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Vacation Rentals in Chilmark, MA

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    All 176 Rentals in Chilmark
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    Travellers to Chilmark are booking June dates now. Secure your vacation rental today, and have the perfect trip.
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    From
    $420
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    1 / 10
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    $389
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    1 / 26
    5 of 5 stars (2) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 4
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    $4,561
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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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    $1,940
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    Amenities & Details
    • Refrigerator
    • Ceiling Fans
    • Stereo System
    • Cooker
    • Washer
    • Grill
    • Satellite TV
    • Microwave
    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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    $3,466
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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
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    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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    $782
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    1 / 45
    5 of 5 stars (6) Excellent
    5 Bedrooms / 4 Bathrooms / Sleeps 9
    Overview Reviews (6) Make Enquiry
    Amenities & Details
    • Fireplace
    • Washer
    • Air Conditioning
    • Water Views
    • Dryer
    • Internet Access
    • Deck
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This comfortable contemporary home located up-island in Chilmark, includes a key to a private beach, Blackpoint, and is ideal for laid-back Vineyard living, or elegant entertaining with both ocean and hillside view. The open floor plan for the common areas bring the outdoors inside with spectacular... View all property information
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    1 / 23
    5 of 5 stars (1) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • TV
    • Microwave
    • Deck
    • DVD Player
    • Dryer
    • Dishwasher
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Smoking allowed
    • Elder access
    • ?
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    About this property
    Unique waterfront living in the heart of Chilmark. The Boathouse sits directly on the shores of Stonewall Pond, with sweeping water views of the Pond, Stonewall Beach and the Atlantic Ocean. You also have access to Stonewall Beach -- one of Chilmark's most prestigious private association beaches.... View all property information
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    5 of 5 stars Reviewed 27 December 2013
    we have stayed in this property 3 years running in both June and July. It's the most peaceful spot imaginable (no mobile phone signal) with unending wildlife activity ( we have...
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    $3,649
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    1 / 23
    Amenities & Details
    • Deck
    • Porch
    • DVD Player
    • Grill
    • Internet Access
    • Patio
    • TV
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Smoking allowed
    • Elder access
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    About this property
    Pine Ridge Farm sits peacefully tucked away on three acres of gently rolling meadows surrounded by stone walls. At the center of the compound is a classic Royal Barry Wills cape that has been smartly designed and finely appointed. An open Great Room with Living and Dining Areas has a two-story... View all property information
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    $5,048
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    1 / 10
    4 of 5 stars (1) Very good
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Deck
    • Dishwasher
    • Air Conditioning
    • Ceiling Fans
    • DVD Player
    • Satellite TV
    • Microwave
    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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    4 of 5 stars Reviewed 11 August 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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    $3,041
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    1 / 22
    5 of 5 stars (1) Excellent
    4 Bedrooms / 5 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Fireplace
    • Washer
    • Water Views
    • Dryer
    • Grill
    • Deck
    • Stereo System
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    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... View all property information
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    5 of 5 stars Reviewed 16 June 2014
    We stayed at this gorgeous home with a large family group in March. Fortunately for us, the weather was ideal. We had a lovely stay - everything at the house was wonderful and...
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    $2,433
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    1 / 22
    Amenities & Details
    • Washer
    • TV
    • Stereo System
    • Deck
    • Porch
    • Dishwasher
    • DVD Player
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Located on Flanders Lane, this house sits up the hill and looks toward Menemsha. It is private and protected by the trees. Walk to watch sunsets in Menemsha or dine in one of the places to eat there or take in a day at the beach. Additional amenities include: beach chairs, dock/boat-slip, coffee... View all property information
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    $11,555
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    1 / 16
    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Water Views
    • Deck
    • Washer
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • ?
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    About this property
    Beautiful, custom 4-bedroom house in an exclusive neighborhood with private association beach and tennis court. Spacious, comfortable living and dining room with cathedral ceilings, open to kitchen and upstairs loft with office. TV/sitting room nook off dining room. Expansive deck with stunning... View all property information
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    1 / 25
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Deck
    • Dishwasher
    • Linens Provided
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Smoking allowed
    • Elder access
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    About this property
    CHILMARK,Black Point Beach Heaven Sand Sun Surf and an immaculate house and guest quarters too................WOW This is not a fancy posh beach house. It is a wonderful relaxing, immaculate vacation destination for you and your family. You will find peace, ocean breezes, the sound of the surf,... View all property information
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    $2,919
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    Amenities & Details
    • Microwave
    • Water Views
    • Deck
    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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    $6,264
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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
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    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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    $3,041
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    Amenities & Details
    • Satellite TV
    • Washer
    • Grill
    • Stereo System
    • Dryer
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located on South Road near Able's Hill, this family oriented house comes with access to a private South Shore beach across Chilmark Pond. Have fun boating, kayaking or canoeing across the pond to the beach. A family room in the lower level provides space for the younger members of the family to... View all property information
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    $3,406
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    1 / 21
    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
    • ?
