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Vacation Rentals in Chilmark, MA

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    Travellers to Chilmark are booking July dates now. Secure your vacation rental today, and have the perfect trip.
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    $2,248
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    $14,988
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    $12,490
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    • Internet Access
    • DVD Player
    • Water Views
    • Grill
    • Air Conditioning
    • Satellite TV
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    • Deck
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    • Wheelchair access
    • Child-friendly
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    • Elder access
    • x
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    About this property
    Stunning Chilmark property with wonderful privacy, peace and tranquility. This Martha's Vineyard vacation rental offers access to two keyed private association beaches Squibnocket Association and Long Beach, distant peak of a view to the Atlantic Ocean with classic Chilmark living and access to... View all property information
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    Chilmark, Martha's Vineyard
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    $7,494
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    Amenities & Details
    • Dryer
    • Stereo System
    • Air Conditioning
    • Deck
    • Waterfront
    • Patio
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Watch the sun set from your private, romantic waterfront cottage with unparalleled views of Menemsha Pond, wetlands, ocean, Elizabeth Islands and Gay Head. Key to a private Gay Head Beach is included with rental. Additional amenities include: coffee maker, smoke free, ipod dock station, lobster... View all property information
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    Chilmark, Martha's Vineyard 02535
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    $26,229
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    Amenities & Details
    • Washer
    • Satellite TV
    • Dryer
    • Grill
    • DVD Player
    • Stereo System
    • Cooker
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Elder access
    • x
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    About this property
    Exclusive Chilmark retreat perfectly blends casual elegance with stunning waterviews and a private pool. Enjoy the ocean-facing deck which provides a front row seat with plenty of room for entertaining and outdoor dining. A truly magical mix of a spectacular waterfront location, situated atop a... View all property information
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    Chilmark, Martha's Vineyard 02535
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    $22,482
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    Amenities & Details
    • Grill
    • Dryer
    • Deck
    • Porch
    • Satellite TV
    • Stereo System
    • Fireplace
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Four bedroom contemporary Cape located directly on Chilmark Pond with desirable Hancock beach key. Tastefully decorated with all amenties including a cook s kitchen, pantry and laundry room adjacent to kitchen. Upstairs includes two bedrooms wtih bathrooms and sitting (tv) room with deck... View all property information
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    Chilmark, Martha's Vineyard 02535
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    $6,245
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    • Internet Access
    • Air Conditioning
    • Microwave
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    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
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    $24,980
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    Amenities & Details
    • Dishwasher
    • Grill
    • Deck
    • Air Conditioning
    • Fireplace
    • Internet Access
    • Satellite TV
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Stunning Chilmark rental home. This newly constructed contemporary home is situated high up from the water with fabulous views of the North Shore. There are numerous paths great for a hike or a run in the woods. Privacy, privacy, privacy. Great space in the main house with five bedrooms on the main... View all property information
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    Chilmark, Martha's Vineyard
    From
    $2,498
    / Week
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    Amenities & Details
    • Satellite TV
    • Grill
    • Stereo System
    • Internet Access
    • Microwave
    • Deck
    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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    Location Information
    Chilmark, Martha's Vineyard
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    $4,371
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    Amenities & Details
    • Internet Access
    • DVD Player
    • Ceiling Fans
    • Dishwasher
    • Microwave
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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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... View all property information
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    Chilmark, Martha's Vineyard
    From
    $9,992
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    5 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Dryer
    • Stereo System
    • Patio
    • Grill
    • Satellite TV
    • Internet Access
    • DVD Player
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Spacious up-island home situated high on hill of desirable Spring Point. Enjoy great sunsets and sweeping waterviews of the Atlantic on the outer decks and patio. Thoughtfully designed for privacy, two master bedrooms on either end of home, two living rooms one up and one down. Large kitchen,... View all property information
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    Chilmark, Martha's Vineyard 02535
    From
    $9,367
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • DVD Player
    • Shared Outdoor Pool...
