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House Rentals in Chilmark, MA

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Travelers to Chilmark are booking May dates now. Secure your vacation rental today, and have the perfect trip.
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From
$345
Per Night
1 / 10
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3 Bedrooms, 3 Bathrooms, Sleeps 6
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From
$900
Per Night
1 / 30
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5 Bedrooms, 4 Bathrooms, Sleeps 12
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From
$4,150
Per Week
1 / 10
4 Bedrooms, 2 Bathrooms, Sleeps 8
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From
$8,500
Per Week
1 / 10
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Deck
  • Grill
  • Dishwasher
  • Stereo System
  • Water Views
  • VCR
  • TV
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
High in the hills of peaceful Chilmark with distant panoramic waterviews, this four bedroom impeccably maintained house with in gound pool is surrounded by beautifully landscaped grounds. Expansive decks invite you to make the most of summer living. Amenities and Features include... Chilmark,... View all property information
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From
$2,800
Per Week
1 / 21
5 Bedrooms, 4 Bathrooms, Sleeps 12
Details Make Inquiry
Amenities & Details
  • Microwave
  • VCR
  • Ceiling Fans
  • Grill
  • Dishwasher
  • Satellite TV
  • Toaster
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
An adward 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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From
$5,500
Per Week
1 / 18
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • TV
  • Grill
  • Dishwasher
  • Dryer
  • Fireplace
  • Patio
  • VCR
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Expansive distant waterviews overlooking Vineyard Sound on three and a half acre property. Located in desirable Spring Point, this 40 home association is accessed by a private, well maintained dirt roads with 40 acres of common land consisting of nature trails and a private beach on the Sound. This... View all property information
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From
$1,950
Per Week
1 / 15
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
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
$2,500
Per Week
1 / 8
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Satellite TV
  • DVD Player
  • Stereo System
  • Fax
  • Dishwasher
  • TV
  • Patio
  • VCR
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Main House on the same property may be occupied by Owner or another Tenant. Peaceful private setting on one of the most beautiful areas on the South Shore. Amenities and Features include... Waterfront Guest House, Private Beach Additional amenities include: coffee maker, internet - ethernet... View all property information
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From
$4,000
Per Week
1 / 22
4 Bedrooms, Sleeps 8
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Fireplace
  • Satellite TV
  • Grill
  • Water Views
  • Microwave
  • Waterfront
  • Deck
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Chilmark waterfront rental home located on Quitsa Pond with views across Quitsa and Menemsha ponds out to the Elizabeth Islands. This martha's vineyard rental property offers private dock, mooring along with access to small beach area just down the path on Clam Point Cove. Named appropriately, it... View all property information
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5 of 5 stars Reviewed September 3, 2014
Our family thoroughly enjoyed our week at the Mayhew home in Chilmark. We rented kayaks for some boating right off the private pier, picked clams, swam off the docked and cooked...
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From
$2,000
Per Week
1 / 12
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Internet Access
  • DVD Player
  • Stereo System
  • VCR
  • TV
  • Dishwasher
  • Ceiling Fans
  • Deck
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Charming newly renovated cottage features large screened porch and private deck. Porch is fully furnished for dining and relaxing. Ten minutes to famous Lucy Vincent Beach and the same distance to West Tisbury village and Alley's General Store. Amenities and Features include... Screened Porch,... View all property information
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From
$2,500
Per Week
1 / 23
4 Bedrooms, 4 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Satellite TV
  • TV
  • Fax
  • VCR
  • Deck
  • Microwave
  • Ceiling Fans
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Ocean Front Splendor in an elegant and comfortable beach house. Sunrise from the ocean, sunset over the adjoining 13-acre Sheriff's Meadow Foundation conservation preserve. Walk to your private beach. New 500 square foot addition, added for summer 2008, includes ground floor Master Bedroom suite,... View all property information
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From
$4,450
Per Week
1 / 18
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Water Views
  • Grill
  • Satellite TV
  • Microwave
  • VCR
  • DVD Player
  • Porch
  • Air Conditioning
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Panoramic South Shore ocean vista from this outstanding private rental home. Less than one mile to famous Lucy Vincent Beach. Owner also offers private beach rights to the south side via canoe or kayak (provided by owners.) Classic style and modern luxury combine to make this family retreat a very... View all property information
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From
$2,680
Per Week
1 / 18
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Satellite TV
  • TV
  • Stereo System
  • DVD Player
  • Microwave
  • Grill
  • Internet Access
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Contemporary Post and Beam home, private location, bounded by large oaks and stone walls. Enjoy this impeccably maintained 3 bedroom, 3 bath home. Custom designed and featuring a chef's kitchen. The cathedral ceiling great room is open to the spacious dining and kitchen area. Custom features... View all property information
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From
$6,200
Per Week
1 / 9
4 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Water Views
  • TV
  • Dishwasher
  • Beach Or Lakeside...