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    • Smoking allowed
    • Elder access
    • x
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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... View all property information
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    $3,284
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    1 / 20
    Amenities & Details
    • Porch
    • Washer
    • Dryer
    • Grill
    • Internet Access
    • Microwave
    • Stereo System
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This bright and cheerful, wooded retreat is truly tranquil, yet just a little over a mile from West Tisbury village, with its General Store (Alley's), Farmer's Market, Artisan's Festivals and Flea Market. This home has been recently updated by its new owners. They have chosen the loveliest colors... View all property information
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    $12,163
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    Amenities & Details
    • Microwave
    • Deck
    • Grill
    • Dishwasher
    • Internet Access
    • Patio
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    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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    $10,339
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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
    • ?
    • ?
    • 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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    $3,618
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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
    • ?
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Ferry Tickets Available - Please Inquire 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... View all property information
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    $2,372
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    1 / 15
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Grill
    • Satellite TV
    • Ceiling Fans
    • Air Conditioning
    • Dishwasher
    • Deck
    • Stereo System
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Amenities and Features include... A/C, WiFi Additional amenities include: coffee maker, patio table and chairs, fans - portable, lobster pot, washer / dryer, cd player, landscaped, porch - screened, outside shower - enclosed, vacuum, outdoor furniture, ironing board. View all property information
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    $3,649
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    Amenities & Details
    • Microwave
    • DVD Player
    • Grill
    • Washer
    • Satellite TV
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Newly renovated kitchen. Great yard and deck. Tucked into the woods off South Road. 1.3 miles from West Tisbury town center. Access to Lucy Vincent and Squibnocket Beaches. Convenient location in Chilmark. West Tisbury Farmer's Market & Artisan's Market are just down the road. Relax in the privacy... View all property information
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    $4,865
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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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    $15,204
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    Amenities & Details
    • Dryer
    • Patio
    • Deck
    • Washer
    • Stereo System
    • Satellite TV
    • Fireplace
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Newly constructed home has open concept living area with 270 degree water views, abundant natural sunlight, central AC, high end appliances, hardwood floors, rooftop deck with seating to view gorgeous island sunsets, access to several private beaches,and high speed internet wifi. Additional... View all property information
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    $695
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    1 / 11
    3 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • Dryer
    • Water Views
    • Internet Access
    • Washer
    • Deck
    • Waterfront
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Light and bright with floor to ceiling sliding glass doors in every room. The views over the wetland to the pond are phenomenal. A truly magical spot to watch the glow of the Menemsha Sunset. A short walk to a private sandy beach for swimming, kayaking, or sunbathing. Recent improvements... View all property information
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Dryer
    • Washer
    • Stereo System
    • DVD Player
    • Internet Access
    • Microwave
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
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    About this property
    Enjoy sweeping water views across Stonewall Pond and Beach, as well as access to the private ocean beach at prestigious Stonewall Beach. Lenom House is tucked away between Stonewall and Quitsa Ponds, with dramatic water views of both well known Chilmark Ponds, plus the south shore and Stonewall... View all property information
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    $3,649
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    Amenities & Details
    • Grill
    • Deck
    • Microwave
    • Dryer
    • Satellite TV
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Reverse Contemporary Five Bedroom home just minutes to Menemsha. There are open living spaces with living room , dining room and kitchen that open to deck with waterviews of the North Shore. Just a short drive to famous Lucy Vincent Beach, Chilmark Store, library and Community Center. Walk to a... View all property information
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    $3,041
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    Amenities & Details
    • Grill
    • Deck
    • Washer
    • Satellite TV
    • Stereo System
    • Dryer
    • Fireplace
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    This newly remodeled 3 bedroom 2 bath has a spacious master bedroom suite, cozy sun room and updated kitchen. It has a great yard with garden landscaping, a perfect spot for outdoor dining. 1.5 miles from Alley's store. 3.3 miles to Lucy Vincent Beach.The bathrooms are fully remodeled. An easy,... View all property information
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    Amenities & Details
    • Dishwasher
    • Washer
    • Satellite TV
    • Microwave
    • Dryer
    • Patio
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This house is set in a pastoral surrounding. It has beautifully tended grounds with a Peter Rabbit enclosed flower garden and rolling lawns. The well equipped gourmet kitchen overlooks the dining and living rooms. There is a four season porch off the living room and a sun bathed deck. The... View all property information
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    $6,690
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    Amenities & Details
    • Stereo System
    • DVD Player
    • Dishwasher
    • Deck
    • Washer
    • Grill
    • Microwave
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This colorful and spacious home has room for a large family or a smaller one with guests. On breezy days, lounge in the sun on the back deck protected from the wind. Take in the sunsets from the back deck, sunrises from the kitchen deck. The house comes with boogie boards and beach toys, beach... View all property information
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    $2,676
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    Amenities & Details
    • DVD Player
    • Microwave
    • Stereo System
    • Dishwasher
    • Grill
    • Satellite TV
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    This special summer retreat affords unforgettable views, a quiet and private setting, an awesome deck to sit and watch and let it all go. Newly renovated gourmet kitchen. The hgouse has views from every room. Watch the sailboat races on Menemsha Pond, the herons, the deer and the hawks on the... View all property information
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    $1,824
