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264 Houses

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Chilmark Farmhouse with access to Hancock Beach

Chilmark house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

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$715

Striking 5BR/4BA Chilmark Contemporary with Views of the Sound

Chilmark house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

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$900

Gracious and Spacious Chilmark Home with a Pool

Chilmark house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$686

CHARMING COUNTRY HOME IN CHILMARK

Chilmark house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$500

Great rentals within 20 miles that match your search

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$783

AMAZING BEACH COTTAGE AVAILABLE AUG 5 -12

Westport Point house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 17 minutes

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$541

Contemporary 4 Bedroom House One Mile to Beach

New Seabury house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

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$831

Vineyard Haven Guest House - Sleeps 4, A/C, Walk to Town

Vineyard Haven house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“great stay in Vineyard Haven” We enjoyed staying in David's guest house. It was clean, well situated (a short walk from downtown Vineyard Haven), and made for a relaxing few days on the Vineyard. David was easy to reach and very responsive to any of our needs. I would highly recommend you stay at the guesthouse.

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$264

Charming 3br Getaway in Oak Bluffs

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$345

Waterfront Resort in Falmouth - 5/31/24 - 6/7/24

Falmouth apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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$172

Katama House "CLOSE TO THE BEACH"

Acushnet house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$311

“A thoroughly enjoyably experience!” Dave was wonderful to work with and offered advise on where some of the best areas to kayak might be found... saw several ospreys and other wildlife. The cottage has all new appliances and was clean. Sitting on the waterfront in the morning with coffee and the afternoon with a toddy was a great way to start and end each day.

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Price per night from

$345

Falmouth Heights steps to Beaches...Clean and Comfortable

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$574

Oak Bluffs Contemporary Summer Home

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$361

Walk to Beach from 4 Bedroom Falmouth Village Home

Falmouth house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$517

Cape Cod -Falmouth - Beachfront Olde Cape Cod Charm

Falmouth house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 9

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$501

Great Location, Beautiful Home

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$738

Ocean, lake, harbor & parkview Vineyard cottage w/AC and auto ferry tics

Oak Bluffs cottage

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 10

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$1,148

New Cape House Steps to the Beach in East Falmouth

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$431

Magnificent Contemporary on Exclusive Point

Falmouth house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

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$918

Charming Lambert's Cove Beach House

West Tisbury house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$431

Sweet Cottage in Woods Hole Village Steps to Beach

Woods Hole cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

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$431

Seaside cottage

Falmouth cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$493

Charming 4 bedroom home in the east chop neighborhood of Oak Bluffs

Oak Bluffs house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$574

2+BR Renovated Gingerbread Cottage - Walk to All

Oak Bluffs house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

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$525

Edgartown - Clean, quiet, and comfortable home close to bike trail

Edgartown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$746

Spectacular Martha's Vineyard Island Home!

Oak Bluffs townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 16 minutes

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$454

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$1,090

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$746

Walk to Private Beach

Falmouth studio

  • Studio
  • 1 bathroom
  • sleeps 4

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Price per night from

$156

Salt Water Front South of Rt. 28 with Private Dock and Amazing Views!

Teaticket house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$660

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$3,843

Vineyard Charming Retreat near beaches and center

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 3 hours 15 minutes

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Price per night from

$402

Walk to the Beach! NEW Hot Tub! Pets welcome!

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$388

Renovated Cottage near center and beaches

Edgartown house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 3 hours 15 minutes

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Price per night from

$803

Heated Pool, AC, WiFi, Sleeps 18, 2 mi to beach!

Oak Bluffs house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 19

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$6,883

GREAT VACATION HOUSE-GREAT LOCATION TO SOUTH BEACH

Edgartown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$345

Vineyard House - South Beach Down The Street

Edgartown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$345

Viewing 38 of 264
rentals in Chilmark

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