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Vacation rentals in Cuttyhunk, MA and nearby

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    All 128 Rentals in the Cuttyhunk Area
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    From
    $757
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    1 / 7
    Cuttyhunk
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    1 / 23
    Cuttyhunk
    8 Bedrooms / 8 Bathrooms / Sleeps 22
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    The following rentals are within 15 kilometres of Cuttyhunk, Massachusetts.

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    $435
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    1 / 10
    5 of 5 stars (1) Excellent
    Chilmark
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    traveller have booked this property
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    $404
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    1 / 26
    5 of 5 stars (2) Excellent
    Chilmark
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This small cottage on a hill, built in the 1950's, has been updated for comfort and style while maintaining the feel of the old-time Vineyard. One bedroom, one bathroom, a computer room, and a great room that includes kitchen, living, and dining area fit comfortably into 450 square feet. Many... View all property information
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    $498
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    1 / 14
    5 of 5 stars (6) Excellent
    Aquinnah
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Built in 2007, this ocean front home has a private trail through rolling sand dunes down to a white sand beach that stretches for miles. Right out front is Dog Fish Bar, a world class fishing location. Sand bars stretch for a mile right out front making for great adventuring at low tide. A great... View all property information
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    5 of 5 stars Reviewed 26 November 2014
    I didn't think the house and views could exceed the gorgeous pictures posted, but they do! First time to Martha's Vineyard, myself, my 2 sons and their girlfriends (from NY, NJ...
    5 of 5 stars Reviewed 5 October 2014
    Perfect place for people who want to be away from the crowds and enjoy privacy. The house is clean, tidy, beautifully furnished and even better than the photos. Very spacious...
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    $2,776
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    1 / 22
    Aquinnah
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
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    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Watch the boaters come and go, the sunset in the evening and feel the ocean breezes from this post & beam style 3 bedroom home. Open living spaces offer comfortable living that include living, dining and kitchen that open to a wide deck with Vineyard Sound views looking out toward the Elizabeth... View all property information
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    1 / 23
    Aquinnah
    2 Bedrooms / 2 Bathrooms / Sleeps 3
    travellers have booked this property
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    Amenities & Details
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This house is the perfect spot for enjoying the beauty and calm of Aquinnah. Light-filled, inviting and private, the house has multiple levels and sits on over an acre of wooded land with stone walls and a stream running through the property. Inside, the house offers wood floors throughout, a... View all property information
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    $1,136
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    1 / 30
    Chilmark
    5 Bedrooms / 4 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    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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    $3,028
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    1 / 24
    Chilmark
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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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    $4,732
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    1 / 20
    Chilmark
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    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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    $3,554
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    1 / 7
    Aquinnah
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Mountain Views
    • Ocean Views
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    About this property
    This 'up island' house is on a hill overlooking Menemsha Pond, on Martha's Vineyard, very near the famous clay cliffs. Watch the sunrise from the wall of windows in the living room. There are three bedrooms, an updated kitchen, dining area, washer and dryer. The house sits on nearly four acres.... View all property information
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    $2,013
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    1 / 12
    Chilmark
    2 Bedrooms / 1 Bathroom / Sleeps 3
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • 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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    $568
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    1 / 26
    Aquinnah
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Ocean Views
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Walk to Philbin Beach from this lovely, easy, breezy vacation home with secret garden, acres of privacy, birdsong and oceanbreezes and views will make your stay relaxing and restore your senses and refresh your body mind and soul. We offer an ECO Green house, providing only the best 100% Cotton... View all property information
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    $811
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    1 / 45
    5 of 5 stars (6) Excellent
    Chilmark
    5 Bedrooms / 4 Bathrooms / Sleeps 9
    Overview Reviews (6) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    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 / 15
    Aquinnah
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Lovely four bedroom, two and a half bath home located in Aquinnah.  This home has all the amenities you will need while on vacation.  Wonderful views of the ocean and the Gay Head Lighthouse.  The ground level porch has been partial enclosed, this provides a comfortable space for relaxing and... View all property information
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    $3,154
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    1 / 23
    5 of 5 stars (1) Excellent
    Chilmark
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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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    $5,236
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    1 / 10
    4 of 5 stars (1) Very good
    Chilmark
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • 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 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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    $4,290
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    1 / 13
    4 of 5 stars (1) Very good
    Aquinnah
    3 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Private beach with mooring!Hot fishing spot known as Dogfish bar!Beautiful renovated home.1 minute walk to the beach through our deeded sand dune!Views through out this home.It has everything! Granite kitchens and baths! Seating for at least 12. Open floor plan. Hardwood floors. 3 BR 2 Full... View all property information
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    4 of 5 stars Reviewed 22 July 2014
    Open and spacious home that had an amazing backyard for our kids to run around. Ocean views and French doors that made every morning and evening inviting. We loved our stay at...
