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268 Houses

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Chilmark Farmhouse with access to Hancock Beach

Chilmark house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$715

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

Chilmark house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$902

Gracious and Spacious Chilmark Home with a Pool

Chilmark house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$686

CHARMING COUNTRY HOME IN CHILMARK

Chilmark house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$500

Great rentals within 20 miles that match your search

Solera Victorian charm, ocean view, steps to beach

Oak Bluffs cottage

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

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Price per night from

$1,967

Seaside cottage

Falmouth cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$493

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$783

3 bedroom 2 bath Fully remodeled home

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$316

Contemporary 4 Bedroom House One Mile to Beach

New Seabury house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$831

Magnificent Contemporary on Exclusive Point

Falmouth house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$918

Charming Lambert's Cove Beach House

West Tisbury house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$431

Sweet Cottage in Woods Hole Village Steps to Beach

Woods Hole cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$431

Martha's Vineyard Rental

Edgartown house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$655

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

Oak Bluffs house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 19

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Price per night from

$6,890

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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Price per night from

$264

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

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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Price per night from

$173

Vineyard House - South Beach Down The Street

Edgartown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$345

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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Price per night from

$575

Oak Bluffs Contemporary Summer Home

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$361

Walk to Beach from 4 Bedroom Falmouth Village Home

Falmouth house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$517

Great Location, Beautiful Home

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$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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Price per night from

$1,148

Minutes to Menauhant Beach - Newly Furnished

Falmouth house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$431

New Cape House Steps to the Beach in East Falmouth

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$431

2+BR Renovated Gingerbread Cottage - Walk to All

Oak Bluffs house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$525

Bayside Beach house in Maravista, walk to beach

Teaticket house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$225

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

Edgartown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$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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Price per night from

$454

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Price per night from

$1,090

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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Price per night from

$574

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Price per night from

$746

Walk to Private Beach

Falmouth studio

  • Studio
  • 1 bathroom
  • sleeps 4

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Price per night from

$156

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Price per night from

$3,844

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

Viewing 38 of 268
rentals in Chilmark

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