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Vacation Rentals in Chilmark, MA

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All 107 Rentals in Chilmark
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From
$320
Per Night
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1 / 26
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1 Bedroom, 1 Bathroom, Sleeps 4
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From
$1,595
Per Week
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1 / 12
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2 Bedrooms, 1 Bathroom, Sleeps 3
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From
$345
Per Night
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1 / 10
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3 Bedrooms, 3 Bathrooms, Sleeps 6
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$900
Per Night
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1 / 30
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5 Bedrooms, 4 Bathrooms, Sleeps 12
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Amenities & Details
  • Stove
  • Refrigerator
  • Washer
  • Parking
  • Dishwasher
  • Grill
  • Microwave
  • Fireplace
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • 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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From
$3,750
Per Night
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1 / 20
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • # Of Bathrooms
  • Number Of Bedrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • 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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From
$5,500
Per Week
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1 / 23
3 Bedrooms, 3 Bathrooms, Sleeps 6
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Amenities & Details
  • Microwave
  • # Of Bathrooms
  • Internet Access
  • Patio
  • DVD Player
  • TV
  • Dryer
  • Stereo System
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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From
$643
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1 / 45
5 Bedrooms, 4 Bathrooms, Sleeps 9
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Amenities & Details
  • Refrigerator
  • Stove
  • DVD Player
  • Dishwasher
  • Washer
  • TV
  • Parking
  • Patio
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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From
$2,000
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1 / 22
4 Bedrooms, 5 Bathrooms, Sleeps 8
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Amenities & Details
  • DVD Player
  • TV
  • Microwave
  • Dryer
  • VCR
  • Grill
  • Fax
  • Stereo System
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 June 16, 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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From
$15,500
Per Week
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1 / 13
5 Bedrooms, 4 Bathrooms, Sleeps 8
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Amenities & Details
  • Dryer
  • Washer
  • Fireplace
  • Deck
  • VCR
  • Dishwasher
  • Grill
  • Stereo System
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Located in a tranquil setting overlooking Chilmark Pond off of South Road this is a magical summer vacation spot. Additional amenities include: coffee maker, lobster pot, food processor, cd player, wine glasses, crib, cassette, pillows, outside shower, blankets, ironing board. View all property information
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From
$4,500
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1 / 18
4 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Dryer
  • Washer
  • Deck
  • DVD Player
  • TV
  • Fireplace
  • Grill
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
A fascinating, lovely classic Eliot Noyes (architect) contemporary in a private setting with spectacular views off the water looking toward Lucy Vincent beach and East towards West Tisbury. There is a great room (with dining, and living room and kitchen) with decks on either side (4-10 feet off the... View all property information
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From
$2,000
Per Week
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1 / 8
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Internet Access
  • Microwave
  • TV
  • Washer
  • Deck
  • Grill
  • Dryer
  • Porch
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
C-H-A-R-M-I-N-G is the only word to describe this privately set little contemporary with a big heart, tucked right into the woods in Spring Point. Lovely view of the Sound over the tree tops from the full length deck...dine inside comfort of screened-in porch. Convenient kitchen opens into living... View all property information
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From
$4,500
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1 / 8
4 Bedrooms, 4 Bathrooms, Sleeps 8
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Amenities & Details
  • Washer
  • Patio
  • Stereo System
  • VCR
  • TV
  • Dishwasher
  • DVD Player
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Unique combination of 1940's camp-style home and new (2007) two-story addition. Beautiful Ocean views from all floors, two decks, two living rooms and wonderful prevailing SW breezes. Five minute walk to Ocean Beach adjacent to Lucy Vincent Beach. Access to private Able's Hill Association beach and... View all property information
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From
$14,250
Per Week
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1 / 22
4 Bedrooms, 4 Bathrooms, Sleeps 8
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Amenities & Details
  • VCR
  • Fax
  • Hot Tub
  • Grill
  • TV
  • Washer
  • Stereo System
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