  • Satellite TV
  • Number Of Bedrooms
  • Waterfront
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Black Smith Valley. Classic Cape overlooking acres of pastoral meadows and across Squibnocket Pond to open ocean. Immaculate home accented with country antiques and comfortable beds with linens provided. Walk to Squibnocket Beach or drive to Lucy Vincent Beach or make use of the private association... View all property information
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From
$600
Per Night
1 / 64
Payment Protection
3 Bedrooms, 4 Bathrooms, Sleeps 9
Details Reviews (3) Make Inquiry
Amenities & Details
  • Stove
  • DVD Player
  • Garage
  • Grill
  • Fireplace
  • Microwave
  • Washer
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Sprawling Hilltop Glass House admits views and entertains peace from every angle. Large south facing stone terrrace has hot tub and large table to enjoy guests and family. Please note: The calendar may not display the 1st and last dates of booked property as this house may turn over on the same... View all property information
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5 of 5 stars Reviewed August 15, 2013
This was a fabulous family retreat. Plenty of bathrooms, very comfortable beds, and a great outdoor patio for grilling or lounging. We hope to come back next year!
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From
$5,150
Per Week
1 / 31
5 Bedrooms, 4 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Porch
  • Grill
  • Satellite TV
  • Dishwasher
  • TV
  • Deck
  • Air Conditioning
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
MVVR EXCLUSIVE: Spectacular 5 bedroom, 4.5 bath retreat. Lovely distant waterviews overlooking the South Shore. Hilltop setting with privacy and a five minute drive to Lucy Vincent Beach. This spacious custom home has been decorated by one of the island's premier professionals. A combination of... View all property information
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From
$3,500
Per Week
1 / 11
5 Bedrooms, 3 Bathrooms, Sleeps 12
Details Make Inquiry
Amenities & Details
  • Grill
  • Ceiling Fans
  • Deck
  • DVD Player
  • Microwave
  • TV
  • Dishwasher
  • Fax
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Spacious, well furnished and equipped, comfortable home in quiet neighborhood on 3 acres. Two master bedrooms, one on each floor; pool table. Within walking distance (about 1 mile) to small North Shore beach (Great Rock Bite). Three mile drive to Lucy Vincent Beach. Amenities and Features... View all property information
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From
$4,150
Per Week
1 / 14
4 Bedrooms, 2 Bathrooms, Sleeps 10
Details Make Inquiry
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
$2,725
Per Week
1 / 14
5 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Deck
  • TV
  • Internet Access
  • Ceiling Fans
  • DVD Player
  • Microwave
  • Dishwasher
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Classic coastal cottage remodeled in 2000. Charming open and sunny interior feautres 3 bedrooms and 2 baths in the main house. 2nd level Master bedroom opens onto private deck with views of Menemsha Harbor. Seperate guest cottage has Qeen bedroom and a full bath. Outdoor spaces for your vacation... View all property information
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From
$643
Per Night
1 / 45
Payment Protection
5 Bedrooms, 4 Bathrooms, Sleeps 9
Details Reviews (6) Make Inquiry
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
$4,000
Per Week
1 / 22
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • VCR
  • Deck
  • Waterfront
  • Air Conditioning
  • Grill
  • Internet Access
  • Satellite TV
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Steps from Menemsha Pond – look across the ever-changing surface of the water to Menemsha, the Creek, the Lobsterville dunes, Vineyard Sound and the Elizabeth Islands. Magnificent sunsets from the living room. This cathedral-ceiling Modernist masterpiece is constructed entirely of Western red... View all property information
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From
$10,000
Per Week
1 / 32
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • DVD Player
  • Grill
  • Air Conditioning
  • Patio
  • Fax
  • Deck
  • Microwave
  • VCR
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
7 acre Luxury Chilmark Estate in an Idyllic setting of stone walls, perennial gardens and orchards. Private pool and hot tub surrounded by a large deck and bordered by tiered rose gardens. A regulation tennis court is set a short walk across the meadow. There is a beautiful natural pond on the... View all property information
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From
$2,250
Per Week
1 / 16
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Porch