    • Stereo System
    • Satellite TV
    • Air Conditioning
    • Dryer
    • Cooker
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Breathtaking south shore ocean views from this pastoral setting await you. This striking contemporary has great spaces for everyone. Lovely furnishings and decor. All this and Chilmark beaches too. Additional amenities include: coffee maker, smoke free, lobster pot, 1st floor bedroom, 1 king... View all property information
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    Chilmark, Martha's Vineyard 02535
    From
    $3,122
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    1 / 23
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Deck
    • Cooker
    • Porch
    • Stereo System
    • DVD Player
    • Satellite TV
    • Linens Provided
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Charming, remodeled in 2000, this is a seaside cottage overlooking Menemsha Harbor and beach. Bright and open interior with upscale details, the house is very comfortable. Master suite upstairs with deck and views of harbor, beach and sunsets. Backyard is private with outdoor deck and screened in... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    $3,435
    / Week
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    Amenities & Details
    • Satellite TV
    • Stereo System
    • DVD Player
    • Grill
    • Deck
    • Microwave
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Charming Chilmark cottage with panoramic South Shore waterviews. A five minute stroll to South surf beach. Private tennis courts shared with owners and other tenants. Access to Stonewall Pond for launching canoes and kayaks. Seaside cottage charm has been maintained throughout with tung and groove... View all property information
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    Chilmark, Martha's Vineyard
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    $4,122
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    5 Bedrooms / 4 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • 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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    Location Information
    Chilmark, Martha's Vineyard
    From
    $6,245
    / Week
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    1 / 24
    4 Bedrooms / 4 Bathrooms / Sleeps 9
    Overview Make Enquiry
    Amenities & Details
    • Fireplace
    • DVD Player
    • Stereo System
    • Internet Access
    • Porch
    • Grill
    • Air Conditioning
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Private up-island setting with sweeping distant water views. This four bedroom retreat is spacious, comfortable and well-appointed throughout with central a/c. Relax and enjoy summer days on the expansive upper deck with great views and fabulous sunsets. The upper level has an open living area -... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    $3,122
    / Week
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    Amenities & Details
    • Waterfront
    • Satellite TV
    • Grill
    • Deck
    • Internet Access
    • DVD Player
    • Washer
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Sunrise from the ocean, sunset over Stonewall Pond and view towards Squibnocket Beach. Old Vineyard look and feel, an elegant and comfortable beach house with landscaped gardens. Recently built 500 sq ft addition includes ground floor MBR suite offering full amenities. Services include: cleaning 3X... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    $16,237
    / Week
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    1 / 27
    5 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Waterfront
    • Satellite TV
    • Cooker
    • Grill
    • DVD Player
    • Dryer
    • Washer
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Architect designed, beautifully appointed home and guest house on five acres in Chilmark. Knoll wooded lot on Tisbury Great Pond, fronted on large native grass meadow. This bright and airy home offers complete privacy and access to Quansoo beach. Kayakers will delight in exploring the Great Pond... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    $4,122
    / Week
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    Amenities & Details
    • Internet Access
    • Stereo System
    • DVD Player
    • Waterfront
    • Grill
    • Porch
    • Deck
    • Satellite TV
    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
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    From
    $6,432
    / Week
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Grill
    • Porch
    • Deck
    • Internet Access
    • Ceiling Fans
    • Satellite TV
    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
    $3,560
    / Week
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    Amenities & Details
    • Deck
    • Air Conditioning
    • Dishwasher
    • Microwave
    • Patio
    • DVD Player
    • Satellite TV
    • Grill
    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
    $8,993
    / Week
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    Amenities & Details
    • Grill
    • Microwave
    • Internet Access
    • Air Conditioning
    • Patio
    • Satellite TV
    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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    Location Information
    Chilmark, Martha's Vineyard
    From
    $22,482
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    Amenities & Details
    • DVD Player
    • Washer
    • Porch
    • Internet Access
    • Dryer
    • Waterfront
    • Deck
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Beautiful converted barn located in exclusive Squibnocket Farm. Access to one of the Vineyards most pristine and private ocean beaches. This home has the original exposed beams and floor to ceiling windows offering spectacular views of the surrounding meadows, ocean, pond and gardens. Balconies and... View all property information
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    Chilmark, Martha's Vineyard 02535
    From
    $12,490
    / Week
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    Amenities & Details