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    $5,930
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    1 / 16
    Aquinnah
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
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    • Dishwasher
    • Grill
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Amenities and Features include... Light House Rd Contemporary Retreat with Spectacular Unobstructed Waterviews over the North Shore. Sunsets, Gorgeous Aquinnah Beaches Additional amenities include: coffee maker, fans - portable, lobster pot, washer / dryer, outside shower - enclosed, outdoor... View all property information
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    From
    $3,407
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    1 / 20
    Chilmark
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
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    • Dishwasher
    • Dryer
    • 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
    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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    From
    $3,785
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    1 / 24
    Chilmark
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
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    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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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    $5,300
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    1 / 30
    Menemsha
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Don't miss this rare opportunity to vacation in a beautifully renovated 275 year old antique New England Cape. Private beach front on Menemsha Pond is a short walk from the house. Built in the 1700's for Captain John Pease and his wife, Hannah, this 3 bedroom home is steeped in history and has been... View all property information
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    $8,833
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    1 / 34
    Aquinnah
    5 Bedrooms / 7 Bathrooms / Sleeps 10
    Overview Make Enquiry
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    • Dishwasher
    • Dryer
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    • Internet Access
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This architecturally distinctive contemporary sits quietly atop an Aquinnah ridge, looking out to the south shore with sunset water views. Designed with those views in mind, many of the rooms in the home have ocean views or Gay Head lighthouse views in a more northernly direction. The main floor... View all property information
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    $3,533
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    1 / 21
    Chilmark
    5 Bedrooms / 4 Bathrooms / Sleeps 12
    Overview Make Enquiry
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    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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 / 39
    Chilmark
    5 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    \'Wingate Roost\' This exquisite post and beam home sits on a high ridge in one of the most desirable areas on the Vineyard. The views are stunning in every direction, spanning over the entire length of Squibnocket Pond to the fabulous dunes of the barrier beach all the way to Noman's Land. To the... View all property information
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    $8,833
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    Aquinnah
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Enquiry
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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
    • ?
    • ?
    About this property
    Set atop a hill overlooking Menemsha, Quitsa, and Squibnocket Ponds and the Atlantic Ocean beyond, rests this stunning home. Expertly designed by the owners, sets this unique house apart. The soothing sound of a waterfall greets you as you approach the Koi-filled pond and the house. Take in the... View all property information
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    $10,725
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    1 / 23
    Chilmark
    6 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Make Enquiry
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    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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 / 15
    Chilmark
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
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    • 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
    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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    $2,461
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    1 / 15
    Chilmark
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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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    $2,524
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    1 / 22
    Chilmark
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
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    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • ?
    • ?
    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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    $3,382
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    1 / 18
    Chilmark
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
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    • Dishwasher
    • Grill
    • Internet Access
    • 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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    $5,047
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    1 / 22
    Chilmark
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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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    From
    $6,183
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    1 / 21
    Aquinnah
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Walk off the deck of this wonderful beach house right onto the dunes! Enjoy swimming, fishing, sailing, snorkeling, or just relaxing the day away. At the end of the day, watch the spectacular sunsets! When Dogfish bar surfaces, collect sand dollars. Comb the beach for shells and sea glass. Live in... View all property information
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    $6,498
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    Chilmark
    1 Bedroom / 2 Bathrooms / Sleeps 3
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    • Dishwasher
    • Grill
    • Satellite TV
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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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    1 / 18
    Aquinnah
    6 Bedrooms / 3 Bathrooms / Sleeps 11
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    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    'This beautifully decorated and appointed private residence has many comforts and conveniences and is one of the premier vacation rentals on Martha's Vineyard. Spectacular sunsets & ethereal views in a serene setting make this a most desirable location. It has features which others do not: CENTRAL... View all property information
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    $3,754
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    Chilmark
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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 barbeques. A... View all property information
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    $7,886
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    1 / 19
    Chilmark
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • 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
    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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    $5,331
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    1 / 26
    Chilmark
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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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    $3,344
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    Chilmark
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
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    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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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    1 / 37
    Aquinnah
    5 Bedrooms / 5 Bathrooms / Sleeps 8
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    Amenities & Details
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Set atop a hill overlooking Menemsha, Quitsa, and Squibnocket Ponds and the Atlantic Ocean beyond, rests this stunning home. A masterful combination of up-island elegance, fine craftsmanship, and expert design sets this house apart. The soothing sound of a waterfall greets you as you approach the... View all property information
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    $6,120
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    1 / 6
    Chilmark
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
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    • Dishwasher
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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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    $3,407
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    Chilmark
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
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    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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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    $6,940
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    Chilmark
    5 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Enquiry
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    • 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
    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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    $4,416
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    1 / 25
    Chilmark
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
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    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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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    1 / 31
    Chilmark
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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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    $6,057
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    1 / 21
    Chilmark
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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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    $5,236
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    1 / 15
    Aquinnah
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Coastal cottage nestled in the dunes on a private and gorgeous North Shore beach. This peaceful beach retreat is a world away and just perfect for those looking to kick back in a seaside cottage and relax in the warm summer sun. Just a short walk down your private path to private North Shore beach.... View all property information
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    $7,571
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    1 / 29
    Aquinnah
    5 Bedrooms / 6 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This beautiful new custom home is situated on a private road and 4 acres overlooking expansive Atlantic Oceans views. Professionally decorated, this home features 5 bedrooms (all en suite) and 1 1/2 additional baths. The great room design hosts three distinct seating areas - seating for TV viewing,... View all property information
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    $3,785
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    1 / 24
    Aquinnah
    5 Bedrooms / 3 Bathrooms / Sleeps 9
    Overview Make Enquiry
    Amenities & Details
    • 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
    Fabulous House, Fabulous Views. Attention to detail throughout. A dream gourmet kitchen. Ocean Views from all of the bedrooms. 180 degree views from Squibnocket to Aquinnah South Shores. Stunning sunsets from the west porch, sometimes referred to as the Martini deck! Brilliant sunrises from the... View all property information
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    1 / 24
    Chilmark
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
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    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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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