Chilmark Vacation Rentals, Homes, & More

1-50 of 172 Chilmark Rentals

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Secluded, end of the road location
1 / 8

Chilmark Home
2 Bedrooms / 1 Bathroom / Sleeps 8

from

$79

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:8
Type:Home
Per night:$79 - $229
Per week:$550 - $1,600
Pets allowed:No
Internet:No

Located at end of a dead- end dirt road on 1. 5 acres with tall pines and oaks. Modified saltbox, owner designed & built in 1978 for potential active solar. First floor has a large country kitchen, living room, bathroom with antique claw foot bathtub & w/d, & 2 decks. Second floor...

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1 / 11

Chilmark Cottage
3 Bedrooms / 2 Bathrooms / Sleeps 5

from

$572

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:5
Type:Cottage
Per night:$572
Per week:$4,000
Pets allowed:Yes
Internet:Yes

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...

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Bedrooms:6
Bathrooms:2
Sleeps:14
Type:Home
Per night:$475 - $550
Per week:$3,325 - $3,850
Pets allowed:No
Internet:Yes

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...

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1 / 13

Chilmark Home
3 Bedrooms / 1 Bathroom / Sleeps 6

from

$429

/ night

Email Owner
Bedrooms:3
Bathrooms:1
Sleeps:6
Type:Home
Per night:$429
Per week:$3,000
Pets allowed:No
Internet:Yes

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...

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Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$286 - $500
Per week:$2,000 - $3,500
Pets allowed:No
Internet:No

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-...

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Bedrooms:6
Bathrooms:2
Sleeps:11
Type:Home
Per night:$858 - $1,429
Per week:$6,000 - $10,000
Pets allowed:No
Internet:Yes

Style, warmth, and comfort define this delightful farm house in Menemsha with a water view to theVineyard Sound. The property is spacious and private. There is a tennis court shared by the occupants of the neighboring barn. The house comes with a key to a beach in Aquinnah on Moshup...

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Bedrooms:4
Bathrooms:4
Sleeps:10
Type:Home
Per night:$1,072 - $1,429
Per week:$7,500 - $10,000
Pets allowed:No
Internet:Yes

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,...

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Bedrooms:5
Bathrooms:4
Sleeps:10
Type:Home
Per night:$1,572 - $2,143
Per week:$11,000 - $15,000
Pets allowed:No
Internet:Yes

Contemporary, private, exquisite home set right on Tisbury Great Pond. Drive to Quansoo or kayak right from the house. Large, gorgeous gourmet kitchen, spacious living room with stylish fire place, large screened porch, water views through the trees all contribute to the heightened...

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Bedrooms:5
Bathrooms:3
Sleeps:10
Type:Home
Per night:$786
Per week:$5,500
Pets allowed:No
Internet:Yes

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...

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Bedrooms:5
Bathrooms:2
Sleeps:9
Type:Home
Per night:$715 - $1,286
Per week:$5,000 - $9,000
Pets allowed:Yes
Internet:Yes

Sweeping views of Squibnocket Pond, Dunes, the South Shore, Nomans Land, to sunsets over Aquinnah. A great family getaway with access to Chilmark's famed Lucy Vincent and Squibnocket Beaches as well as a private association beach in Aquinnah. Roomy and inviting, this house offers...

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Bedrooms:5
Bathrooms:2
Sleeps:9
Type:Home
Per night:$429 - $643
Per week:$3,000 - $4,500
Pets allowed:No
Internet:Yes

Reverse Contemporary Five Bedroom home just minutes to Menemsha. There are open living spaces with living room , dining room and kitchen that open to deck with waterviews of the North Shore. Just a short drive to famous Lucy Vincent Beach, Chilmark Store, library and Community ...

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Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$1,143 - $1,286
Per week:$8,000 - $9,000
Pets allowed:No
Internet:Yes

Panoramic Views of South Shore from across the Allen Farm to Noman's Land and beyond. This carefully designed and decorated home sets you in beauty and comfort. The deck features a gazebo. The yard is carefully landscaped and tended with trees strategically planted to offer privacy...

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Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$493 - $565
Per week:$3,450 - $3,950
Pets allowed:No
Internet:No

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...

