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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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$343

3 BR / 2 BA / Sleeps 6

WHITP - 2 week minimum stay, Pristine Hilltop Ocean View, 1.2 Miles to Lucy Vincent Beach, Long Term Summer Rental - Chilmark vacation rentals
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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$358

4 BR / 3 BA / Sleeps 8

Menemsha Sunsets, Harbor and Beach 113585 - Chilmark vacation rentals
1 / 23

$358

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Menemsha Sunsets, Harbor and Beach 113585

Chilmark house
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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$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)

Chilmark house
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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$143

3 BR / 3 BA / Sleeps 8

Wonderful Three Bedroom Up-Island Retreat 116582 - Chilmark vacation rentals
1 / 14

$143

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Wonderful Three Bedroom Up-Island Retreat 116582

Chilmark house
3 BR / 3 BA / Sleeps 8 | Quick view

Details

This wonderful three bedroom up-island retreat, is the perfect summer vacation home, with lots of room to spread out. The master bedroom on the first floor offers great light in the morning sun with ensuite bathroom. The second floor with two bedrooms, shared bathroom and small office area on the second floor offers a…
  • 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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$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

Chilmark house
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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$475

6 BR / 2 BA / Sleeps 14

1 / 20

Details

A large rambling old family home where memories are made. The extended family can all join in a vacation full of laughter and play. The grounds are full of places for hide-and-go-seek. Privately set on Middle Road in the woods yet bathed in sunlight. The house has a string of bedrooms for all the family members to …
  • Internet Access
  • Washing Machine
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  • Deck
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$286

4 BR / 2 BA / Sleeps 8

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

PreviousNext property

$358

3 BR / 2 BA / Sleeps 6

1 / 16

$358

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

Chilmark house
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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$286

3 BR / 2 BA / Sleeps 7

1 / 17

$286

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Waterview Cottage, Short Walk to Menemsha 116972

Chilmark house
3 BR / 2 BA / Sleeps 7 | Quick view

Details

Charming cottage with water view just steps into Menemsha. Great outdoor deck, new kitchen - everything recently updated. Wonderful antiques for decoration and top quality furnishings throughout. Additional amenities include: coffee maker, smoke free, 6 dining capacity, pets considered, lobster pot, food processor, …
  • 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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$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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$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

Chilmark house
4 BR / 3 BA / Sleeps 8 | Quick view

Details

Ferry Tickets Available - Please Inquire Charming 4 bedroom, 3 bath traditional summer cottage. Enjoy this impeccably maintained summer home surrounded by a mature landscaped yard with lots of flowering shrubbery. A large deck offers privacy and a wonderful setting for those summer barbecues. A modern well equipped …
  • 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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$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

Chilmark house
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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$258

4 BR / 0 BA / Sleeps 9

1 / 8

$258

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#2007 Quintessential Chilmark farm house on 12 acre estate

Chilmark house
4 BR / Sleeps 9 | Quick view

Details

Quintessential Chilmark farm house on 12 acre estate. Renovated 1700's house offering antique qualities with the modern conveniences. Very private and tranquil. Enjoy the beautiful south shore Chilmark beaches with this rental. Additional amenities include: cleaning fee: $180, check in time: 4:00, security deposit: $…
  • Internet Access
  • Deck
  • Dishwasher
  • Microwave
  • Toaster
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$429

3 BR / 1 BA / Sleeps 6

1 / 16

$429

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Chilmark in the Woods (Chilmark-in-the-Woods-CH230)

Chilmark house
3 BR / 1 BA / Sleeps 6 | Quick view

Details

Newly renovated kitchen. Great yard and deck. Tucked into the woods off South Road. 1.3 miles from West Tisbury town center. Access to Lucy Vincent and Squibnocket Beaches. Convenient location in Chilmark. West Tisbury Farmer's Market & Artisan's Market are just down the road. Relax in the privacy of the back yard. …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$572

3 BR / 3 BA / Sleeps 8

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 / 0 BA / Sleeps 8

1 / 13

$286

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#2071 A very special Windy Gates offering

Chilmark house
4 BR / Sleeps 8 | Quick view

Details

A very special Windy Gates offering. Four bedroom converted barn offers a large open first floor with kitchen, dining and living space. Great barn doors open to patio seating outside. Four bedrooms upstairs with one hall bath and a second bath at the bottom of the stairs. Enjoy this Martha's Vineyard vacation rental …
  • Internet Access
  • Deck
  • Grill
  • Dishwasher
  • Microwave
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$315