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    Amenities & Details
    • Grill
    • Deck
    • Water Views
    • Stereo System
    • Patio
    • Satellite TV
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Main House on the same property may be occupied by Owner or another Tenant. Peaceful private setting on one of the most beautiful areas on the South Shore. Amenities and Features include... Waterfront Guest House, Private Beach Additional amenities include: coffee maker, internet - ethernet... View all property information
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    $3,223
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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
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    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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    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Elder access
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    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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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Waterfront
    • Grill
    • Satellite TV
    • Internet Access
    • Water Views
    • Porch
    • Microwave
    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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    • Stereo System
    • Microwave
    • Waterfront
    • Dishwasher
    • DVD Player
    • Satellite TV
    • Grill
    • Water Views
    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 your private beach. New 500 square foot addition, added for summer 2008, includes ground floor Master Bedroom suite,... View all property information
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    • Dishwasher
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    • Internet Access
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    • 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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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Pet-friendly
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    • Child-friendly
    • x
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    • x
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    About this property
    Perched high above the surrounding terrain, this affordable Chilmark rental offers sweeping views of the ocean and upisland all the way to Aquinnah. See the sunsets from the deck. It is spacious with 4 bedrooms to accommodate family and friends. See Chilmark rental #CH224 for family reunions or... View all property information
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    Amenities & Details
    • Internet Access
    • Grill
    • Porch
    • Dishwasher
    • DVD Player
    • Deck
    • Microwave
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Sitting high atop a ridge in Chilmark, the distant ocean views from Hilltop House stretch as far as Woods Hole and the Elizabeth Islands to Menemsha. The three-acre hillside setting is both spectacular and private. The recently renovated house has two walls of glass sliding doors that frame the... View all property information
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    5 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Dishwasher
    • Stereo System
    • DVD Player
    • TV
    • Dryer
    • Grill
    • Internet Access
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Privately tucked away on 20 acres of rolling hills and meadows that run along the shoreline of Squibnocket Pond, this mission-style home enjoys stunning sunset and water views across the Pond, the sand dunes of the Island's most southwestern point, and on across the Atlantic Ocean out to No Man's... View all property information
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    Amenities & Details
    • Microwave
    • Stereo System
    • Deck
    • Satellite TV
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Sit on the porch of this fabulous four bedroom home and take in the panoramic water views. Enjoy watching the sheep grazing around the property which is part of a working farm. Access a gorgeous south shore private beach by canoe or kayak. The home is private, comfortable and convenient to the... View all property information
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    • Porch
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    • Fireplace
    • Dryer
    • Satellite TV
    • Stereo System
    • Patio
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located in Menemsha down a dirt road to privacy and serenity, this house is constructed carefully and artfully. The space is light filled with cathedral ceilings in the living area grounded by a hand built fireplace. All decorations and objects have been carefully picked to accent the space with... View all property information
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    $5,139
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    • Water Views
    • Waterfront
    • Grill
    • Satellite TV
    • Microwave
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    • 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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    Amenities & Details
    • Satellite TV
    • Internet Access
    • Stereo System
    • Grill
    • Deck
    • Air Conditioning
    • DVD Player
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This spacious ten room, architectural award winning design home is perched high on a hill with panoramic views of the Vineyard Sound and the Elizabeth Islands. There are five bedrooms, four and one half baths, a large deck for entertaining and watching the breathtaking sunsets, and three outdoor... View all property information
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    Amenities & Details
    • Deck
    • Waterfront
    • Grill
    • Stereo System
    • DVD Player
    • Fireplace
    • Internet Access
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Contemporary, private, exquisite home set right on Tisbury Great Pond. Drive to Quansoo or kayak right from the house. Large, gorgeous gourmet kitchen, spacious living room with stylish fire place, large screened porch, water views through the trees all contribute to the heightened appeal of this... View all property information
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    • Washer
    • Stereo System
    • Dryer
    • Porch
    • Fireplace
    • Satellite TV
    • DVD Player
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This quintessential beach house offers proximity to Menemsha while being removed from traffic and the hustle and bustle. It comes with an updated and well equipped kitchen for dining delights with the fresh fish just around the corner. A screen porch looking out over the view. The perfect seat for... View all property information
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    Amenities & Details
    • Grill
    • Patio
    • DVD Player
    • Stereo System
    • Dishwasher
    • Washer
    • Microwave
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    This historic farmhouse is quietly tucked away above Menemsha Pond with sweeping sunset and water views of The Pond and Menemsha Harbor. The tranquil setting is classic Chilmark with rolling hills and stonewalls, plus a private association beach just a short stroll away on Menemsha Pond.... View all property information
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    $7,298
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    • Dishwasher
    • Internet Access
    • Fireplace
    • Washer
    • DVD Player
    • Grill
    • Deck
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Style, warmth, and comfort define this delightful farm house in Menemsha with a water view to the Vineyard Sound. The property is spacious and private. There is a tennis court shared by the occupants of the neighboring barn. The house comes with a key to a beach in Aquinnah on Moshup trail and a... View all property information
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