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Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Home
Per night:$572 - $858
Per week:$4,000 - $6,000
Pets allowed:No
Internet:Yes

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, ...

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Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$1,072
Per week:$7,500
Pets allowed:No
Internet:Yes

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 ...

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Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$893 - $1,108
Per week:$6,250 - $7,750
Pets allowed:No
Internet:Yes

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...

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Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$358 - $1,072
Per week:$2,500 - $7,500
Pets allowed:No
Internet:Yes

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...

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Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$686
Per week:$4,800
Pets allowed:No
Internet:No

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....

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Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$386 - $397
Per week:$2,700 - $2,775
Pets allowed:No
Internet:Yes

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...

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Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$358 - $386
Per week:$2,500 - $2,700
Pets allowed:No
Internet:Yes

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 ...

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Bedrooms:4
Bathrooms:2
Sleeps:2
Type:Home
Per night:$1,143 - $1,215
Per week:$8,000 - $8,500
Pets allowed:No
Internet:Yes

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...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 13

Chilmark Home
6 Bedrooms / 0 Bathroom / Sleeps 14

from

$500

/ night

Email Owner
Bedrooms:6
Sleeps:14
Type:Home
Per night:$500 - $929
Per week:$3,500 - $6,500
Pets allowed:No
Internet:Yes

Spectacular views from this updated 18th century traditional home in Chilmark. Great master suite, family room and deck. Mooring available. Access to small beach area just down the path to Clam Point Cove. Ideal Martha's Vineyard vacation rental for clamming, kayaking and sailing....

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Chilmark Massachusetts Vacation Rentals - Home
1 / 15
Bedrooms:6
Sleeps:12
Type:Home
Per night:$2,858 - $4,286
Per week:$20,000 - $30,000
Pets allowed:No
Internet:Yes

Stunning Chilmark rental home. This newly constructed contemporary home is situated high up from the water with fabulous views of the North Shore. There are numerous paths great for a hike or a run in the woods. Privacy, privacy, privacy. Great space in the main house with five ...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 7

Chilmark Home
5 Bedrooms / 0 Bathroom / Sleeps 10

Bedrooms:5
Sleeps:10
Type:Home
Per night:$2,858
Per week:$20,000
Pets allowed:No
Internet:Yes

Spectacular contemporary Martha's Vineyard vacation rental offering 5, 000 square feet of casually elegant living space. Overlooking Chilmark pond and Lucy Vincent Beach with professionally landscaped grounds. Enjoy lounging on the deck with an in- ground negative edge swimming pool....

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Chilmark Massachusetts Vacation Rentals - Home
1 / 15
Bedrooms:5
Sleeps:10
Type:Home
Per night:$929 - $2,358
Per week:$6,500 - $16,500
Pets allowed:No
Internet:Yes

Vacation in Chilmark on the pristine shores of the Tisbury Great Pond in this custom contemporary built with only the best materials. Four- bedroom main house with a detached guest suite. Open living/Dining/kitchen area with cathedral ceilings and exposed beams overlooking a luxurious...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 14
Bedrooms:5
Sleeps:10
Type:Home
Per night:$572 - $1,143
Per week:$4,000 - $8,000
Pets allowed:No
Internet:Yes

Stunning Chilmark rental property with beautiful views to the south across Squibnocket Pond and the Atlantic and to the north across Menemsha Pond to the Elizabeth Islands. The house was built in the 1950s in a manner to maximize the enjoyment of the wonderful setting and views. It...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 9

Chilmark Home
4 Bedrooms / 0 Bathroom / Sleeps 9

from

$786

/ night

Email Owner
Bedrooms:4
Sleeps:9
Type:Home
Per night:$786 - $1,215
Per week:$5,500 - $8,500
Pets allowed:No
Internet:Yes

Lovely, Chilmark home in close proximity to Menemsha House offers four bedrooms with comfortable kitchen, living and dining area. Great deck off back of house with views of Vineyard Sound. Very relaxing Martha's Vineyard vacation rental. Additional amenities include: longitude: ...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 19
Bedrooms:4
Sleeps:9
Type:Home
Per night:$1,429 - $2,858
Per week:$10,000 - $20,000
Pets allowed:No
Internet:Yes