4 BR / 3 BA / Sleeps 8

1 / 22

Details

This special summer retreat affords unforgettable views, a quiet and private setting, an awesome deck to sit and watch and let it all go. Newly renovated gourmet kitchen. The hgouse has views from every room. Watch the sailboat races on Menemsha Pond, the herons, the deer and the hawks on the marsh. Walk to the …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$150

4 BR / 2 BA / Sleeps 8

1 / 13

$150

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714 - SPACIOUS AND COMFORTABLE CHILMARK CAPE WITH CENTRAL AIR CONDITIONING

Chilmark house
4 BR / 2 BA / Sleeps 8 | Quick view

Details

This spacious and comfortably furnished contemporary Cape is conveniently located between Chilmark and West Tisbury. The master bedroom and bath are downstairs; three bedrooms and a bath are upstairs off the loft that overlooks the living and dining rooms. The living and dining rooms have a cathedral ceiling, wood …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Porch
  • Smoking allowed - ask
  • Suitable for children - over five
  • Suitable for the elderly - ask

PreviousNext property

$458

3 BR / 1 BA / Sleeps 6

1 / 19

Details

Rustic colorful camp with a gorgeous water view right on Chilmark Pond. Sleeps six. Simple kitchen with all necessities. Wow your guests with gourmet meals from this quaint kitchen. Comfortable living-dining overlooking the pond. A special get-away like old times. Not many of these left! Row or Kayak across the pond …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$150

4 BR / 0 BA / Sleeps 8

1 / 13

$150

Inquire

#2059 Access to Lucy Vincent & Squibnocket Beaches

Chilmark house
4 BR / Sleeps 8 | Quick view

Details

Four Bedroom Cape located in Chilmark on a circular drive. This Martha's Vineyard vacation rental offers private back yard with large deck for out door dining and sunning. Access to Lucy Vincent and Squibnocket Beaches just up the road. Additional amenities include: beach chairs, outdoor shower: enclosed, ipod dock, …
  • Internet Access
  • A/C or climate control
  • Deck
  • Dishwasher
  • Microwave
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$493

4 BR / 2 BA / Sleeps 8

1 / 15

$493

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Charming Chilmark Guest House (Charming-Chilmark-Guest-House-CH225)

Chilmark house
4 BR / 2 BA / Sleeps 8 | Quick view

Details

Perched high above the surrounding terrain, this affordable Chilmark rental offers sweeping views of the ocean and upisland all the way to Aquinnah. See the sunsets from the deck. It is spacious with 4 bedrooms to accommodate family and friends. See Chilmark rental #CH224 for family reunions or larger parties. Great …
  • Television
  • DVD Player
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$572

4 BR / 3 BA / Sleeps 8

1 / 22

$572

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HILLTOP HOUSE WITH DISTANT WATER VIEWS - CHIL AMOS-95

Chilmark house
4 BR / 3 BA / Sleeps 8 | Quick view

Details

Sitting high atop a ridge in Chilmark, the distant ocean views from Hilltop House stretch as far as Woods Hole and the Elizabeth Islands to Menemsha. The three-acre hillside setting is both spectacular and private. The recently renovated house has two walls of glass sliding doors that frame the Living Area and Kitchen…
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Porch
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • 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 -

Chilmark house
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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$571

3 BR / 2 BA / Sleeps 5

1 / 11

$571

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Fully booked for summer 2015

Chilmark cottage
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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$286

2 BR / 1 BA / Sleeps 4

1 / 19

$286

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MEADOW HOUSE ON BLUEBERRY RIDGE - CHIL VBAR-39GH

Chilmark house
2 BR / 1 BA / Sleeps 4 | Quick view

Details

Quietly tucked away in a pastoral setting on Blueberry Ridge, Meadow House features a modern interpretation of a sleek barn. The home is designed to enjoy the views of the surrounding secluded meadows both inside and out. The main living space features an open design floorplan with Living and Dining Areas accented by …
  • 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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$358

4 BR / 4 BA / Sleeps 8

1 / 21

$358

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

Chilmark house
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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$686

3 BR / 3 BA / Sleeps 6

1 / 16

$686

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746 - THE ESSENCE OF THE ISLAND WIITH ASSOCIATION BEACH

Chilmark house
3 BR / 3 BA / Sleeps 6 | Quick view

Details

Beautifully restored, maintained, and furnished, this 1740 Island farmhouse is situated on 80 private acres of glorious Chilmark hills overlooking Menemsha Pond and includes a small private association beach on Menemsha Pond to wend your way down to. A little bit of heaven on earth! Additional amenities include: …
  • 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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$429