    • Water Views
    • Waterfront
    • Stereo System
    • Satellite TV
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This sprawling farm house which neighbors the Blue Heron Farm in Chilmark is a found jewel with fabulous views. The property offers five beautifully decorated bedrooms each with their own vineyard charm. Four being in the main house and a bunk room perfect for kids over the garage. Enjoy your... View all property information
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    Chilmark, Martha's Vineyard
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    $4,247
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    Amenities & Details
    • Satellite TV
    • Internet Access
    • Dishwasher
    • Deck
    • Stereo System
    • Ceiling Fans
    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
    $4,996
    / Week
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    Amenities & Details
    • Internet Access
    • Microwave
    • Satellite TV
    • Fireplace
    • Dishwasher
    • Deck
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Tucked away in Chilmark full of peace, tranquility and privacy. This 3 bedroom 2 bathroom contemporary home offers plenty of space for indoor or outdoor living. As you dine on the back deck, there is a wonderful meadow to view and a hammock with your name on it. Indoor you will find all the... View all property information
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    Chilmark, Martha's Vineyard
    From
    $2,498
    / Week
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    Amenities & Details
    • Microwave
    • Deck
    • Stereo System
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    A very special Windy Gates offering. Four bedroom converted barn offers a large open first floor with kitchen, dining and living space. Great barn doors open to patio seating outside. Four bedrooms upstairs with one hall bath and a second bath at the bottom of the stairs. Enjoy this Martha's... View all property information
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    Chilmark, Martha's Vineyard
    From
    $4,371
    / Week
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    Amenities & Details
    • Dishwasher
    • Internet Access
    • Microwave
    • Stereo System
    • Water Views
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Sweeping views over Quitsa and Menemsha Ponds to the Elizabeth islands and Vineyard sound. Contemporary Martha's Vineyard vacation rental in Chilmark with open kitchen, dining and living area. Natural light from picture windows and sky lights. Shared Dock access. Great property for fun in the sun... View all property information
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    Chilmark, Martha's Vineyard
    From
    $3,404
    / Week
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    Amenities & Details
    • Deck
    • Water Views
    • Satellite TV
    • Grill
    • Dishwasher
    • Microwave
    • DVD Player
    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
    $10,616
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Deck
    • Satellite TV
    • Private Outdoor...
    • Microwave
    • Stereo System
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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,... View all property information
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    Chilmark, Martha's Vineyard
    From
    $7,869
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Dishwasher
    • Porch
    • Water Views
    • Patio
    • Satellite TV
    • Stereo System
    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
    $3,310
    / Week
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    Amenities & Details
    • 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
    $13,364
    / Week
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    Amenities & Details
    • Dishwasher
    • Grill
    • Patio
    • Water Views
    • Deck
    • Air Conditioning
    • Internet Access
    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
    $6,432
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    Amenities & Details
    • DVD Player
    • Deck
    • Porch
    • Water Views
    • Microwave
    • Dishwasher
    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
    $9,992
    / Week
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    Amenities & Details
    • Deck
    • Dishwasher
    • Fireplace
    • Internet Access
    • Microwave
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
    • x
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    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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    Location Information
    Chilmark, Martha's Vineyard
    From
    $1,499
    / Week
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    Amenities & Details
    • Internet Access
    • Fireplace
    • Water Views
    • Stereo System
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Delightful Cape GUEST HOUSE situated on the grounds of a hilltop Chilmark estate. (Estate's Main House is rented separately and may be occupied). Magnificent views over Menemsha Pond. Access to Hancock Beach with adjacent parking and Menemsha Pond within walking distance. First floor has an open... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    $34,972
    / Week
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    Amenities & Details
    • Deck
    • DVD Player
    • Stereo System
    • Grill
    • Fireplace
    • Waterfront
    • Satellite TV
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    About this property
    Chilmark retreat at its finest. This tranquil and extremely private setting is on the south side side of Martha's Vineyard within close proximity of the stunning Lucy Vincent Beach. This sprawling well designed six bedroom fully air conditioned ranch style home gives you plenty of indoor lounging... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    $24,980
    / Week
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    Amenities & Details
    • Dishwasher
    • Grill
    • Satellite TV
    • Shared Outdoor Pool...
