Chilmark Rentals

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Chilmark Farmhouse with access to Hancock Beach

Chilmark house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$714

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

Chilmark house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$900

Gracious and Spacious Chilmark Home with a Pool

Chilmark house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$686

CHARMING COUNTRY HOME IN CHILMARK

Chilmark house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$436

Great rentals within 20 miles that match your search

“Gingerbread House”, water views, large porch!

Oak Bluffs cottage

  • 4 bedrooms
  • 1 bathroom
  • sleeps 8

Price per night from

$687

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

Oak Bluffs house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 19

Price per night from

$6,870

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.

Price per night from

$252

Charming 3br Getaway in Oak Bluffs

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$344

Waterfront Resort in Falmouth - 6/4/23-6/11/23

Falmouth apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 8 minutes

Price per night from

$172

Clean, comfortable ranch with lots of amenities

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$544

“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.

Price per night from

$344

Falmouth Heights steps to Beaches...Clean and Comfortable

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$458

Oak Bluffs Contemporary Summer Home

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$328

Walk to Beach from 4 Bedroom Falmouth Village Home

Falmouth house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$516

Marthas Vineyard, Edgartown, Katama area 4 bedrooms

Edgartown house

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$573

Cape Cod -Falmouth - Beachfront Olde Cape Cod Charm

Falmouth house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 9

Price per night from

$500

Great Location, Beautiful Home

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$737

Ocean, lake, harbor & parkview Vineyard cottage w/AC

Oak Bluffs cottage

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$1,145

New Cape House Steps to the Beach in East Falmouth

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$430

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

Edgartown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$487

Immaculate Spacious Cape House with all the extras

Teaticket house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$229

Spectacular Martha's Vineyard Island Home!

Oak Bluffs townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

Responds fast! avg. 3 hours 34 minutes

Price per night from

$453

Rent This Beautiful Country Home In Historic Christiantown

West Tisbury house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$687

Paradise in Oak Bluffs.

Oak Bluffs house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 14

Price per night from

$2,456

Price per night from

$1,088

Falmouth! Private Ocean Beach! Stunning Views to Martha's Vineyard!

Teaticket house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

Price per night from

$508

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

Oak Bluffs house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$573

Solera Victorian charm, ocean view, steps to beach

Oak Bluffs cottage

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Price per night from

$1,963

Seaside cottage

Falmouth cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$492

Cape Cod Charm in Falmouth Village

Falmouth studio

  • Studio
  • 1 bathroom
  • sleeps 4

Price per night from

$373

Excellent location on Martha's Vineyard

Edgartown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$630

Price per night from

$180

Waterfront, Quiet 3 BR Cape-Walk to Beach

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$630

3 bedroom 2 bath Fully remodeled home

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$315

AMAZING BEACH COTTAGE AVAILABLE AUG 5 -12

Westport Point house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 17 minutes

Price per night from

$540

Contemporary 4 Bedroom House One Mile to Beach

New Seabury house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$829

Magnificent Contemporary on Exclusive Point

Falmouth house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$916

437 State Road,

Aquinnah house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$796

Viewing 38 of 307
rentals in Chilmark

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About Chilmark

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 vacation destinations in New England, there is no shortage of vacation 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 vacation 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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