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Holiday Lettings
> North America
> United States
> Massachusetts
> Martha's Vineyard
> Houses and Cottages in Chilmark

Houses in Chilmark and Cottages – Holiday Lettings - Holiday Rentals Chilmark

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£1 £750 -

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Filtered properties are rated either by Tripadvisor Vacation Rentals users, or by Vrbo users. Both rating systems are separate, and are depicted differently as shown in the key above. Tripadvisor performs checks on its reviews. Holiday Lettings and companies under Tripadvisor Group do not check Vrbo reviews.
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68 Holiday homes

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Holiday home in Chilmark

Chilmark house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

from £668 / night

£4,672 / week

1 / 30

Chilmark holiday home rental

Chilmark house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

from £268 / night

£1,870 / week

1 / 30

Chilmark holiday home rental

Chilmark house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

from £964 / night

£6,743 / week

1 / 30

Chilmark holiday cottage rental

Chilmark cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £249 / night

£1,744 / week

1 / 20

Holiday home in Chilmark

Chilmark house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £336 / night

£2,348 / week

1 / 15

Chilmark ski cottage to rent.

Chilmark cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

from £395 / night

£2,762 / week

1 / 14

Holiday home in Chilmark

Chilmark house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £441 / night

£3,084 / week

1 / 25

Chilmark ski home to rent.

Chilmark house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £475 / night

£3,320 / week

1 / 26

Chilmark holiday home rental

Chilmark house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £897 / night

£6,277 / week

1 / 30

Chilmark holiday home rental

Chilmark house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £330 / night

£2,307 / week

1 / 19

Ski home to rent in Chilmark

Chilmark house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £1,215 / night

£8,503 / week

1 / 25

Chilmark holiday home rental

Chilmark house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

from £512 / night

£3,585 / week

1 / 30

Chilmark holiday cottage rental

Chilmark cottage

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 9

from £513 / night

£3,590 / week

1 / 20

Chilmark holiday home rental

Chilmark house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 8

from £440 / night

£3,078 / week

1 / 30

Holiday home in Chilmark

Chilmark house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £642 / night

£4,493 / week

1 / 18

Holiday cottage in Chilmark

Chilmark cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £241 / night

£1,686 / week

1 / 18

Holiday home in Chilmark

Chilmark house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £586 / night

£4,102 / week

1 / 30

Chilmark holiday apartment rental

Chilmark apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £280 / night

£1,956 / week

1 / 7

Holiday cottage in Chilmark

Chilmark cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £335 / night

£2,342 / week

1 / 26

Chilmark holiday home rental

Chilmark house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

from £869 / night

£6,081 / week

1 / 30

Home letting in Chilmark

Chilmark house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

from £315 / night

£2,204 / week

1 / 24

Chilmark holiday home rental

Chilmark house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from £512 / night

£3,579 / week

1 / 24

Holiday home in Chilmark

Chilmark house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £606 / night

£4,240 / week

1 / 30

Holiday home in Chilmark

Chilmark house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £480 / night

£3,360 / week

1 / 30

Holiday home in Chilmark

Chilmark house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £881 / night

£6,162 / week

1 / 30

Chilmark ski home to rent.

Chilmark house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £1,135 / night

£7,940 / week

1 / 16

Holiday home in Chilmark

Chilmark house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £503 / night

£3,521 / week

1 / 30

Holiday home in Chilmark

Chilmark house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from £911 / night

£6,375 / week

1 / 16

Chilmark holiday home rental

Chilmark house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £710 / night

£4,965 / week

1 / 18

Home rental in Chilmark

Chilmark house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

from £642 / night

£4,493 / week

1 / 30

Holiday home rental

Chilmark house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £1,056 / night

£7,387 / week

1 / 30

Holiday home in Chilmark

Chilmark house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 10

from £512 / night

£3,579 / week

1 / 30

Holiday home in Chilmark

Chilmark house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £633 / night

£4,430 / week

1 / 26

Chilmark holiday home let

Chilmark house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

from £502 / night

£3,510 / week

1 / 15

Holiday home in Chilmark

Chilmark house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £833 / night

£5,828 / week

1 / 30

Chilmark holiday cottage rental

Chilmark cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from £512 / night

£3,579 / week

1 / 23

Chilmark ski home to rent.

Chilmark house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £1,583 / night

£11,081 / week

1 / 26

Home rental in Chilmark

Chilmark house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £436 / night

£3,049 / week

1 / 30

Holiday home in Chilmark

Chilmark house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £535 / night

£3,740 / week

1 / 11

Holiday home in Chilmark

Chilmark house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £400 / night

£2,796 / week

1 / 25

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Chilmark holidays

Just a few miles off the Cape Cod Peninsula, the town of Chilmark has rapidly become one of the most popular destinations in Martha's Vineyard. With beautiful views of the coast almost everywhere you turn, plenty of great seafood restaurants throughout town, and an abundance of art galleries and other cultural attractions, this isolated stretch of paradise has everything you need for a relaxing getaway.

The main strip of boutique shops and restaurants known as Main Street is right in the middle of Chilmark. However, many of the side streets have their own attractions including art galleries, beautiful historical buildings, and easy access to the beach.

While you're in Chilmark, be sure to make time for some of these must-see attractions and destinations in and around the area:

  • Waskosim's Rock Reservation: Head to this 184-acre preserve where you can stand atop one of the highest peaks on the island.
  • Chilmark Gallery: Observe a wide range of artwork from paintings and sculptures, all from some of the best local artists in Chilmark.
  • Go to the Beach: Lucy Vincent Beach is widely regarded as the most popular beach in Chilmark.
  • Try the local seafood: New England, and Martha's Vineyard specifically, are known for having some of the best fresh seafood in the country. Cook lobster from Menemsha Fish Market at home, or order fish from Homeport Restaurant while enjoying the sunset from the nearby dock.
  • Visit the Lighthouses: Cape Poge Lighthouse and Gay Head Lighthouse are just some of the nearby lighthouses that offer free sunset tours.
  • Go Biking: Many visitors are surprised to learn that Martha's Vineyard covers 100 square miles of mostly flat terrain, allowing for great cycling opportunities throughout the island.

Don't let the small size of the island fool you. Martha's Vineyard has many events throughout the year ranging from international sporting events to local music festivals, several of which are held in and around Chilmark. Watch some of the world's best fishermen compete at the Striped Bass and Bluefish Derby in September, the live performances from some of the island's top musicians during the Aquinnah Music Festival in August, or the elaborate Independence Day parade and fireworks performances throughout Chilmark in July.

As one of the most popular holiday destinations in New England, there is no shortage of holiday rentals to choose from year-round. Select a condo just steps from the beach and all the boutique shops in Chilmark, or rent a house in a more isolated setting surrounded by trees and natural scenery. No matter where you end up, there's bound to be a home that has everything you're looking for in a holiday getaway.

If you wish to explore the surrounding area, the Martha's Vineyard Transit Authority has several bus routes as well as ferries that are inexpensive and will take you anywhere on the island. Take a one-hour ferry ride to the beautiful beaches and charming towns of Cape Cod. Once you're there, head 90 miles east to the New England metropolis of Boston, full of quintessential American landmarks.

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