Chilmark Vacation Rentals, Homes, & More

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1-50 of 89 Chilmark Rentals

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Secluded, end of the road location
1 / 8

Chilmark Home
2 Bedrooms / 1 Bathroom / Sleeps 8
Home / 2 Bedrooms / 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
Cottage / 3 Bedrooms / 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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Chilmark Massachusetts Vacation Rentals - Home
1 / 40

Chilmark Home
5 Bedrooms / 5 Bathrooms / Sleeps 10
Home / 5 Bedrooms / Sleeps 10

Bedrooms:5
Bathrooms:5
Sleeps:10
Type:Home
Per night:$1,472 - $3,572
Per week:$10,300 - $25,000
Pets allowed:No
Internet:Yes

Aptly named for its stunning perch in prestigious Squibnocket Farm on the shores of Squibnocket Pond, The Roost features panoramic water views that stretch from the far southwestern shoreline of Martha's Vineyard, across Chilmark's Squibnocket and Stonewall Beaches, and continue...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 4
Bedrooms:5
Bathrooms:5
Sleeps:10
Type:Home
Per night:$1,529 - $3,629
Per week:$10,700 - $25,400
Pets allowed:No
Internet:Yes

Dramatic ocean views, idyllic one of a kind location in gated community, private ocean beaches are but a few of the desirable features of this all new 5 bedroom, 5 bath contemporary home, set in one of the most Idyllic landscapes on Martha's Vineyard. Situated hilltop this gorgeous...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 38
Bedrooms:Studio
Bathrooms:3
Sleeps:10
Type:Home
Per night:$2,958 - $4,386
Per week:$20,700 - $30,700
Pets allowed:No
Internet:Yes

Expansive views of Chilmark Pond and the Atlantic Shoreline. Deeded access to pond, dock and private ocean beach (please inquire for more information). Newly completed 5400 square foot luxury home with ... multiple decks overlooks the masterfully landscaped grounds, stone walls,...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 16

Chilmark Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$322

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$322 - $1,179
Per week:$2,250 - $8,250
Pets allowed:No
Internet:No

Charming Chilmark cottage with panoramic South Shore waterviews. A five minute stroll to South surf beach. Private tennis courts shared with owners and other tenants. Access to Stonewall Pond for launching canoes and kayaks. Seaside cottage charm has been maintained throughout with...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 21

Chilmark Home
4 Bedrooms / 5 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

(1)“ Excellent ”1 Review

from

$357

/ night

Email Owner
Bedrooms:4
Bathrooms:5
Sleeps:8
Type:Home
Per night:$357 - $1,429
Per month:$10,710 - $42,870
Pets allowed:No
Internet:Yes

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,...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 16

Chilmark Home
3 Bedrooms / 3 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$686

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$686
Per month:$20,580
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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Chilmark Massachusetts Vacation Rentals - Home
1 / 13

Chilmark Home
5 Bedrooms / 6 Bathrooms / Sleeps 10
Home / 5 Bedrooms / Sleeps 10

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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Chilmark Massachusetts Vacation Rentals - Home
1 / 17

Chilmark Home
6 Bedrooms / 5 Bathrooms / Sleeps 10
Home / 6 Bedrooms / Sleeps 10

Bedrooms:6
Bathrooms:5
Sleeps:10
Type:Home
Per night:$1,071 - $1,143
Per month:$32,130 - $34,290
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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Chilmark Massachusetts Vacation Rentals - Home
1 / 8

Chilmark Home
4 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$643

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$643 - $786
Per month:$19,290 - $23,580
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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Chilmark Massachusetts Vacation Rentals - Home
1 / 24

Chilmark Home
4 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$2,036
Per month:$61,080
Pets allowed:No
Internet:No

A complete complex in a beautiful, peaceful setting: main house and barn with built- in pool, hot tub, 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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Chilmark Massachusetts Vacation Rentals - Home
1 / 18

Chilmark Home
4 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$643

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$643 - $714
Per month:$19,290 - $21,420
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 / 13

Chilmark Home
5 Bedrooms / 4 Bathrooms / Sleeps 8
Home / 5 Bedrooms / Sleeps 8

Bedrooms:5
Bathrooms:4
Sleeps:8
Type:Home
Per night:$2,215
Per week:$15,500
Pets allowed:No
Internet:Yes

Located in a tranquil setting overlooking Chilmark Pond off of South Road this is a magical summer vacation spot. Additional amenities include: coffee maker, outdoor shower, lobster pot, food processor, cd player, wine glasses, washer & dryer, ironing board....

