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$329

4 BR / 2 BA / Sleeps 8

Secluded Chilmark (Secluded-Chilmark-CH208) - Chilmark vacation rentals
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$329

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Secluded Chilmark (Secluded-Chilmark-CH208)

4 BR / 2 BA / Sleeps 8 | Quick view

Details

Secluded location on a cul de sac overlooking a private meadow with spreading oak trees. The traditional exterior welcomes you to our spacious contemporary. the main living area features a great room with fireplace which opens to a dining room and kitchen with an island eating bar. Off the great room is the main deck …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Porch
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$358

3 BR / 2 BA / Sleeps 6

Chilmark Rental With Private Beach! (Chilmark-Rental-With-Private-Beach!-CH236) - Chilmark vacation rentals
1 / 16

$358

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Chilmark Rental With Private Beach! (Chilmark-Rental-With-Private-Beach!-CH236)

3 BR / 2 BA / Sleeps 6 | Quick view

Details

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 romp and congregate …
  • Internet Access
  • Washing Machine
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  • Grill
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$386

3 BR / 2 BA / Sleeps 6

Charming Chilmark Rental Near West Tisbury Center! (Charming-Chilmark-Rental-Near-West-Tisbury-Center!-CH205) - Chilmark vacation rentals
1 / 20

Details

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 and simple, …
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  • Washing Machine
  • Clothes Dryer
  • Porch
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$572

3 BR / 3 BA / Sleeps 8

Chilmark Waterview With Beach And Tennis! (Chilmark--Waterview-With-Beach-And-Tennis!--CH216) - Chilmark vacation rentals
1 / 20

Details

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 private bath with …
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  • Fireplace
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  • Clothes Dryer
  • Deck
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$286

4 BR / 2 BA / Sleeps 8

Private Menemsha Rental Walk To Harbor, Town And Beach! (Private-Menemsha-Rental-Walk-To-Harbor,-Town-And-Beach!-CH237) - Chilmark vacation rentals
1 / 23

Details

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 maker, bakeware, …
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Porch
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$179

2 BR / 1 BA / Sleeps 4

FENNB - Menemsha, Waterview, Walk to beach - Chilmark vacation rentals
1 / 13

$179

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FENNB - Menemsha, Waterview, Walk to beach

2 BR / 1 BA / Sleeps 4 | Quick view

Details

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.
  • Ocean or water views
  • Phone / Internet
  • Deck
  • Grill
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$215

2 BR / 1 BA / Sleeps 4

1 / 23

$215

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THE POND HOUSE ON STONEWALL BEACH - CHIL JJAF-95GH

2 BR / 1 BA / Sleeps 4 | Quick view

Details

Luxurious beachfront living in Chilmark with sweeping water views of Stonewall Beach, Squibnocket Ridge, and Stonewall Pond. The Pond House sits directly on the intersection of Stonewall Beach and Pond, with water views throughout the house and across the large wraparound deck. Walls of windows and French doors frame …
  • Internet Access
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  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$383

3 BR / 3 BA / Sleeps 6

1 / 18

$383

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ITALA - North Slope Custom Home, Large Wrap Around Deck, WiFi

3 BR / 3 BA / Sleeps 6 | Quick view

Details

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 include exposed wood beams…
  • Internet Access
  • Deck
  • Grill
  • Dishwasher
  • Microwave
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$572

3 BR / 2 BA / Sleeps 6

1 / 22

$572

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DIETR - Menemsha Pond Waterfront, Mooring, Wifi, Central A/C

3 BR / 2 BA / Sleeps 6 | Quick view

Details

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 cedar. Central air and …
  • Waterfront
  • Ocean or water views
  • Phone / Internet
  • A/C or climate control
  • Deck
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$500

3 BR / 2 BA / Sleeps 8

1 / 35

$500

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HILL HOUSE ON STONEWALL POND - CHIL RALD-140

