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Vacation Rentals in Chilmark, MA

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    $1,595
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    1 / 12
    2 Bedrooms / 1 Bathroom / Sleeps 3
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    $345
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    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    5 of 5 stars (2) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 4
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    1 / 30
    5 Bedrooms / 4 Bathrooms / Sleeps 12
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    About this property
    Come enjoy the secluded beauty of this award-winning, architect-designed home in Chimark on almost four acres of land. Relax on the two level deck or on the beach at Lucy Vincent, Squibnocket, or nearby Menemsha. The remarkable design makes great use of over 3500-square-foot space by joining the... View all property information
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    1 / 20
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    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 / 29
    5 Bedrooms / 5 Bathrooms / Sleeps 10
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    About this property
    Tucked away in the prestigious Quansoo area of Chilmark, this architect-designed compound sits peacefully on the shores of the Tisbury Great Pond. There are sophisticated touches inside and out, with a Main House, Guest House, and key access to Quansoo Beach. The Main House is centered around a... View all property information
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    1 / 45
    5 of 5 stars (6) Excellent
    5 Bedrooms / 4 Bathrooms / Sleeps 9
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    • Air Conditioning
    • Balcony
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    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
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    • ?
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    • 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 December 27, 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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    1 / 23
    6 Bedrooms / 4 Bathrooms / Sleeps 10
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    • Water Views
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    About this property
    Contemporary Home commands one of Martha's Vineyard's most spectacular views overlooking the Elizabeth Islands and Vineyard Sound. Breathtaking sunsets. Outdoor patios and deck and multiple living areas provide many options for family gatherings or quiet times. Amenities and Features include...... View all property information
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    1 / 24
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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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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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    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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    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    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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    1 / 28
    6 Bedrooms / 6 Bathrooms / Sleeps 12
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    About this property
    Vista Point combines a truly magical mix of a spectacular, waterfront location, with equaling stunning architectural design. Sitting high atop a north shore ridge in Chilmark, the views stretch west from the Aquinnah cliffs and lighthouse, north to the Elizabeth Islands, and east toward Lambert's... View all property information
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    1 / 31
    7 Bedrooms / 4 Bathrooms / Sleeps 9
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    About this property
    Serenely tucked away on the rolling hills and meadows of prestigious Seven Gates Farm, this Classic Chilmark home sits directly on the north shore with stunning water views of Vineyard Sound and the Elizabeth Islands, with its own curving coastline of Seven Gates beach. There is vintage charm... View all property information
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    $2,700
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • x
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    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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    4 Bedrooms / 3 Bathrooms / Sleeps 10
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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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    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    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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    $10,300
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    1 / 40
    5 Bedrooms / 5 Bathrooms / Sleeps 10
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    About this property
    Aptly named for its stunning perch in prestigious Squibnocket Farm on the shores of Squibnocket Pond, The Roost features panoramic water views that stretch from the far southwestern shoreline of Martha's Vineyard, across Chilmark's Squibnocket and Stonewall Beaches, and continue along the Island's... View all property information
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    1 / 22
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    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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    1 / 24
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • x
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    About this property
    This charming boathouse is tucked right at the edge of Stonewall Pond and has fabulous views of the pond and barrier beach. Swim and kayak by day and relish the starlight by night with the waves roaring on Stonewall beach. Perfect for a small family or a couple looking to get away. Additional... View all property information
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    1 / 25
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    About this property
    A quiet oasis tucked away on Blueberry Ridge, the Hillside Hideaway enjoys a tranquil country setting with rolling meadows, and thoughtfully designed outdoor landscaping with patios and outdoor living spaces set amid nicely manicured grounds and gardens. Inside, the house is designed to enjoy the... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    Hill House sits atop a bluff along the shores of Stonewall Pond with panoramic water views of the Pond and Stonewall Beach, as well as views over Quitsa Pond in the other direction. There is also access to Stonewall Beach, one of Chilmark's most prestigious private association beaches. Hill House... View all property information
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    1 / 36
    4 Bedrooms / 5 Bathrooms / Sleeps 8
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    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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    5 Bedrooms / 3 Bathrooms / Sleeps 10
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    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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    $1,950
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    1 / 15
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • x
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    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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    1 / 19
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    Quietly tucked away in a pastoral setting on Blueberry Ridge, Meadow House features a modern interpretation of a sleek barn. The home is designed to enjoy the views of the surrounding secluded meadows both inside and out. The main living space features an open design floorplan with Living and... View all property information
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    5 Bedrooms / 3 Bathrooms / Sleeps 9
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    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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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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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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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    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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    5 Bedrooms / 4 Bathrooms / Sleeps 12
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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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    1 / 19
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    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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    5 Bedrooms / 3 Bathrooms / Sleeps 10
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    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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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    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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    5 Bedrooms / 2 Bathrooms / Sleeps 9
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    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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    1 / 18
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Water Views
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    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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    6 Bedrooms / 2 Bathrooms / Sleeps 14
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    • Dishwasher
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    • Grill
    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    A large rambling old family home where memories are made. The extended family can all join in a vacation full of laughter and play. The grounds are full of places for hide-and-go-seek. Privately set on Middle Road in the woods yet bathed in sunlight. The house has a string of bedrooms for all the... View all property information
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    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
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    About this property
    Fabulous Chilmark home offers two levels of living sapce. On the first floor there is a fully equipped kitchen open to the dining room, a living room with fireplace, built-ins and sliders to a deck overlooking a meadow and the most incredible water views. There is a half bath, a master suite with... View all property information
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    6 Bedrooms / 2 Bathrooms / Sleeps 11
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    • Dishwasher
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    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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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    5 Bedrooms / 4 Bathrooms / Sleeps 10
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    • Dishwasher
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    • Grill
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    • Satellite TV
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    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
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    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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    $4,150
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    4 of 5 stars (1) Very good
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Inquiry
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    • Air Conditioning
    • Dishwasher
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    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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 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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    $7,500
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    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    • Air Conditioning
    • Dishwasher
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    • Grill
    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
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    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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    $12,500
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    5 Bedrooms / 5 Bathrooms / Sleeps 10
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
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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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    3 Bedrooms / 1 Bathroom / Sleeps 6
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    • Dishwasher
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    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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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    $3,450
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Pets allowed
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    • Suitable for children
    • x
    • x
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    • ?
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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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    1 / 31
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Dishwasher
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    • Elder access
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    About this property
    This idyllic Chilmark vacation home has breathtaking views over Stonewall Pond to the Atlantic shoreline to the south. Views to the west and north feature the ever-changing vistas and boating activity of Quitsa and Menemsha ponds. The house exudes casual elegance and warmth, and offers a myriad of... View all property information
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    $8,000
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    4 Bedrooms / 2 Bathrooms / Sleeps 2
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    • Dishwasher
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    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Dishwasher
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    • Grill
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    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Panoramic Views of South Shore from across the Allen Farm to Noman's Land and beyond. This carefully designed and decorated home sets you in beauty and comfort. The deck features a gazebo. The yard is carefully landscaped and tended with trees strategically planted to offer privacy between the main... View all property information
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    $5,000
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    5 Bedrooms / 2 Bathrooms / Sleeps 9
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    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Sweeping views of Squibnocket Pond, Dunes, the South Shore, Nomans Land, to sunsets over Aquinnah. A great family getaway with access to Chilmark's famed Lucy Vincent and Squibnocket Beaches as well as a private association beach in Aquinnah. Roomy and inviting, this house offers 5 five bedrooms... View all property information
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    $2,680
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    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Dishwasher
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    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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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