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Chilmark Massachusetts Vacation Rentals - Home
1 / 23

Chilmark Home
6 Bedrooms / 4 Bathrooms / Sleeps 10
Home / 6 Bedrooms / Sleeps 10

Bedrooms:6
Bathrooms:4
Sleeps:10
Type:Home
Per night:$1,215 - $1,500
Per week:$8,500 - $10,500
Pets allowed:No
Internet:Yes

Contemporary Home commands one of Martha's Vineyard's most spectacular views overlooking the Elizabeth Islands and Vineyard Sound. Breathtaking sunsets. Outdoor patios and deck and multiple living areas provide many options for family gatherings or quiet times. Amenities and Features...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 24
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$1,029 - $1,343
Per week:$7,200 - $9,400
Pets allowed:No
Internet:Yes

Outstanding private rental home nestled on 7. 2 private acres in the seaside community of Chilmark on the Island of Martha's Vineyard, features a key to Quansoo Beach, one of the most beautiful private association beaches on the island. Warmth, comfort and charm await you and your...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 20

Chilmark Home
6 Bedrooms / 4 Bathrooms / Sleeps 12
Home / 6 Bedrooms / Sleeps 12

from

$857

/ night

Email Owner
Bedrooms:6
Bathrooms:4
Sleeps:12
Type:Home
Per night:$857
Per month:$25,710
Pets allowed:No
Internet:Yes

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; tennis court and in- ground heated lap pool located on Menemsha Inn Road in the Town...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 10

Chilmark Home
4 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

(1)“ Excellent ”1 Review

from

$593

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$593
Per week:$4,150
Pets allowed:No
Internet:Yes

Owner Transfer Ferry Tickets - Please InquireSituated on a cul- de- sac overlooking a private meadow with spreading oaks ensures privacy. The screened porch, meadow bench, hammock and second floor deck off the master bedroom provide quiet spots to get away. Amenities and Features...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 11

Chilmark Home
4 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$150

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$150 - $429
Per month:$4,500 - $12,870
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 / 25

Chilmark Home
4 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$486

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$486 - $579
Per week:$3,400 - $4,050
Pets allowed:No
Internet:Yes

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...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 6

Chilmark Home
4 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$693

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$693 - $979
Per week:$4,850 - $6,850
Pets allowed:No
Internet:Yes

Enjoy the in ground pool and spectacular ocean views from this casual, mostly glass hill top contemporary. Kick back and relax by the pool in an area of splendid nature. Amenities and Features include... Spectacular Waterviews, Pool, WiFiAdditional amenities include: coffee maker,...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 10

Chilmark Home
4 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$1,215
Per week:$8,500
Pets allowed:No
Internet:No

High in the hills of peaceful Chilmark with distant panoramic waterviews, this four bedroom impeccably maintained house with in gound pool is surrounded by beautifully landscaped grounds. Expansive decks invite you to make the most of summer living. Amenities and Features include......

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Chilmark Massachusetts Vacation Rentals - Home
1 / 23

Chilmark Home
4 Bedrooms / 4 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$500

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
Per night:$500 - $3,572
Per week:$3,500 - $25,000
Pets allowed:No
Internet:Yes

Ocean Front Splendor in an elegant and comfortable beach house. Sunrise from the ocean, sunset over the adjoining 13- acre Sheriff's Meadow Foundation conservation preserve. Walk to your private beach. New 500 square foot addition, added for summer 2008, includes ground floor Master...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 14

Chilmark Home
5 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 5 Bedrooms / Sleeps 8

from

$390

/ night

Email Owner
Bedrooms:5
Bathrooms:3
Sleeps:8
Type:Home
Per night:$390 - $1,104
Per week:$2,725 - $7,725
Pets allowed:No
Internet:Yes