3 BR / 2 BA / Sleeps 8 | Quick view

Details

Hill House sits atop a bluff along the shores of Stonewall Pond with panoramic water views of the Pond and Stonewall Beach, as well as views over Quitsa Pond in the other direction. There is also access to Stonewall Beach, one of Chilmark's most prestigious private association beaches. Hill House is all about the view…
  • Internet Access
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  • Deck
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$593

4 BR / 2 BA / Sleeps 10

1 / 14

$593

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BERWD - Waterview, Walk to Menemsha Beach

4 BR / 2 BA / Sleeps 10 | Quick view

Details

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 a hill. New …
  • Ocean or water views
  • Internet Access
  • Deck
  • Grill
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$400

5 BR / 4 BA / Sleeps 12

1 / 21

$400

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HAUCJ -

5 BR / 4 BA / Sleeps 12 | Quick view

Details

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 amenities include: …
  • Phone / Internet
  • Deck
  • Grill
  • Dishwasher
  • Microwave
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$736

1 BR / 2 BA / Sleeps 3

1 / 14

$736

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YEOM1 - Waterview, Walk to Private Association South Shore Beach

1 BR / 2 BA / Sleeps 3 | Quick view

Details

"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 on a case by case …
  • Waterfront
  • Ocean or water views
  • Phone / Internet
  • Porch
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$643

5 BR / 4 BA / Sleeps 9

6 Reviews

$643

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Stunning Multi-Generational 5 BR Ocean View Home!

5 BR / 4 BA / Sleeps 9 | Quick view
“ Excellent ” 6 Reviews

Details

Reviews

(6)

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 sunshine and …
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(6)

Peaceful Beauty

Left on Jun 14, 2010 for a stay in May 2009

This home sits serenely on a small hill surrounded by fields. The floor plan is open and airy, with sunlight filling the rooms. Furnishings are comfortable. I especially love the gourmet kitchen and the view of the ocean from the living room. The lower level sleeping area is perfect for the kids, with the two master bedrooms on the main floor nice sized. The house is well appointed and organized…

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$358

4 BR / 3 BA / Sleeps 8

1 / 38

$358

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Lovely Beach Cottage In Menemsha! (Lovely-Beach-Cottage-In-Menemsha!-CH226)

4 BR / 3 BA / Sleeps 8 | Quick view

Details

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 spectacular sunsets…
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$572

3 BR / 3 BA / Sleeps 8

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$572

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Stonewall Pond- Le Nom

3 BR / 3 BA / Sleeps 8 | Quick view

Details

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 relaxation spots for…
  • Internet Access
  • Grill
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  • Microwave
  • Toaster
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$343

3 BR / 2 BA / Sleeps 6

1 / 24

Details

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 couple of minutes …
  • Ocean or water views
  • Phone / Internet
  • Deck
  • Grill
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$500

1 BR / 1 BA / Sleeps 4

1 / 24

$500

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Stonewall Pond-Boathouse

1 BR / 1 BA / Sleeps 4 | Quick view

Details

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 amenities include: …
  • Phone / Internet
  • Grill
  • Dishwasher
  • Microwave
  • Toaster
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$358

4 BR / 5 BA / Sleeps 8

1 / 36

Details

Featuring one of the most stunning water views and waterfront locations in Chilmark, The Beach House At Stonewall is just that. Stonewall Beach is directly at the property's edge. There is a private beach, and south-facing views of Stonewall Beach & Pond, Squibnocket Point, and on out to No Man's Land. Sitting atop a …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Patio
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$425

4 BR / 3 BA / Sleeps 8

1 / 16

$425

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TEELK - Menemsha Village Cottage, Walk to Menemsha Beach, A/C, WiFi

4 BR / 3 BA / Sleeps 8 | Quick view

Details

Ferry Tickets available for weeks 7/4-7/11, 7/11-7/18, 7/18-7/25 and 7/25-8/1 - 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…
  • Phone / Internet
  • A/C or climate control
  • Deck
  • Grill
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$893