4 BR / 3 BA / Sleeps 10

1 / 23

$429

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PINE RIDGE FARM: COUNTRY CAPE WITH GUEST COTTAGE - CHIL EHIN-05

Chilmark house
4 BR / 3 BA / Sleeps 10 | Quick view

Details

Pine Ridge Farm sits peacefully tucked away on three acres of gently rolling meadows surrounded by stone walls. At the center of the compound is a classic Royal Barry Wills cape that has been smartly designed and finely appointed. An open Great Room with Living and Dining Areas has a two-story vaulted ceiling and a …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Porch
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$858

6 BR / 4 BA / Sleeps 12

1 / 22

$858

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1148 - Chilmark Vacation Home with Lovely Views

Chilmark house
6 BR / 4 BA / Sleeps 12 | Quick view

Details

Historic 18th century New England home in a private landscaped setting on two and 1/2 acres with a waterview over Vineyard Sound and the Elizabeth Islands; a detached two-car garage, bunkhouse and tennis court located on Menemsha Inn Road in the Town of Chilmark. The dwelling is a charming and spacious Cape design, …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Wireless Internet
  • Fireplace
  • Washing Machine
  • Smoking allowed - ask
  • Suitable for children - over five
  • 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

Chilmark house
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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$486

4 BR / 3 BA / Sleeps 8

1 / 21

$486

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286 - CHARMING COUNTRY HOME IN CHILMARK

Chilmark house
4 BR / 3 BA / Sleeps 8 | Quick view

Details

Tastefully furnished and decorated with antiques and art. This upscale Chilmark summer home is an original Yankee Barn located off South Road that has all the accoutrements for summer entertaining. The post and beam structure features a beautiful cathedral living room brightened by southern light; has sliders out to a…
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Books
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - over five
  • Suitable for the elderly - ask

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$286

4 BR / 2 BA / Sleeps 8

1 / 8

$286

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1167 - CHARMING HOME W/VIEWS OF VINEYARD SOUND & ELIZABETH ISLANDS

Chilmark house
4 BR / 2 BA / Sleeps 8 | Quick view

Details

C-H-A-R-M-I-N-G is the only word to describe this privately set little contemporary with a big heart, tucked right into the woods in Spring Point. Lovely view of the Sound over the tree tops from the full length deck...dine inside comfort of screened-in porch. Convenient kitchen opens into living and dining area. …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Porch
  • Smoking allowed - ask
  • Suitable for children - over five
  • Suitable for the elderly - ask

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$358

2 BR / 1 BA / Sleeps 4

1 Reviews

$358

Inquire

THE BOATHOUSE ON STONEWALL POND - CHIL RALD-138B

Chilmark house
2 BR / 1 BA / Sleeps 4 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

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. The wraparound decks …
  • 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

Details

Reviews

(1)

spiritually reviving spot with mesmerising view

Left on Dec 27, 2013 for a stay in June 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 seen young ospreys learning how to fish (hilarious); sea otters eating their dinner right by the deck; busybody geese families; horseshoe crabs;a seal; deer and even a Labrador on a paddle board).

We have been coming …

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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

Chilmark house
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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$643

5 BR / 4 BA / Sleeps 9

6 Reviews

$643

Inquire

Stunning Multi-Generational 5 BR Ocean View Home!

Chilmark house
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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$345

3 BR / 3 BA / Sleeps 6

1 Reviews

$345

Book

Charming Chilmark 3 Bedroom 3 Bath Vacation Home

Chilmark house
3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Located in Chilmark on Martha's Vineyard, this 3 bedroom, 3 bathroom property is a perfect spring, summer or fall getaway. Cathedral ceilings create bright, airy spaces. Amenities include air conditioning, high speed internet, washer/dryer, gas fireplaces, TV in all rooms, outdoor shower, slate patio and beautifully …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Great house for the price

Left on Sep 12, 2013 for a stay in August 2013

This house is an unexpected surprise. it is very well equipped and was perfect for two couples for the week and a teenager who spent the weekend. Everyone had their privacy, and the house pulled us to congregate outside on the deck and patio overlooking a charming garden. For those who don't need excessive luxury, but want a pleasant setting that is easily accessible to up island and down, and …

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$286

4 BR / 5 BA / Sleeps 8

1 Reviews

$286

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653 - ATLANTIC OCEAN BREEZES,GLORIOUS VIEWS!

Chilmark house
4 BR / 5 BA / Sleeps 8 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

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 Squibnocket Peninsula, with…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - over five
  • Suitable for the elderly - ask

Details

Reviews

(1)

Fabulous stay

Left on Jun 16, 2014 for a stay in March 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 everyone loved being at this home and on the Vineyard for a winter vacation. The house is spacious, comfortable and very beautiful. The property is private.