Classic coastal cottage remodeled in 2000. Charming open and sunny interior feautres 3 bedrooms and 2 baths in the main house. 2nd level Master bedroom opens onto private deck with views of Menemsha Harbor. Seperate guest cottage has Qeen bedroom and a full bath. Outdoor spaces for...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 15

Chilmark Home
4 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$1,357
Per month:$40,710
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 / 28

Chilmark Home
4 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$358

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$358 - $572
Per week:$2,500 - $4,000
Pets allowed:No
Internet:Yes

CHILMARK, Black Point Beach HeavenSand Sun Surf and an immaculate house and guest quarters too................ WOWThis is not a fancy posh beach house. It is a wonderful relaxing, immaculate vacation destination for you and your family. You will find peace, ocean breezes, the ...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 29

Chilmark Home
6 Bedrooms / 2 Bathrooms / Sleeps 11
Home / 6 Bedrooms / Sleeps 11

from

$858

/ night

Email Owner
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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Chilmark Massachusetts Vacation Rentals - Home
1 / 15

Chilmark Home
5 Bedrooms / 4 Bathrooms / Sleeps 10
Home / 5 Bedrooms / Sleeps 10

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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Chilmark Massachusetts Vacation Rentals - Home
1 / 23
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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Chilmark Massachusetts Vacation Rentals - Home
1 / 23

Chilmark Home
4 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

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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Chilmark Massachusetts Vacation Rentals - Home
1 / 28

Chilmark Home
6 Bedrooms / 6 Bathrooms / Sleeps 12
Home / 6 Bedrooms / Sleeps 12

Bedrooms:6
Bathrooms:6
Sleeps:12
Type:Home
Per night:$2,858 - $4,286
Per week:$20,000 - $30,000
Pets allowed:No
Internet:Yes

Vista Point combines a truly magical mix of a spectacular, waterfront location, with equaling stunning architectural design. Sitting high atop a north shore ridge in Chilmark, the views stretch west from the Aquinnah cliffs and lighthouse, north to the Elizabeth Islands, and ...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 29

Chilmark Home
5 Bedrooms / 5 Bathrooms / Sleeps 10
Home / 5 Bedrooms / Sleeps 10

Bedrooms:5
Bathrooms:5
Sleeps:10
Type:Home
Per night:$1,786 - $2,358
Per week:$12,500 - $16,500
Pets allowed:No
Internet:Yes

Tucked away in the prestigious Quansoo area of Chilmark, this architect- designed compound sits peacefully on the shores of the Tisbury Great Pond. There are sophisticated touches inside and out, with a Main House, Guest House, and key access to Quansoo Beach. The Main House is...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 31

Chilmark Home
7 Bedrooms / 4 Bathrooms / Sleeps 9
Home / 7 Bedrooms / Sleeps 9

Bedrooms:7
Bathrooms:4
Sleeps:9
Type:Home
Per night:$1,786 - $3,572
Per week:$12,500 - $25,000
Pets allowed:No
Internet:Yes

Serenely tucked away on the rolling hills and meadows of prestigious Seven Gates Farm, this Classic Chilmark home sits directly on the north shore with stunning water views of Vineyard Sound and the Elizabeth Islands, with its own curving coastline of Seven Gates beach. There is...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 36

Chilmark Home
4 Bedrooms / 5 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$358

/ night

Email Owner
Bedrooms:4
Bathrooms:5
Sleeps:8
Type:Home
Per night:$358 - $3,572
Per week:$2,500 - $25,000
Pets allowed:No
Internet:Yes

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...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 23

Chilmark Home
3 Bedrooms / 3 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$786

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$786 - $1,215
Per week:$5,500 - $8,500
Pets allowed:No
Internet:Yes

This historic farmhouse is quietly tucked away above Menemsha Pond with sweeping sunset and water views of The Pond and Menemsha Harbor. The tranquil setting is classic Chilmark with rolling hills and stonewalls, plus a private association beach just a short stroll away on Menemsha...

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Bedrooms:5
Bathrooms:2
Sleeps:10
Type:Home
Per night:$408 - $1,122
Per week:$2,850 - $7,850
Pets allowed:No
Internet:Yes

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...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 18

Chilmark Home
3 Bedrooms / 3 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$383

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$383 - $512
Per week:$2,680 - $3,580
Pets allowed:No
Internet:Yes

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...