4 BR / 3 BA / Sleeps 8

1 / 23

Details

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 Chilmark Community …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$643

3 BR / 2 BA / Sleeps 7

1 / 24

$643

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Stonewall Pond L\'Orca

3 BR / 2 BA / Sleeps 7 | Quick view

Details

The minute you enter this stunning property, you will be mesmerized by the ever changing sights and sounds of Stonewall Pond and Atlantic Ocean beyond. The views are unsurpassed and the house comfortable and casually elegant. A sweeping lawn leads to a private dock on the pond for swimming and kayaking and a path to …
  • Phone / Internet
  • Grill
  • Dishwasher
  • Microwave
  • Toaster
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$358

4 BR / 4 BA / Sleeps 8

1 / 21

$358

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CHILMARK RETREAT: MODERN STYLING, PRIVATE SETTING - CHIL MMAD-20

4 BR / 4 BA / Sleeps 8 | Quick view

Details

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 other muted tones, from…
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Porch
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$636

4 BR / 3 BA / Sleeps 8

1 / 18

Details

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 special rental. Part…
  • Private Beach
  • Ocean or water views
  • Phone / Internet
  • A/C or climate control
  • Porch
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$143

2 BR / 2 BA / Sleeps 4

1 / 11

$143

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329 - CHARMING WATERFRONT COTTAGE WITH WONDERFUL VIEWS OF THE ATLANTIC OCEAN

2 BR / 2 BA / Sleeps 4 | Quick view

Details

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 bedrooms and a …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Smoking allowed - ask
  • Suitable for children - over five
  • Suitable for the elderly - ask

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$279

3 BR / 2 BA / Sleeps 6

1 / 15

$279

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PERRG - A/C, WiFi

3 BR / 2 BA / Sleeps 6 | Quick view

Details

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.
  • Phone / Internet
  • A/C or climate control
  • Patio
  • Grill
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$604

3 BR / 2 BA / Sleeps 6

1 / 26

$604

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LEWID - Menemsha Waterfront, Magnificent Views and Private Location, WiFi

3 BR / 2 BA / Sleeps 6 | Quick view

Details

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 market, village …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Deck
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$571

3 BR / 2 BA / Sleeps 5

1 / 11

$571

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JUST OPENED UP! 8/16- 8/30, w/ ferry tix!

3 BR / 2 BA / Sleeps 5 | Quick view

Details

Light and bright with floor to ceiling sliding glass doors in every room. The views over the wetland to the pond are phenomenal. A truly magical spot to watch the glow of the Menemsha Sunset. A short walk to a private sandy beach for swimming, kayaking, or sunbathing. Recent improvements include new appliances, …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$429

5 BR / 3 BA / Sleeps 10

1 / 21

$429

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SUNSET FARM ON SQUIBNOCKET POND WITH SWEEPING WATER VIEWS - CHIL WWEL-18

5 BR / 3 BA / Sleeps 10 | Quick view

Details

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 Island. The house is …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,143

4 BR / 2 BA / Sleeps 2

1 / 24

Details

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 comfort and harmony. …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$686

3 BR / 2 BA / Sleeps 6

1 / 27

Details

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 downstairs features a media …
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Grill
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$358

3 BR / 2 BA / Sleeps 6

1 / 16

Details

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, comfortable house in a …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$786

5 BR / 3 BA / Sleeps 10

1 / 19

Details

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 chairs, chaises lounges…
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,072

4 BR / 3 BA / Sleeps 8

1 / 23

Details

This Chilmark contemporary home offers views over Chilmark Pond to the South Shore. There are four bedrooms three full baths an open floor plan that includes a kitchen, living room and dining room that open up to decks and additional living space. Includes canoe to take over the pond to beautiful south shore beach. …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,072

