Chilmark Vacation Rentals, Homes, & More

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Chilmark Massachusetts Vacation Rentals - Cottage
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: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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Chilmark Massachusetts Vacation Rentals - Home
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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Bedrooms:5
Bathrooms:5
Sleeps:10
Type:Home
Per night:$1,786 - $3,572
Per week:$12,500 - $25,000
Pets allowed:No
Internet:Yes

Newly constructed home has open concept living area with 270 degree water views, abundant natural sunlight, central AC, high end appliances, hardwood floors, rooftop deck with seating to view gorgeous island sunsets, access to several private beaches, and high speed internet...

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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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Exterior
1 / 11
Bedrooms:5
Bathrooms:3
Sleeps:12
Type:Home
Per night:$500 - $715
Per week:$3,500 - $5,000
Pets allowed:No
Internet:Yes

Spacious, well furnished and equipped, comfortable home in quiet neighborhood on 3 acres. Two master bedrooms, one on each floor; pool table. Within walking distance (about 1 mile) to small North Shore beach (Great Rock Bite). Three mile drive to Lucy Vincent Beach. Amenities ...

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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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Ocean Front, Private Beach
1 / 23

Chilmark Home
4 Bedrooms / 4 Bathrooms / Sleeps 8

from

$358

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
Per night:$358 - $3,572
Per week:$2,500 - $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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View of House
1 / 10

Chilmark Home
4 Bedrooms / 2 Bathrooms / Sleeps 8

“ 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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Pool Surrounded By Gardens
1 / 10

Chilmark Home
4 Bedrooms / 3 Bathrooms / 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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Yard, Deck and Waterview Side of House
1 / 31

Chilmark Home
5 Bedrooms / 4 Bathrooms / Sleeps 8

from

$736

/ night

Email Owner
Bedrooms:5
Bathrooms:4
Sleeps:8
Type:Home
Per night:$736 - $1,365
Per week:$5,150 - $9,550
Pets allowed:No
Internet:Yes

MVVR EXCLUSIVE: Spectacular 5 bedroom, 4. 5 bath retreat. Lovely distant waterviews overlooking the South Shore. Hilltop setting with privacy and a five minute drive to Lucy Vincent Beach. This spacious custom home has been decorated by one of the island's premier professionals. ...

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Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Home
Per night:$543 - $1,286
Per week:$3,800 - $9,000
Pets allowed:No
Internet:Yes

Owner Transfer Ferry Tickets - Please InquireStunning Waterfront Views. Kayak or swim across the pond to Stonewall Beach or just relax on the expansive decks overlooking the water. This is an immaculate older home, very comfortably furnished with 3 bedrooms and 2 baths. High Speed...

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Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$286 - $454
Per week:$2,000 - $3,175
Pets allowed:No
Internet:Yes

Charming recently renovated summer cottage features large open living room with sliders leading on to a screened porch and private deck beyond. Porch is fully furnished for dining and relaxing, providing aditional outdoor living space. The deck is private and surrounded by the yard...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 8

Chilmark Home
2 Bedrooms / 1 Bathroom / Sleeps 4

from

$358

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Home
Per night:$358 - $1,786
Per week:$2,500 - $12,500
Pets allowed:No
Internet:No

Main House on the same property may be occupied by Owner or another Tenant. Peaceful private setting on one of the most beautiful areas on the South Shore. Amenities and Features include... Waterfront Guest House, Private BeachAdditional amenities include: coffee maker, internet...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 21

Chilmark Home
5 Bedrooms / 4 Bathrooms / 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 adward 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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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 - $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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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:2
Bathrooms:1
Sleeps:4
Type:Home
Per night:$143 - $1,786
Per week:$1,000 - $12,500
Pets allowed:No
Internet:Yes

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....

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Bedrooms:3
Bathrooms:1
Sleeps:6
Type:Home
Per night:$458 - $543
Per week:$3,200 - $3,800
Pets allowed:No
Internet:Yes

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...

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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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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: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: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: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 / 23

Chilmark Home
6 Bedrooms / 4 Bathrooms / 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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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 / 33

Chilmark Home
4 Bedrooms / 2 Bathrooms / Sleeps 9

Bedrooms:4
Bathrooms:2
Sleeps:9
Type:Home
Per night:$1,429 - $2,858
Per week:$10,000 - $20,000
Pets allowed:No
Internet:No

Pristine renovated barn set on acres of extreme privacy with ocean views and private ocean beach. This is an extraordinary residence with exposed beams and glass walls framing expansive views of meadows and the Atlantic ocean beyond. The refined interior offers open living spaces,...

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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 / 6

Chilmark Home
4 Bedrooms / 2 Bathrooms / 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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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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Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$1,429 - $2,286
Per week:$10,000 - $16,000
Pets allowed:No
Internet:Yes

7 acre Luxury Chilmark Estate in an Idyllic setting of stone walls, perennial gardens and orchards. Private pool and hot tub surrounded by a large deck and bordered by tiered rose gardens. A regulation tennis court is set a short walk across the meadow. There is a beautiful natural...

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Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$425 - $540
Per week:$2,975 - $3,775
Pets allowed:No
Internet:Yes

Ferry Tickets available for weeks 7/4- 7/11, 7/11- 7/18, 7/18- 7/25 and 7/25- 8/1 - Please InquireCharming 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...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 25
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$400 - $543
Per week:$2,800 - $3,800
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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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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Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$379 - $422
Per week:$2,650 - $2,950
Pets allowed:No
Internet:Yes

Lovely 3 bedroom 2 bath home. All new kitchen and baths. Completely renovated - lots of glass for a light filled interior. This lovely home in a private setting is surrounded by mature Holly trees, Laurel and attractive native shrubs. 1 mile to Alley's General Store. 10 minute drive...

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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 / 9
Bedrooms:4
Bathrooms:2
Sleeps:6
Type:Home
Per night:$886
Per week:$6,200
Pets allowed:No
Internet:No

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...

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Chilmark Massachusetts Vacation Rentals - Home
1 / 22
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$572 - $786
Per week:$4,000 - $5,500
Pets allowed:No
Internet:Yes

Steps from Menemsha Pond – look across the ever- changing surface of the water to Menemsha, the Creek, the Lobsterville dunes, Vineyard Sound and the Elizabeth Islands. Magnificent sunsets from the living room. This cathedral- ceiling Modernist masterpiece is constructed entirely...

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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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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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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: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:$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: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:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$315 - $643
Per week:$2,200 - $4,500
Pets allowed:No
Internet:Yes

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 ...

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