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$3,000

5 BR / 4 BA / Sleeps 9

1 / 24

$3,000

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Exquisite Waterviews with Private Pool 116637

Chilmark house
5 BR / 4 BA / Sleeps 9 | Quick view

Details

Exclusive Chilmark retreat perfectly blends casual elegance with stunning waterviews and a private pool. Enjoy the ocean-facing deck which provides a front row seat with plenty of room for entertaining and outdoor dining. A truly magical mix of a spectacular waterfront location, situated atop a hill with private …
  • Shared outdoor pool (unheated)
  • 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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$572

4 BR / 3 BA / Sleeps 8

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$572

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1717 - Gracious and Spacious Chilmark Home with a Pool

Chilmark house
4 BR / 3 BA / Sleeps 8 | Quick view

Details

A perfect vacation house with miles of hiking trails and the best vineyard beach at your doorstep. Relax in the pool ~ it's heated! The "play" pool is 4 feet deep. Built with water therapy and children in mind; handicapped accessible. Total privacy, in one of the nicest parts of the island. The house has a flowing …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$1,072

4 BR / 4 BA / Sleeps 10

1 / 23

Details

This spacious ten room, architectural award winning design home is perched high on a hill with panoramic views of the Vineyard Sound and the Elizabeth Islands. There are five bedrooms, four and one half baths, a large deck for entertaining and watching the breathtaking sunsets, and three outdoor patios. There is a …
  • 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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$1,858

5 BR / 5 BA / Sleeps 10

1 / 27

$1,858

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Main & Guest House w/Quansoo Beach Access 114882

Chilmark house
5 BR / 5 BA / Sleeps 10 | Quick view

Details

Architect designed, beautifully appointed home and guest house on five acres in Chilmark. Knoll wooded lot on Tisbury Great Pond, fronted on large native grass meadow. This bright and airy home offers complete privacy and access to Quansoo beach. Kayakers will delight in exploring the Great Pond just outside the door…
  • Waterfront
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$929

4 BR / 0 BA / Sleeps 8

1 / 25

$929

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#2050 Private 7.2 acre compound with key to Quansoo Beach

Chilmark house
4 BR / Sleeps 8 | Quick view

Details

Located on 7.2 private acres in Chilmark, this 4500 sq. ft. home features a key to Quansoo beach, one of the most beautiful private association beaches on Martha's Vineyard Island. Professionally decorated with British West Indies style furnishings. Large gourmet kitchen includes a subzero refridgerator, wine chiller …
  • Internet Access
  • A/C or climate control
  • Deck
  • Dishwasher
  • Microwave
  • 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

Chilmark house
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

Chilmark house
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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$2,572

4 BR / 2 BA / Sleeps 7

1 / 24

$2,572

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Squibnocket Farm Beautiful Converted Barn 116303

Chilmark house
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

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$886

4 BR / 2 BA / Sleeps 6

1 / 9

$886

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PARKE - Magnificent Ocean Views, Private Association Beach Rights

Chilmark house
4 BR / 2 BA / Sleeps 6 | Quick view

Details

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 beach in Aquinnah …
  • Waterfront
  • Ocean or water views
  • Deck
  • Grill
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$408

5 BR / 2 BA / Sleeps 10

1 / 32

Details

Beautiful newly remodeled and newly furnished 4 bedroom home with private pool. Landscaping bordering the house and pool will be enhanced and ready for summer 2015, work to begin in April. Ten minute drive from the house to Menemsha village or Lucy Vincent beach. The house features a cook's kitchen with Silestone …
  • Internet Access
  • A/C or climate control
  • Patio
  • Grill
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$2,036

4 BR / 3 BA / Sleeps 8

1 / 22

$2,036

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1199 - Beautiful Main House and Barn with a Pool and views over a Pond

Chilmark house
4 BR / 3 BA / Sleeps 8 | Quick view

Details

A complete complex in a beautiful, peaceful setting: main house and barn with built-in pool, hottub, private tennis court and pond. One can walk to a lovely North Shore beach. This complex is surrounded by roses and perennials. Also, beach stickers for Lucy Vincent and Squibnocket are provided. Large kitchen supplied …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Washing Machine
  • Smoking allowed - ask
  • Suitable for children - over five
  • Suitable for the elderly - ask

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$486

4 BR / 2 BA / Sleeps 8

1 / 25

$486

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KOGAB - Chilmark, South Road, 3 Miles to Lucy Vincent Beach, WiFi

Chilmark house
4 BR / 2 BA / Sleeps 8 | Quick view

Details

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 sliders out to a wrap-…
  • Phone / Internet
  • Deck
  • Grill
  • Dishwasher
  • Microwave
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
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