Stunning Chilmark property with wonderful privacy, peace and tranquility. This Martha's Vineyard vacation rental offers access to two keyed private association beaches Squibnocket Association and Long Beach, distant peak of a view to the Atlantic Ocean with classic Chilmark living...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 15
Bedrooms:5
Sleeps:9
Type:Home
Per night:$1,429 - $2,858
Per week:$10,000 - $20,000
Pets allowed:No
Internet:Yes

A rare Chilmark find! This house sits up on a bluff with the most spectacular Atlantic views over Squibnocket Beach. There are two paths down to the beach as well as keys to two of the most pristine island beaches within the gated association. The Bluff house blends the traditional...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 13

Chilmark Home
4 Bedrooms / 0 Bathroom / Sleeps 8

from

$429

/ night

Email Owner
Bedrooms:4
Sleeps:8
Type:Home
Per night:$429 - $786
Per week:$3,000 - $5,500
Pets allowed:No
Internet:Yes

Lovely four bedroom home in Menemsha Hills, Chilmark. House offers distant views from upper level over Menemsha on one side and across to Vineyard Sound on the other. Nicely appointed furnishings. The house has a patio off the dining room and kitchen overlooking grounds and gardens....

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Chilmark Massachusetts Vacation Rentals - Home
1 / 17

Chilmark Home
3 Bedrooms / 0 Bathroom / Sleeps 8

from

$786

/ night

Email Owner
Bedrooms:3
Sleeps:8
Type:Home
Per night:$786
Per week:$5,500
Pets allowed:No
Internet:Yes

This Chilmark rental home is well equipped for the family – Featuring central a/c, surround sound stereo, private baths for all 3 bedrooms, huge kitchen with island seating as well as open dining room with wine cooler, this vacation rental provides privacy as well as ample living...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 18

Chilmark Home
4 Bedrooms / 0 Bathroom / Sleeps 7

from

$929

/ night

Email Owner
Bedrooms:4
Sleeps:7
Type:Home
Per night:$929
Per week:$6,500
Pets allowed:No
Internet:Yes

Wonderful cape style house up on the hill in Abel's Hill. This sprawling house offers great space and is perfect for entertaining. Large deck off of the back offer lovely field views. Enjoy lovely summer evenings under the stars next to the fire pit. Association access to tennis and...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 10
Bedrooms:4
Sleeps:6
Type:Home
Per night:$858 - $929
Per week:$6,000 - $6,500
Pets allowed:No
Internet:Yes

Wonderful, vintage Martha's Vineyard cottage. Simple living in Chilmark with modern conveniences. House offers four bedrooms with wonderful views over rolling meadow to Squibnocket Pond and Atlantic Ocean. Access to key beach in Gay Head. Additional amenities include: dock/boat- ...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 22

Chilmark Home
6 Bedrooms / 4 Bathrooms / Sleeps 12

from

$858

/ night

Email Owner
Bedrooms:6
Bathrooms:4
Sleeps:12
Type:Home
Per night:$858 - $1,429
Per week:$6,000 - $10,000
Pets allowed:No
Internet:No

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...

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Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$286 - $715
Per week:$2,000 - $5,000
Pets allowed:No
Internet:Yes

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...

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Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$643 - $929
Per week:$4,500 - $6,500
Pets allowed:No
Internet:Yes

A fascinating, lovely classic Eliot Noyes (architect) contemporary in a private setting with spectacular views off the water looking toward Lucy Vincent beach and East towards West Tisbury. There is a great room (with dining, and living room and kitchen) with decks on either side...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 21

Chilmark Home
4 Bedrooms / 3 Bathrooms / Sleeps 8

from

$486

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$486 - $543
Per week:$3,400 - $3,800
Pets allowed:Yes
Internet:Yes

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...

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Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$179 - $429
Per week:$1,250 - $3,000
Pets allowed:No
Internet:Yes

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...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 16

Chilmark Home
3 Bedrooms / 3 Bathrooms / Sleeps 6

from

$858

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$858 - $1,358
Per week:$6,000 - $9,500
Pets allowed:No
Internet:Yes

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!...

