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$329

4 BR / 2 BA / Sleeps 8

Secluded Chilmark (Secluded-Chilmark-CH208) - Chilmark vacation rentals
1 / 4

$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
  • Clothes Dryer
  • 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, …
  • Internet Access
  • 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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$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 …
  • Internet Access
  • Fireplace
  • Washing Machine
  • 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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$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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$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
  • 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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$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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$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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$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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$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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$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
  • 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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$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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$572

3 BR / 3 BA / Sleeps 8

1 / 31

$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
  • Dishwasher
  • 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 / 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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$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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$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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$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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$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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$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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$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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$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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$528

3 BR / 4 BA / Sleeps 9

3 Reviews

$528

Inquire

Celebrity Owned Hilltop Watervew with Hot Tub

3 BR / 4 BA / Sleeps 9 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

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 day. Those days show …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(3)

Fantastic Family Retreat !

Left on Apr 18, 2011 for a stay in September 2009

Our extended family enjoyed a wonderful reunion here. The terrace was the site of some wonderful dinners! We enjoyed the hot tub almost every evening and some mornings as well. It was a little off of the main road but well worth the time to get to.
The beaches were absolutely splendid and we were surprised the water was so warm yet.
We are still talking about it hoping to return.

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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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$2,215

5 BR / 4 BA / Sleeps 8

1 / 13

Details

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.
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Smoking allowed - ask
  • Suitable for children - over five
  • Suitable for the elderly - 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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$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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$215

2 BR / 1 BA / Sleeps 4

1 / 11

$215

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UpIsland Cottage Nestled in the Woods 116958

2 BR / 1 BA / Sleeps 4 | Quick view

Details

Nicely renovated cottage nestled in the woods, enjoy the peace and quiet of up-island living. Clean, open interior living area, newly furnished with fully equipped kitchen. Enclosed outdoor shower a must for days at the beach. Perfect getaway cottage, sure to please. Additional amenities include: coffee maker, smoke …
  • Internet Access
  • 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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$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

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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$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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$150

4 BR / 2 BA / Sleeps 9

1 / 10

$150

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Chilmark Contemporary Cape with Access to Beaches 116588

4 BR / 2 BA / Sleeps 9 | Quick view

Details

Spacious and comfortably furnished contemporary Cape is conveniently located between Chilmark and West Tisbury. House is fully equipped, open living area with cathedral ceilings, wood floors, operable skylights, large outdoor deck and separate family room with sleeper sofa. Private setting with access to Chilmark …
  • Internet Access
  • Housekeeping Optional
  • 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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$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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$700

5 BR / 5 BA / Sleeps 9

1 / 21

$700

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Spacious Five Bedroom with Sweeping Views 116752

5 BR / 5 BA / Sleeps 9 | Quick view

Details

Relax and enjoy sweeping views of the South Shore from the upper deck balcony. Sprawling interior design provides an open and comfortable space, ideal for family living. A fully loaded kitchen with top of the line appliances, perfect for entertaining. Unwind in the screened-in porch which overlooks an amazing yard. …
  • Internet Access
  • Fireplace
  • 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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$500

3 BR / 2 BA / Sleeps 8

1 / 20

$500

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Beautiful Setting with Spectacular Views 116921

3 BR / 2 BA / Sleeps 8 | Quick view

Details

Beautiful Chilmark setting, located on Stonewall Pond with spectacular waterviews! The east offers views of Stonewall Pond to the Atlantic ocean. The west offers views of Quitsa Pond to Menemsha Pond. Great outdoor deck perfect for relaxing and/or outdoor entertaining. Large sweeping lawn and mature landscaping …
  • 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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$358

4 BR / 4 BA / Sleeps 16

1 / 15

$358

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Spacious Contemporary in Wooded Hillside 114865

4 BR / 4 BA / Sleeps 16 | Quick view

Details

Spacious, contemporary Cape-style home with a wrap around deck tucked into a wooded hilllside on 3.8 acres. Distant waterviews of Cape Higon and Vineyard Sound. The overall design and layout with the 4 bedrooms and 2 lofts allows space for extended family get-togethers and special occasions. Additional amenities …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Porch
  • 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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$1,429

5 BR / 4 BA / Sleeps 10

1 / 20

$1,429

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Located in Desirable Squibnocket Farm 116302

5 BR / 4 BA / Sleeps 10 | Quick view

Details

Squibnocket Farm is comprised of over 325 acres of beautiful rolling land nestled between Squibnocket Pond and the Atlantic Ocean. A very exclusive island location with only a few homes throughout the farm. Private access to a world-class beach and Squibnocket Pond - a rare combination of rural habitats. The home …
  • Internet Access
  • Fireplace
  • 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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$1,472

5 BR / 5 BA / Sleeps 10

1 / 29

$1,472

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WINGR

5 BR / 5 BA / Sleeps 10 | Quick view

Details

Take me home country road....to the place I belong......Wingate Roost is home............and down a beautiful country road. Set among the hills of Squibnocket with views of the pond and the Atlantic this unpretentious home will envelope you in its understated elegance. Windows everywhere let the light and the hypnotic…
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Phone / Internet
  • Outdoor Dining Area
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$715

5 BR / 3 BA / Sleeps 9

1 / 19

$715

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Bluff House, Waterfront with Private Beach 114875

5 BR / 3 BA / Sleeps 9 | Quick view

Details

Wonderful Vineyard cape situated on one of the most gorgeous spots on the island. The views are phenomenal in any direction and the house is cozy and charming. Large stretch of gorgeous, sandy and private beach. One of the most breathtaking spots on the island! Additional amenities include: dock/boat-slip, coffee …
  • 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

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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$2,572

4 BR / 2 BA / Sleeps 7

1 / 24

$2,572

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Squibnocket Farm Beautiful Converted Barn 116303

4 BR / 2 BA / Sleeps 7 | Quick view

Details

Beautiful converted barn located in exclusive Squibnocket Farm. Access to one of the Vineyards most pristine and private ocean beaches. This home has the original exposed beams and floor to ceiling windows offering spectacular views of the surrounding meadows, ocean, pond and gardens. Balconies and lofts overlook the …
  • Waterfront
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$1,472

5 BR / 5 BA / Sleeps 10

1 / 27

$1,472

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Chilmark - Stunning Waterviews in Squibnocket 116998

5 BR / 5 BA / Sleeps 10 | Quick view

Details

Located in one of the most exclusive associations on the Vineyard, this five bedrooms home offers some of the most stunning water views the island has to offer. This home includes spacious decks, vaulted ceilings, and all the amenities one expects in a premier property. Tenants have access to both the association and …
  • 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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$1,072

3 BR / 3 BA / Sleeps 8

1 / 27

$1,072

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Peaceful Setting Overlooking Meadow & Pond 116572

3 BR / 3 BA / Sleeps 8 | Quick view

Details

Peaceful up-island setting on eight acres overlooking meadow and pond. The property borders 46 acres of conservation land in back, and approximately 25 acres in front. Open, bright, sun-filled living area with hardwood flooring throughout the home. Tastefully decorated and comfortably furnished. Fully equipped kitchen…
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
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