A complete complex in a beautiful, peaceful setting: main house and barn with built-in pool, hottub, private tennis court and pond. One can walk to a lovely North Shore beach. This complex is surrounded by roses and perennials. Also, beach stickers for Lucy Vincent and Squibnocket are provided.... View all property information
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From
$6,000
Per Week
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1 / 22
6 Bedrooms, 4 Bathrooms, Sleeps 12
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Amenities & Details
  • Fireplace
  • Deck
  • Dryer
  • Stereo System
  • TV
  • Washer
  • Grill
  • Water Views
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Historic 18th century New England home in a private landscaped setting on two and 1/2 acres with a waterview over Vineyard Sound and the Elizabeth Islands; a detached two-car garage, bunkhouse and tennis court located on Menemsha Inn Road in the Town of Chilmark. The dwelling is a charming and... View all property information
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1 / 24
1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • TV
  • Number Of Bedrooms
  • Dishwasher
  • # Of Bathrooms
  • Grill
  • Stereo System
  • Guest Count
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
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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From
$14,000
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1 / 16
5 Bedrooms, 6 Bathrooms, Sleeps 10
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Amenities & Details
  • Porch
  • DVD Player
  • Grill
  • Microwave
  • Stereo System
  • Fireplace
  • Dryer
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Vacation in Chilmark near the pristine shores of the Tisbury Great Pond in this brand new, custom contemporary built with only the best materials. Four-bedroom main house with a detached guest suite. Open living / dining/ kitchen area with cathedral ceilings and exposed beams overlooking a... View all property information
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From
$9,500
Per Week
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1 / 16
4 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Stereo System
  • Dryer
  • Deck
  • Fireplace
  • TV
  • DVD Player
  • Microwave
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • ?
  • ?
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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From
$7,500
Per Week
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1 / 22
6 Bedrooms, 6 Bathrooms, Sleeps 10
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Amenities & Details
  • DVD Player
  • Patio
  • VCR
  • Grill
  • Dryer
  • Fireplace
  • Hot Tub
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Spacious, 10 room, architectual award-winning design home perched atop a hill w/panoramic view of Vineyard Sound and the Elizabeth Islands. The large deck has marvelous water views and the sunsets are spectacular! Its charming interior includes a Living Room with vaulted ceilings,fireplace and... View all property information
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From
$1,050
Per Week
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1 / 13
4 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Stereo System
  • Microwave
  • DVD Player
  • Air Conditioning
  • Washer
  • Dishwasher
  • Grill
  • VCR
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
This spacious and comfortably furnished contemporary Cape is conveniently located between Chilmark and West Tisbury. The master bedroom and bath are downstairs; three bedrooms and a bath are upstairs off the loft that overlooks the living and dining rooms. The living and dining rooms have a... View all property information
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From
$2,000
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1 / 22
4 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Washer
  • Dryer
  • Porch
  • Dishwasher
  • TV
  • DVD Player
  • Grill
  • Stereo System
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
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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From
$1,000
Per Week
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1 / 11
2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • TV
  • VCR
  • Stereo System
  • Fireplace
  • Microwave
  • Dishwasher
  • Washer
  • Fax
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
The Pond House, located on Stonewall beach in Chilmark, is a charming cottage is situated on the edge of the rolling lawns of the main house. The beauty and serenity experienced here are what the Vineyard is all about; Stonewall Pond to the west, the Atlantic to the southeast. The house has two... View all property information
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From
$3,400
Per Week
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1 / 21
4 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Grill
  • Fax
  • DVD Player
  • Dryer
  • Dishwasher
  • Deck
  • Washer
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Tastefully furnished and decorated with antiques and art. This upscale Chilmark summer home is an original Yankee Barn located off South Road that has all the accoutrements for summer entertaining. The post and beam structure features a beautiful cathedral living room brightened by southern light;... View all property information
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From
$4,800
Per Week
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1 / 16
3 Bedrooms, 3 Bathrooms, Sleeps 6
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Amenities & Details
  • Microwave
  • Dryer
  • Patio
  • Fireplace
  • DVD Player
  • Stereo System
  • Washer
  • VCR
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Beautifully restored, maintained, and furnished, this 1740 Island farmhouse is situated on 80 private acres of glorious Chilmark hills overlooking Menemsha Pond and includes a small private association beach on Menemsha Pond to wend your way down to. A little bit of heaven on earth! Additional... View all property information