  • Grill
  • Deck
  • TV
  • Microwave
  • Water Views
  • Satellite TV
  • Stereo System
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Charming Chilmark cottage with panoramic South Shore waterviews. A five minute stroll to South surf beach. Private tennis courts shared with owners and other tenants. Access to Stonewall Pond for launching canoes and kayaks. Seaside cottage charm has been maintained throughout with tung and groove... View all property information
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From
$2,650
Per Week
1 / 11
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Internet Access
  • Satellite TV
  • DVD Player
  • Microwave
  • Deck
  • Dishwasher
  • Grill
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Lovely 3 bedroom 2 bath home. All new kitchen and baths. Completely renovated - lots of glass for a light filled interior. This lovely home in a private setting is surrounded by mature Holly trees, Laurel and attractive native shrubs. 1 mile to Alley's General Store. 10 minute drive to Lucy Vincent... View all property information
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From
$2,500
Per Week
1 / 23
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (1) Make Inquiry
Amenities & Details
  • Telephone
  • Deck
  • Grill
  • Internet Access
  • Dishwasher
  • Stereo System
  • DVD Player
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • 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 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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From
$5,150
Per Week
1 / 14
1 Bedroom, 2 Bathrooms, Sleeps 3
Details Make Inquiry
Amenities & Details
  • DVD Player
  • Deck
  • TV
  • Water Views
  • Grill
  • Microwave
  • Satellite TV
  • Porch
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
'The Little House' on the beach. Two minute stroll to South surf beach. Incredible views from sunrise to sunset. Private tennis courts shared with owners and other tenants. Access to Stonewall Pond for launching canoes and kayaks. This wonderful cottage is a one of a kind. A pet will be considered... View all property information
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From
$2,975
Per Week
1 / 16
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Satellite TV
  • Microwave
  • DVD Player
  • Air Conditioning
  • Stereo System
  • # Of Bathrooms
  • Dishwasher
  • Internet Access
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Charming 4 bedroom, 3 bath traditional summer cottage. Enjoy this impeccably maintained summer home surrounded by a mature landscaped yard with lots of flowering shrubbery. A large deck offers privacy and a wonderful setting for those summer barbeques. A modern well equipped kitchen opens to the... View all property information
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From
$2,625
Per Week
1 / 24
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Blender
  • TV
  • Number Of Bedrooms
  • Dishwasher
  • Deck
  • Microwave
  • Iron
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Pristine modern summer cottage with distant views of Lucy Vincent Beach, privately nestled on historic Eddy Farm, hillside, off of South Rd. This light filled home with acres of privacy is the perfect retreat for those looking for a long term summer stay in Chilmark with Lucy Vincent Beach just a... View all property information
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From
$1,625
Per Week
1 / 10
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Deck
  • # Of Bathrooms
  • Satellite TV
  • Microwave
  • Grill
  • Water Views
  • Porch
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Located in the picturesque village of Menemsha. Walk to Menemsha public beach. Amenities and Features include... Picturesque Menemsha, Walk to Menemsha Beach Additional amenities include: coffee maker, washer / dryer, cd player, landscaped, outside shower - enclosed, outdoor furniture. View all property information
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From
$2,000
Per Week
1 / 22
4 Bedrooms, 5 Bathrooms, Sleeps 8
Details Reviews (1) Make Inquiry
Amenities & Details
  • DVD Player
  • TV
  • Microwave
  • Dryer
  • VCR
  • Grill
  • Fax
  • Stereo System
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • 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
$10,700
Per Week
1 / 34
5 Bedrooms, 5 Bathrooms, Sleeps 10
Details Make Inquiry
Amenities & Details
  • Fax
  • Deck
  • TV
  • Patio
  • Ceiling Fans
  • Microwave
  • Internet Access
  • Air Conditioning
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Dramatic ocean views, idyllic one of a kind location in gated community, private ocean beaches are but a few of the desirable features of this all new 5 bedroom, 5 bath contemporary home, set in one of the most Idyllic landscapes on Martha's Vineyard. Situated hilltop this gorgeous summer home... View all property information
