed bedrooms. All four bedrooms have private... View all property information
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    Chilmark, Martha's Vineyard
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    $20,700
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    Studio / 3 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Satellite TV
    • Water Views
    • Patio
    • Stereo System
    • Private Outdoor...
    • Internet Access
    • Air Conditioning
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Expansive views of Chilmark Pond and the Atlantic Shoreline. Deeded access to pond, dock and private ocean beach (please inquire for more information). Newly completed 5400 square foot luxury home with ... multiple decks overlooks the masterfully landscaped grounds, stone walls, and ocean views... View all property information
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    Chilmark, Martha's Vineyard
    From
    $10,000
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    4 Bedrooms / 2 Bathrooms / Sleeps 9
    Overview Make Inquiry
    Amenities & Details
    • Stereo System
    • Dishwasher
    • Satellite TV
    • Water Views
    • DVD Player
    • Grill
    • Deck
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
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    Chilmark, Martha's Vineyard
    From
    $6,200
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    4 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • Microwave
    • Deck
    • Water Views
    • DVD Player
    • Satellite TV
    • Grill
    • Waterfront
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Black Smith Valley. Classic Cape overlooking acres of pastoral meadows and across Squibnocket Pond to open ocean. Immaculate home accented with country antiques and comfortable beds with linens provided. Walk to Squibnocket Beach or drive to Lucy Vincent Beach or make use of the private association... View all property information
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    Chilmark, Martha's Vineyard
    From
    $2,500
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    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    Amenities & Details
    • Washer
    • Internet Access
    • Deck
    • Dryer
    • TV
    • DVD Player
    • Stereo System
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Privately tucked away in the rolling hills of the historic Tea Lane area, surrounded by conservation land, the newly renovated Chilmark Retreat features a sleek modern style, with a sunny, open floor plan. There are sharp designer touches throughout, mixed with monochromatic shades of white and... View all property information
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    Chilmark, Martha's Vineyard
    From
    $12,900
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    5 Bedrooms / 5 Bathrooms / Sleeps 10
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    Amenities & Details
    • Air Conditioning
    • Water Views
    • Dishwasher
    • Satellite TV
    • Internet Access
    • Patio
    • Deck
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Dramatic ocean views, idyllic one of a kind location in gated community, private ocean beaches are but a few of the desirable features of this all new 5 bedroom, 5 bath contemporary home, set in one of the most Idyllic landscapes on Martha's Vineyard. Situated hilltop this gorgeous summer home... View all property information
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    Chilmark, Martha's Vineyard
    From
    $2,400
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Satellite TV
    • Deck
    • Water Views
    • Microwave
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Pristine modern summer cottage with distant views of Lucy Vincent Beach, privately nestled on historic Eddy Farm, hillside, off of South Rd. This light filled home with acres of privacy is the perfect retreat for those looking for a long term summer stay in Chilmark with Lucy Vincent Beach just a... View all property information
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    Chilmark, Martha's Vineyard
    From
    $5,350
    / Week
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Dishwasher
    • Water Views
    • DVD Player
    • Private Outdoor...
    • Deck
    • Internet Access
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Enjoy the in ground pool and spectacular ocean views from this casual, mostly glass hill top contemporary. Kick back and relax by the pool in an area of splendid nature. Amenities and Features include... Spectacular Waterviews, Pool, WiFi Additional amenities include: coffee maker, pets... View all property information
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    Chilmark, Martha's Vineyard
    From
    $2,725
    / Week
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    1 / 14
    5 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Stereo System
    • DVD Player
    • Satellite TV
    • Deck
    • Dishwasher
    • Internet Access
    • Water Views
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Qeen bedroom and a full bath. Outdoor spaces for your vacation... View all property information
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    Chilmark, Martha's Vineyard
    From
    $8,000
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    1 / 26
    4 Bedrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Deck
    • Internet Access
    • Satellite TV
    • Dishwasher
    • Fireplace
    • Water Views
    • Stereo System
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Spectacular waterviews! This Martha's Vineyard vacation rental is situated on 3+ acres overlooking the Elizabeth Islands and the Vineyard sound. On a clear day you can catch a lovely view of the Aquinnah lighthouse. The outdoor living space is truly where you want to be. Each area used for various... View all property information
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    Chilmark, Martha's Vineyard