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From
$8,000
Per Week
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1 / 24
4 Bedrooms, 2 Bathrooms, Sleeps 2
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Amenities & Details
  • Stereo System
  • TV
  • Washer
  • Deck
  • Fireplace
  • Dishwasher
  • Patio
  • Microwave
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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From
$4,150
Per Week
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1 / 14
4 Bedrooms, 2 Bathrooms, Sleeps 10
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Amenities & Details
  • Deck
  • Water Views
  • TV
  • Internet Access
  • Microwave
  • Satellite TV
  • Grill
  • Stereo System
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Sweeping water view over Vineyard Sound to the Elizabeth Islands. Freshly renovated Cape-style, three bedrooms, with sofa beds in den and sunroom, sleeps 8-10 people. Short walk to lovely Menemsha Village, and less than two miles to Lucy Vincent's Beach. Large, landscaped treed lot of 2.3 acres on... View all property information
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From
$2,500
Per Week
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1 / 15
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Dishwasher
  • Guest Count
  • Microwave
  • Dryer
  • Satellite TV
  • Washer
  • TV
  • Stereo System
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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From
$2,700
Per Week
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1 / 20
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • DVD Player
  • Dishwasher
  • Microwave
  • Deck
  • Washer
  • Dryer
  • Stereo System
  • TV
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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From
$6,250
Per Week
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1 / 19
4 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Washer
  • Internet Access
  • TV
  • Stereo System
  • Number Of Bedrooms
  • Satellite TV
  • Deck
  • Microwave
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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From
$3,000
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1 / 18
5 Bedrooms, 2 Bathrooms, Sleeps 9
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Amenities & Details
  • Washer
  • DVD Player
  • Microwave
  • Internet Access
  • TV
  • Satellite TV
  • Grill
  • Dryer
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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From
$3,000
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1 / 21
5 Bedrooms, 3 Bathrooms, Sleeps 10
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Amenities & Details
  • Washer
  • Dishwasher
  • Dryer
  • Deck
  • Grill
  • DVD Player
  • Microwave
  • Patio
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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From
$3,325
Per Week
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1 / 17
6 Bedrooms, 2 Bathrooms, Sleeps 14
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Amenities & Details
  • Deck
  • Internet Access
  • Satellite TV
  • Grill
  • Microwave
  • Dryer
  • Dishwasher
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
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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From
$3,450
Per Week
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1 / 15
4 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Number Of Bedrooms
  • DVD Player
  • Guest Count
  • TV
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
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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From
$5,500
Per Week
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1 / 18
5 Bedrooms, 3 Bathrooms, Sleeps 10
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Amenities & Details
  • TV
  • DVD Player
  • Satellite TV
  • Washer
  • Internet Access
  • Dishwasher
  • Microwave
  • Grill
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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From
$2,500
Per Week
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1 / 12
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Deck
  • Stereo System
  • DVD Player
  • Dryer
  • Fireplace
  • Washer
  • Microwave
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
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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From
$2,500
Per Week
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1 / 21
4 Bedrooms, 4 Bathrooms, Sleeps 8
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Amenities & Details
  • Washer
  • Internet Access
  • Grill
  • Dishwasher
  • Dryer
  • Porch
  • TV
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Privately tucked away in the rolling hills of the historic Tea Lane area, surrounded by conservation land, the newly renovated Chilmark Retreat features a sleek modern style, with a sunny, open floor plan. There are sharp designer touches throughout, mixed with monochromatic shades of white and... View all property information
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From
$4,800
Per Week
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1 / 21
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Patio
  • Grill
  • Dishwasher
  • Dryer
  • DVD Player
  • TV
  • Stereo System
  • Microwave
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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$4,000
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1 / 20
3 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Deck
  • TV
  • Microwave
  • Stereo System
  • Dishwasher
  • Dryer
  • DVD Player
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
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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From
$2,500