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From
$8,500
Per Week
1 / 23
6 Bedrooms, 4 Bathrooms, Sleeps 10
Details Make Inquiry
Amenities & Details
  • Deck
  • Patio
  • Dishwasher
  • DVD Player
  • Fax
  • Stereo System
  • VCR
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Contemporary Home commands one of Martha's Vineyard's most spectacular views overlooking the Elizabeth Islands and Vineyard Sound. Breathtaking sunsets. Outdoor patios and deck and multiple living areas provide many options for family gatherings or quiet times. Amenities and Features include...... View all property information
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From
$3,800
Per Week
1 / 29
4 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Microwave
  • Ceiling Fans
  • VCR
  • Dishwasher
  • TV
  • Air Conditioning
  • Deck
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This incredible home is furnished with one of a kind artisan wood and textile pieces, as well as Donghia soft seating and is filled with art, vintage stain glass, antiques, and one of kind artisan furniture. The ocean view is spectacular from the great room (living room, dining area and kitchen,... View all property information
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From
$3,800
Per Week
1 / 24
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Internet Access
  • # Of Bathrooms
  • Waterfront
  • Dishwasher
  • Deck
  • Water Views
  • Microwave
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Stunning Waterfront Views. Kayak or swim across the pond to Stonewall Beach or just relax on the expansive decks overlooking the water. This is an immaculate older home, very comfortably furnished with 3 bedrooms and 2 baths. High Speed Internet. Renters can tie their dinghy to the house dock to... View all property information
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From
$3,000
Per Week
1 / 21
5 Bedrooms, 3 Bathrooms, Sleeps 10
Details Make Inquiry
Amenities & Details
  • Patio
  • Washer
  • VCR
  • Porch
  • Dishwasher
  • Grill
  • DVD Player
  • Dryer
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
$1,175
Per Week
1 / 8
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Deck
  • # Of Bathrooms
  • Satellite TV
  • Guest Count
  • Toaster
  • Grill
  • DVD Player
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Amenities and Features include... Menemsha Additional amenities include: coffee maker, fans - portable, lobster pot, washer / dryer, landscaped, porch - screened, outside shower - enclosed, phone ld block, outdoor furniture, ironing board. View all property information
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From
$3,825
Per Week
1 / 26
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Satellite TV
  • TV
  • Waterfront
  • Internet Access
  • Microwave
  • Grill
  • Dishwasher
  • VCR
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This quintessential Chilmark home has been impeccably maintained and continuously updated. The dining and living areas open to a wrap around deck. Enjoy spectacular water views and sunsets from just about every room in the house. Stroll to the beach and Menemsha village where you will find the fish... View all property information
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From
$2,925
Per Week
1 / 24
4 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • DVD Player
  • Internet Access
  • # Of Bathrooms
  • TV
  • VCR
  • Microwave
  • Water Views
  • Deck
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Casual immaculately clean in picturesque Menemsha, Chilmark waterfront. Beautiful views. A short stroll to the beach, fish market, boutiques, fishing, and shore dinners. Guest House - Main House on property nearby may be occupied by Tenants or Owner. Amenities and Features include...... View all property information
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From
$2,800
Per Week
1 / 25
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Ceiling Fans
  • Fax
  • Microwave
  • Grill
  • Satellite TV
  • VCR
  • Deck
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Tastefully furnished and decorated with antiques and art. This Chilmark summer home is an original Yankee Barn located off South Road that has all the accouterments for summer entertaining. The post and beam structure features a beautiful cathedral living room brightened by southern light; has... View all property information
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From
$3,000
Per Week
1 / 26
5 Bedrooms, 3 Bathrooms, Sleeps 9
Details Make Inquiry
Amenities & Details
  • Patio
  • Dishwasher
  • Fax
  • DVD Player
  • VCR
  • Grill