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Bedrooms:4
Bathrooms:3
Sleeps:6
Type:Home
Per night:$543 - $1,186
Per week:$3,800 - $8,300
Pets allowed:No
Internet:Yes

This incredible home is furnished with one of a kind artisan wood and textile pieces, as well as Donghia soft seating and is filled with art, vintage stain glass, antiques, and one of kind artisan furniture. The ocean view is spectacular from the great room (living room, dining...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 14

Chilmark Home
1 Bedroom / 2 Bathrooms / Sleeps 3
Home / 1 Bedroom / Sleeps 3

from

$736

/ night

Email Owner
Bedrooms:1
Bathrooms:2
Sleeps:3
Type:Home
Per night:$736
Per week:$5,150
Pets allowed:No
Internet:No

"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...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 21

Chilmark Home
4 Bedrooms / 4 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$358

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
Per night:$358 - $929
Per week:$2,500 - $6,500
Pets allowed:No
Internet:Yes

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 ...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 29

Chilmark Home
5 Bedrooms / 5 Bathrooms / Sleeps 10
Home / 5 Bedrooms / Sleeps 10

Bedrooms:5
Bathrooms:5
Sleeps:10
Type:Home
Per night:$1,472 - $3,572
Per week:$10,300 - $25,000
Pets allowed:No
Internet:Yes

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 ...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 25

Chilmark Home
3 Bedrooms / 3 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$500

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$500 - $622
Per week:$3,500 - $4,350
Pets allowed:No
Internet:Yes

A quiet oasis tucked away on Blueberry Ridge, the Hillside Hideaway enjoys a tranquil country setting with rolling meadows, and thoughtfully designed outdoor landscaping with patios and outdoor living spaces set amid nicely manicured grounds and gardens. Inside, the house is designed...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 18

Chilmark Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$643

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$643 - $858
Per week:$4,500 - $6,000
Pets allowed:No
Internet:No

Amenities and Features include... Quansoo (with private beach key), Central Air, Waterview, WaterfrontAdditional amenities include: coffee maker, internet - ethernet cord required, pets considered, lobster pot, washer / dryer, cd player, porch - screened, outside shower...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 15

Chilmark Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$279

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$279 - $408
Per week:$1,950 - $2,850
Pets allowed:No
Internet:Yes

Amenities and Features include... A/C, WiFiAdditional 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....

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Chilmark Massachusetts Vacation Rentals - Home
1 / 18

Chilmark Home
5 Bedrooms / 2 Bathrooms / Sleeps 9
Home / 5 Bedrooms / Sleeps 9

from

$429

/ night

Email Owner
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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Chilmark Massachusetts Vacation Rentals - Home
1 / 24

Chilmark Home
4 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 4 Bedrooms / Sleeps 6

from

$454

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:6
Type:Home
Per night:$454 - $597
Per week:$3,175 - $4,175
Pets allowed:No
Internet:Yes

Casual immaculately clean in picturesque Menemsha, Chilmark waterfront. Beautiful views. A short stroll to the beach, fish market, boutiques, fishing, and shore dinners. Guest House - Main House on property nearby may be occupied by Tenants or Owner. Amenities and Features include......

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Chilmark Massachusetts Vacation Rentals - Home
1 / 20

Chilmark Home
3 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

from

$572

/ night

Email Owner
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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Chilmark Massachusetts Vacation Rentals - Home
1 / 35

Chilmark Home
3 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

from

$500

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Home
Per night:$500 - $1,243
Per week:$3,500 - $8,700
Pets allowed:No
Internet:Yes

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....

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Chilmark Massachusetts Vacation Rentals - Home
1 / 8

Chilmark Home
4 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$286

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$286 - $594
Per month:$8,580 - $17,820
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 inside comfort of screened- in porch. Convenient kitchen opens...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 21

Chilmark Home
5 Bedrooms / 4 Bathrooms / Sleeps 12
Home / 5 Bedrooms / Sleeps 12

from

$400

/ night

Email Owner
Bedrooms:5
Bathrooms:4
Sleeps:12
Type:Home
Per night:$400 - $829
Per week:$2,800 - $5,800
Pets allowed:No
Internet:Yes

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......

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