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1 / 36
4 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Stereo System
  • Porch
  • TV
  • Washer
  • Grill
  • Dryer
  • Deck
  • Dishwasher
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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From
$3,000
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1 / 13
3 Bedrooms, 1 Bathroom, Sleeps 6
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Amenities & Details
  • DVD Player
  • Satellite TV
  • Internet Access
  • Dryer
  • Microwave
  • Number Of Bedrooms
  • Deck
  • Grill
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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From
$4,000
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1 / 22
4 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Grill
  • Microwave
  • Dryer
  • TV
  • Stereo System
  • Deck
  • Porch
  • DVD Player
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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$11,000
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1 / 15
5 Bedrooms, 4 Bathrooms, Sleeps 10
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Amenities & Details
  • Dryer
  • Patio
  • DVD Player
  • Dishwasher
  • Microwave
  • Deck
  • Fireplace
  • Grill
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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From
$7,500
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1 / 17
4 Bedrooms, 4 Bathrooms, Sleeps 10
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Amenities & Details
  • Washer
  • Stereo System
  • Patio
  • DVD Player
  • Microwave
  • Fireplace
  • Deck
  • Dishwasher
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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From
$12,500
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1 / 16
5 Bedrooms, 5 Bathrooms, Sleeps 10
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Amenities & Details
  • Microwave
  • Grill
  • Stereo System
  • Patio
  • Dryer
  • Dishwasher
  • Garage
  • Fireplace
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
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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From
$7,000
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1 / 18
6 Bedrooms, 4 Bathrooms, Sleeps 10
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Amenities & Details
  • Dryer
  • Garage
  • Fireplace
  • Stereo System
  • DVD Player
  • Patio
  • Microwave
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This gracious Vineyard elongated Cape overlooks the Keith Farm and the Atlantic Ocean beyond. The gourmet kitchen has just been beautifully renovated and is a dream. The living areas are all decorated with charm and all have views. The separate main house, with four bedrooms, and guest house, with... View all property information
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From
$1,950
Per Week
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1 / 15
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • VCR
  • Deck
  • Microwave
  • Stereo System
  • DVD Player
  • Air Conditioning
  • TV
  • Ceiling Fans
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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From
$3,200
Per Week
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1 / 17
3 Bedrooms, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Fireplace
  • Grill
  • Toaster
  • Washer
  • Dryer
  • Microwave
  • Internet Access
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Rustic colorful camp with a gorgeous water view right on Chilmark Pond. Sleeps six. Simple kitchen with all necessities. Wow your guests with gourmet meals from this quaint kitchen. Comfortable living-dining overlooking the pond. A special get-away like old times. Not many of these left! Row or... View all property information
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From
$8,000
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1 / 23
4 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Dishwasher
  • TV
  • Dryer
  • Air Conditioning
  • Stereo System
  • Grill
  • DVD Player
  • Deck
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
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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From
$6,000
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1 / 29
6 Bedrooms, 2 Bathrooms, Sleeps 11
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Amenities & Details
  • Microwave
  • Dryer
  • Grill
  • Stereo System
  • TV
  • Dishwasher
  • Washer
  • DVD Player
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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From
$5,000
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1 / 19
5 Bedrooms, 2 Bathrooms, Sleeps 9
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Amenities & Details
  • DVD Player
  • Fireplace
  • Grill
  • Stereo System
  • Fax
  • TV
  • Deck
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
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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From
$1,250
Per Week
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1 / 13
2 Bedrooms, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Microwave
  • DVD Player
  • Deck
  • Grill
  • Water Views
  • Dishwasher
  • TV
  • Toaster
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Amenities and Features include... Menemsha, Waterview, Walk to beach Additional amenities include: coffee maker, fans - portable, lobster pot, food processor, washer / dryer, cd player, outside shower - enclosed, vacuum, outdoor furniture, ironing board. View all property information
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Suitability

  • Wheelchair access (1)
  • Elder access (2)
  • Suitable for children (14)
  • Pet friendly (9)
  • Smoking allowed (0)

Amenities

  • Grill (105)
  • Other outdoor space (96)
  • Internet (93)
  • Washer/Dryer (59)
  • Air Conditioning (27)
  • View all amenities