4 BR / 4 BA / Sleeps 8

1 / 17

$1,072

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Quansoo area retreat 119397

4 BR / 4 BA / Sleeps 8 | Quick view

Details

Stunning Quansoo/Great Pond setting. Lots of room to roam and explore at this waterfront property, which includes access to Quansoo beach, a private dock for launching your kayaks from, and a relaxing setting from which to take in the beautiful views this property has to offer. Air conditioned throughout, screened in …
  • Waterfront
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$429

3 BR / 3 BA / Sleeps 8

1 / 24

$429

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Waterview Home Overlooking Stonewall Pond 116920

3 BR / 3 BA / Sleeps 8 | Quick view

Details

Beautifully furnished and decorated home with all the amenities. Bright, airy two story interior, lovely views over Stonewall Pond to the barrier beach beyond, great sunsets via roof deck. Two story fireplace, recently renovated kitchen with all new appliances and granite tile counters. Complete privacy, cedar filled …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Porch
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$358

1 BR / 1 BA / Sleeps 4

1 / 20

$358

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Private Boathouse at Edge of Stonewall Pond 116925

1 BR / 1 BA / Sleeps 4 | Quick view

Details

Adorable, private boathouse at the edge of Stonewall Pond. Wrap around deck provides gorgeous views (as well as sound effects) of the pond and the barrier beach beyond, great for swimming! Perfect for a small family or a romantic getaway. An idyllic island retreat. Additional amenities include: dock/boat-slip, …
  • Waterfront
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Porch
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,143

4 BR / 3 BA / Sleeps 8

1 / 21

$1,143

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Spectacular Home with Private Pool & Tennis 116946

4 BR / 3 BA / Sleeps 8 | Quick view

Details

A spectacular Chilmark estate located on 6.9 acres complete with private pool and tennis courts. An updated master bedroom and bathroom will soothe you after a busy day at the beach. Comfortable furnishings paired with state-of-the-art appliances make this a truly magnificent vacation experience. Additional …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,429

4 BR / 3 BA / Sleeps 10

1 / 20

$1,429

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Waterfront on Quitsa Pond with Dock 116754

4 BR / 3 BA / Sleeps 10 | Quick view

Details

Wonderful four bedroom home directly on Quitsa Pond with private deep water dock. One bedroom guest cottage included in rental. Additional amenities include: dock/boat-slip, smoke free, pets considered, lobster pot, 1st floor bedroom, 1 king bed(s), 8 dining capacity, 1 double bed(s), 4 single bed(s), ironing board.
  • Waterfront
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$179

2 BR / 1 BA / Sleeps 4

1 / 9

$179

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Menemsha Sunsets on the Deck 116552

2 BR / 1 BA / Sleeps 4 | Quick view

Details

Nice two bedroom cottage located in the heart of Menemsha. Watch the beautiful sunsets from the deck while dining. Five minute walk to beach, fish market or quaint shops in this fishing village. Additional amenities include: coffee maker, smoke free, 4 dining capacity, lobster pot, 1 trundle(s), vacuum cleaner, …
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$715

2 BR / 1 BA / Sleeps 8

1 / 14

$715

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Chilmark - UpIsland Two Bedroom Guest Cottage 120760

2 BR / 1 BA / Sleeps 8 | Quick view

Details

Chilmark family retreat. Overlooking the expansive meadows of Grey Barn s 62 acres of protected farmland. 2 bedrooms with an additional sleeping loft. Exclusive up-island beach access to Squibnocket and Lucy Vincent. Additional amenities include: coffee maker, smoke free, pets considered, 4 dining capacity, lobster …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$2,143

6 BR / 5 BA / Sleeps 8

1 / 27

$2,143

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High on a Hill, Walk to Squibnocket Beach 116957

6 BR / 5 BA / Sleeps 8 | Quick view

Details

Exceptional, private home set high on a hill with views of Menemsha Pond and Atlantic Ocean. Great outdoor space for entertaining and/or relaxing on the patio as well as deck areas. Beautifully landscaped setting with gardens and stonework throughout yard. Post and beam, tastefully furnished with hardwood floors …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$3,572