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Bedrooms:5
Bathrooms:6
Sleeps:10
Type:Home
Per night:$2,000 - $2,358
Per week:$14,000 - $16,500
Pets allowed:No
Internet:Yes

Vacation in Chilmark near the pristine shores of the Tisbury Great Pond in this brand new, custom contemporary built with only the best materials. Four- bedroom main house with a detached guest suite. Open living / dining/ kitchen area with cathedral ceilings and exposed beams overlooking...

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Bedrooms:6
Bathrooms:5
Sleeps:10
Type:Home
Per night:$1,072 - $1,429
Per week:$7,500 - $10,000
Pets allowed:No
Internet:Yes

Spacious, 10 room, architectual award- winning design home perched atop a hill w/panoramic view of Vineyard Sound and the Elizabeth Islands. The large deck has marvelous water views and the sunsets are spectacular! Its charming interior includes a Living Room with vaulted ceilings,...

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Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$2,036 - $2,286
Per week:$14,250 - $16,000
Pets allowed:No
Internet:Yes

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...

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Bedrooms:5
Bathrooms:4
Sleeps:8
Type:Home
Per night:$1,929 - $2,072
Per week:$13,500 - $14,500
Pets allowed:No
Internet:No

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 ...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 8

Chilmark Home
4 Bedrooms / 3 Bathrooms / Sleeps 8

from

$786

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$786 - $1,072
Per week:$5,500 - $7,500
Pets allowed:No
Internet:Yes

Unique combination of 1940's camp- style home and new (2007) two- story addition. Beautiful Ocean views from all floors, two decks, two living rooms and wonderful prevailing SW breezes. Five minute walk to Ocean Beach adjacent to Lucy Vincent Beach. Access to private Able's Hill...

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Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$1,358
Per week:$9,500
Pets allowed:No
Internet:Yes

Beautiful, custom 4- bedroom house in an exclusive neighborhood with private association beach and tennis court. Spacious, comfortable living and dining room with cathedral ceilings, open to kitchen and upstairs loft with office. TV/sitting room nook off dining room. Expansive ...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 8
Bedrooms:4
Sleeps:9
Type:Home
Per night:$258 - $586
Per week:$1,800 - $4,100
Pets allowed:No
Internet:Yes

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...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 26
Bedrooms:4
Sleeps:10
Type:Home
Per night:$1,143 - $1,429
Per week:$8,000 - $10,000
Pets allowed:No
Internet:Yes

Spectacular waterviews! This Martha's Vineyard vacation rental is situated on 3+ acres overlooking the Elizabeth Islands and the Vineyard sound. On a clear day you can catch a lovely view of the Aquinnah lighthouse. The outdoor living space is truly where you want to be. Each area...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 17

Chilmark Home
5 Bedrooms / 0 Bathroom / Sleeps 10

from

$358

/ night

Email Owner
Bedrooms:5
Sleeps:10
Type:Home
Per night:$358 - $986
Per week:$2,500 - $6,900
Pets allowed:No
Internet:Yes

A grand summer house on Martha's Vineyard where memories are made. This landmark, hilltop Victorian offers magnificent 270- degree views over meadows, Menemsha Pond and the North shore. Access to Hancock Beach with adjacent parking, as well as Menemsha pond within walking distance....

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Chilmark Massachusetts Vacation Rentals - Home
1 / 19

Chilmark Home
4 Bedrooms / 0 Bathroom / Sleeps 10

from

$429

/ night

Email Owner
Bedrooms:4
Sleeps:10
Type:Home
Per night:$429 - $929
Per week:$3,000 - $6,500
Pets allowed:No
Internet:Yes

Elegant Architectural Digest Cape home in Chilmark, in pristine condition. Many fine details to this Martha's Vineyard vacation home. Custom woodwork, antique heart pine floors and fireplaces. Luxury construction (as compared to custom) built in 1998. Custom cabinetry with gourmet...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 21

Chilmark Home
5 Bedrooms / 0 Bathroom / Sleeps 10

Bedrooms:5
Sleeps:10
Type:Home
Per night:$1,429
Per week:$10,000
Pets allowed:No
Internet:Yes

This sprawling farm house which neighbors the Blue Heron Farm in Chilmark is a found jewel with fabulous views. The property offers five beautifully decorated bedrooms each with their own vineyard charm. Four being in the main house and a bunk room perfect for kids over the garage....

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