    • Deck
    • Microwave
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • ?
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    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Spectacular contemporary Martha's Vineyard vacation rental offering 5,000 square feet of casually elegant living space. Overlooking Chilmark pond and Lucy Vincent Beach with professionally landscaped grounds. Enjoy lounging on the deck with an in-ground negative edge swimming pool. Additional... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    $2,498
    / Week
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    Amenities & Details
    • Air Conditioning
    • Stereo System
    • Dishwasher
    • Satellite TV
    • Grill
    • Microwave
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Lovely Chilmark Cottage for rent. Situated with privacy in a wooded area not too far from beaches and Alley's General Store. Enjoy peaceful mornings and evenings on the private deck while heading to the beautiful South Shore on Lucy Vincent Beach during the sunny Vineyard days. Walk into this... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    $3,347
    / Week
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    Amenities & Details
    • Microwave
    • Stereo System
    • Satellite TV
    • Grill
    • Internet Access
    • DVD Player
    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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    Location Information
    Chilmark, Martha's Vineyard
    From
    $7,744
    / Week
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    1 / 9
    Amenities & Details
    • 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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    Location Information
    Chilmark, Martha's Vineyard
    From
    $2,436
    / Week
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    Amenities & Details
    • Grill
    • Satellite TV
    • Ceiling Fans
    • Air Conditioning
    • Dishwasher
    • Deck
    • Stereo System
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Amenities and Features include... North Slope Hilltop House. Private yard, Screeen Porch and Patio, All new AC Throughout, 8 minute drive to Lucy Vincent Beach or Menemsha Village Additional amenities include: coffee maker, patio table and chairs, fans - portable, lobster pot, washer / dryer, cd... View all property information
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    Chilmark, Martha's Vineyard
    From
    $10,616
    / Week
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    1 / 23
    6 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Water Views
    • Grill
    • Dishwasher
    • Patio
    • Microwave
    • Satellite TV
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Smoking allowed
    • Elder access
    • x
    • ?
    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...... View all property information
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    Location Information
    Chilmark, Martha's Vineyard
    From
    $3,122
    / Week
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    1 / 14
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Cooker
    • Washer
    • Satellite TV
    • Stereo System
    • Linens Provided
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    About this property
    This charming newly remodeled three bedroom, two bath Cape has a spacious master bedroom suite, cozy sun room and updated kitchen. Spend your Chilmark vacation here and enjoy rights to desirable Lucy Vincent and Squibnocket beach. A memorable up-island retreat awaits you! Additional amenities... View all property information
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    Location Information
    Chilmark, Martha's Vineyard 02535
    From
    $3,716
    / Week
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    1 / 16
    Amenities & Details
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Dishwasher
    • Stereo System
    • 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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    Location Information
    Chilmark, Martha's Vineyard
    From
    $4,996
    / Week
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    Amenities & Details
    • Waterfront
    • Ceiling Fans
    • Air Conditioning
    • Grill
    • Water Views
    • Microwave
    • Deck
    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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    Location Information
    Chilmark, Martha's Vineyard
    From
    $5,558
    / Week
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    1 / 18
    Amenities & Details
    • Air Conditioning
    • Water Views
    • DVD Player
    • Internet Access
    • Microwave
    • Dishwasher
    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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    Location Information
    Chilmark, Martha's Vineyard
    From
    $5,620
    / Week
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    1 / 18
    Amenities & Details
    • Water Views
    • Air Conditioning
    • Waterfront
    • Grill
    • DVD Player
    • Microwave
    • Satellite TV
    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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    Location Information
    Chilmark, Martha's Vineyard
    From
    $3,966
    / Week
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    Amenities & Details
    • 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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    Location Information
    Chilmark, Martha's Vineyard