  • Microwave
  • Deck
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
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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From
$6,750
Per Week
1 / 16
4 Bedrooms, 3 Bathrooms, Sleeps 7
Details Make Inquiry
Amenities & Details
  • TV
  • Dishwasher
  • VCR
  • Ceiling Fans
  • DVD Player
  • Deck
  • Grill
  • Fax
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Gorgeous Chilmark Home completely private, large acreage. Exterior features large deck, screened porch and large open porch with lovely vistas across the picturesque yard. The interior hosts a large living room with walls of glass and opens to the deck. Family room, den, light filled, and again,... View all property information
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From
$1,250
Per Week
1 / 13
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Inquiry
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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From
$3,300
Per Week
1 / 24
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Porch
  • Satellite TV
  • Grill
  • TV
  • VCR
  • Dishwasher
  • Microwave
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Gorgeous Views of Stonewall Pond from this immaculate 4 bedroom three bath home. Cathedral ceilings add to the spacious feeling of this contemporary home and the open kitchen, living and dining areas provide the perfect space for your summer vacation. There is a spacious loft area that opens to the... View all property information
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From
$4,500
Per Week
1 / 18
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Dishwasher
  • Microwave
  • Ceiling Fans
  • TV
  • Air Conditioning
  • Deck
  • Satellite TV
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Amenities and Features include... Quansoo (with private beach key), Central Air, Waterview, Waterfront Additional amenities include: coffee maker, internet - ethernet cord required, pets considered, lobster pot, washer / dryer, cd player, porch - screened, outside shower - enclosed, private... View all property information
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From
$5,000
Per Week
1 / 19
5 Bedrooms, 2 Bathrooms, Sleeps 9
Details Make Inquiry
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
$20,700
Per Week
1 / 38
Studio, 3 Bathrooms, Sleeps 10
Details Make Inquiry
Amenities & Details
  • Water Views
  • Dishwasher
  • Microwave
  • Stereo System
  • Deck
  • Internet Access
  • Grill
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Expansive views of Chilmark Pond and the Atlantic Shoreline. Deeded access to pond, dock and private ocean beach (please inquire for more information). Newly completed 5400 square foot luxury home with ... multiple decks overlooks the masterfully landscaped grounds, stone walls, and ocean views... View all property information
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From
$4,850
Per Week
1 / 6
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • DVD Player
  • Internet Access
  • Grill
  • Dishwasher
  • Water Views
  • # Of Bathrooms
  • Microwave
  • Toaster
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
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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From
$2,700
Per Week
1 / 17
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Dishwasher
  • Internet Access
  • TV
  • Microwave
  • Porch
  • Waterfront
  • VCR
  • Stereo System
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
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 include... Waterfront, Hi Speed Internet Additional... View all property information
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From
$7,200
Per Week
1 / 30
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Dishwasher
  • Grill
  • Air Conditioning
  • Patio
  • Porch
  • DVD Player
  • Fax
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Outstanding private rental home nestled on 7.2 private acres in the seaside community of Chilmark on the Island of Martha's Vineyard, features a key to Quansoo Beach, one of the most beautiful private association beaches on the island. Warmth, comfort and charm await you and your family in this air... View all property information
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From
$2,700
Per Week
1 / 20
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
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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Suitability

  • Wheelchair access (1)
  • Elder access (2)
  • Suitable for children (0)
  • Pet friendly (8)
  • Smoking allowed (0)

Amenities

  • Other outdoor space (166)
  • Internet (160)
  • Grill (159)
  • Washer/Dryer (103)
  • Air Conditioning (54)
  • View all amenities