4 BR / 3 BA / Sleeps 10

1 / 11

$3,572

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Chilmark - 123611

4 BR / 3 BA / Sleeps 10 | Quick view

Details

N/A
  • Waterfront
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,429

3 BR / 4 BA / Sleeps 6

1 / 21

$1,429

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Beautifully Restored Antique Cape 113602

3 BR / 4 BA / Sleeps 6 | Quick view

Details

Beautifully renovated and restored antique Cape situated in Chilmark on two ponds. Three bedroom home plus loft area. Tastefullly furnished throughout with full modern amenities. Living room, dining room as well as an eat-in kitchen. Includes a game room with pool table and sitting area for relaxing and enjoying …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Patio
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$358

4 BR / 3 BA / Sleeps 8

1 / 23

$358

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Menemsha Sunsets, Harbor and Beach 113585

4 BR / 3 BA / Sleeps 8 | Quick view

Details

Charming, remodeled in 2000, this is a seaside cottage overlooking Menemsha Harbor and beach. Bright and open interior with upscale details, the house is very comfortable. Master suite upstairs with deck and views of harbor, beach and sunsets. Backyard is private with outdoor deck and screened in porch. Guest cottage …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Porch
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$929

6 BR / 5 BA / Sleeps 8

1 / 26

$929

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Expansive Views of Farmland and Ocean 116399

6 BR / 5 BA / Sleeps 8 | Quick view

Details

Wonderful, Vineyard oversized Cape with expansive views of picturesque farmland (Keith Farm) and Atlantic Ocean. Separate main house and guest house allow for comfortable space between guests and families. Extremely charming home with all necessary amenities; beautifully renovated kitchen. Very close to Chilmark …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Porch
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$358

4 BR / 3 BA / Sleeps 8

1 / 13

$358

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Chilmark - Hillside retreat 119742

4 BR / 3 BA / Sleeps 8 | Quick view

Details

Located on the North side of Chilmark, this contemporary getaway offers a wide open living space with vaulted ceilings, stylish furnishings, a spacious deck and a stunning widow’s watch with water views. Completely renovated in 2012, this home feels like new and features a brand new kitchen with top of the line …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Deck
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$286

4 BR / 5 BA / Sleeps 8

1 / 26

$286

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Elegant Waterfront Beach House Retreat 116330

4 BR / 5 BA / Sleeps 8 | Quick view

Details

Sunrise from the ocean, sunset over Stonewall Pond and view towards Squibnocket Beach. Old Vineyard look and feel, an elegant and comfortable beach house with landscaped gardens. Recently built 500 sq ft addition includes ground floor MBR suite offering full amenities. Services include: cleaning 3X s/week, …
  • Waterfront
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,072

3 BR / 2 BA / Sleeps 6

1 / 20

$1,072

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Waterfront Contemporary on Chilmark Pond 116771

3 BR / 2 BA / Sleeps 6 | Quick view

Details

Waterfront contemporary home situated on eight secluded acres in Upper Chilmark Pond, great views of pond to ocean. Explore the ponds in one of the boats included. Relax and enjoy the spacious outdoor deck. Additional amenities include: dock/boat-slip, coffee maker, smoke free, ipod dock station, lobster pot, ferry …
  • Waterfront
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1

4 BR / 3 BA / Sleeps 8

1 / 17

$1

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Set High on a Hill, Enjoy Menemsha Sunsets 116929

4 BR / 3 BA / Sleeps 8 | Quick view

Details

Set high on the hill, have your own private viewing of the spectacular Menemsha sunset from this multi-level saltbox home. Walk to Menemsha beach or village in just minutes. Bright, cheerful rooms with water views from nearly every room is sure to make your stay an unforgettable experience. Additional amenities …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
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