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Chilmark Rentals

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Chilmark Rentals

About Chilmark

56 houses

LEWDG - Waterfront, Waterview, Walk to Beach, Hi Speed Internet, WiFi

Chilmark house

4 bedrooms / 2 bathrooms / Sleeps 6

$430

1 / 23

$1,264

1 / 37

Quiet home with beach & dock access, peek-a-boo ocean views!

Chilmark house

2 bedrooms / 1 bathroom / Sleeps 4

$93

1 / 29

ALDEB - Waterfront, Hi Speed Internet

Chilmark house

2 bedrooms / 1 bathroom / Sleeps 4

$357

1 / 24

Charming Chilmark 3 Bedroom 3 Bath Vacation Home

Chilmark house

3 bedrooms / 3 bathrooms / Sleeps 6

$346

1 / 10

$329

1 / 12

HAUCJ -

Chilmark house

5 bedrooms / 4 bathrooms / Sleeps 12

$357

1 / 24

FERRN - Summer in Chilmark, Private Location, Large Deck w Outdoor Dining Area,

Chilmark house

3 bedrooms / 2 bathrooms / Sleeps 6

$400

1 / 19

WATERFRONT VINEYARD CONTEMPORARY HOME LOCATED ON TISBURY GREAT POND

Chilmark house

5 bedrooms / 5 bathrooms / Sleeps 10

$1,786

1 / 30

Chilmark Cottage

Chilmark house

3 bedrooms / 2 bathrooms / Sleeps 6

$168

1 / 5

LEWID - Menemsha Waterfront, Magnificent Views and Private Location, WiFi

Chilmark house

3 bedrooms / 2 bathrooms / Sleeps 6

$571

1 / 26

LORUJ - Spacious Ocean View Home, Private Association Beach - South Shore - Inq

Chilmark house

4 bedrooms / 3 bathrooms / Sleeps 8

$700

1 / 18

ROSSR - Chilmark, Waterview, Private Pool

Chilmark house

4 bedrooms / 3 bathrooms / Sleeps 8

$1,179

1 / 10

BLASD - A Gem in Chilmark, Impeccably Maintained Home, Multiple Decks and Patio

Chilmark house

4 bedrooms / 4 bathrooms / Sleeps 8

$500

1 / 33

$929

1 / 34

Chilmark Vacation Home with Lovely Views and Pool

Chilmark house

6 bedrooms / 4 bathrooms / Sleeps 12

$857

1 / 19

CHARMING WATERFRONT COTTAGE WITH WONDERFUL VIEWS OF THE ATLANTIC OCEAN

Chilmark house

2 bedrooms / 1 bathroom / Sleeps 4

$357

1 / 14

SPACIOUS AND COMFORTABLE CHILMARK CAPE WITH CENTRAL AIR CONDITIONING

Chilmark house

4 bedrooms / 2 bathrooms / Sleeps 8

$179

1 / 11

ALDEM - Gorgeous Waterfront Home, Magnificent Views of the Atlantic, Great Kaya

Chilmark house

3 bedrooms / 2 bathrooms / Sleeps 8

$500

1 / 42

MEINT - Stately Historic Chilmark Home, All Newly updated to Luxury Standards, P

Chilmark house

5 bedrooms / 3 bathrooms / Sleeps 10

$571

1 / 41

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

Chilmark house

5 bedrooms / 4 bathrooms / Sleeps 12

$787

1 / 30

TEELK - Menemsha Village Cottage, Walk to Menemsha Beach, A/C, WiFi

Chilmark house

4 bedrooms / 3 bathrooms / Sleeps 8

$350

1 / 23

ENRIP - Privacy, Lovely Yard, Short Drive to Lucy Vincent Beach

Chilmark house

5 bedrooms / 3 bathrooms / Sleeps 12

$500

1 / 11

ATLANTIC OCEAN BREEZES, GLORIOUS VIEWS!

Chilmark house

4 bedrooms / 4 bathrooms / Sleeps 8

$429

1 / 22

SAWYW - Designer Luxury with Oustanding Atlantic Ocean Views, Private Beaches,

Chilmark house

5 bedrooms / 5 bathrooms / Sleeps 10

$1,566

1 / 33

Gracious and Spacious Chilmark Home with a Pool

Chilmark house

4 bedrooms / 3 bathrooms / Sleeps 8

$571

1 / 16

KOGAB - Chilmark, South Road, 3 Miles to Lucy Vincent Beach, WiFi

Chilmark house

4 bedrooms / 2 bathrooms / Sleeps 8

$436

1 / 28

MCAUM - Thoughtfull Architectual Design set Amidst an Estate Property, Bordered

Chilmark house

4 bedrooms / 3 bathrooms / Sleeps 7

$929

1 / 36

CLASSIC VINEYARD FISHING VILLAGE VIEWS FROM THIS QUINTESSENTIAL COTTAGE

Chilmark house

2 bedrooms / 1 bathroom / Sleeps 4

“Location, location, location” We had a wonderful week at the Klimm house. So much so, we are renting it again next year. The house is very cute and the fact that you can walk to the beach, the market, to The Bite - what more can you ask for? The up

$143

1 / 12

MICHA - Chilmark Hilltop Luxury Home, A/C, Wifi Internet

Chilmark house

5 bedrooms / 4 bathrooms / Sleeps 8

$1,143

1 / 33

ARCHITECTURAL AWARD WINNING HOME WITH PANORAMIC VIEWS OF THE VINEYARD SOUND

Chilmark house

6 bedrooms / 4 bathrooms / Sleeps 10

$1,071

1 / 17

BRESP - Waterview, Association Beach

Chilmark house

6 bedrooms / 4 bathrooms / Sleeps 10

$1,214

1 / 23

HORNP - Squibnocket Farm Waterfront, Private Beach,

Chilmark house

4 bedrooms / 2 bathrooms / Sleeps 9

$1,714

1 / 33

CHARMING HOME W/VIEWS OF VINEYARD SOUND & ELIZABETH ISLANDS

Chilmark house

4 bedrooms / 2 bathrooms / Sleeps 8

$286

1 / 8

ENJOY OCEAN VIEWS FROM THIS CHILMARK HOME

Chilmark house

4 bedrooms / 2 bathrooms / Sleeps 8

$643

1 / 8

GIBBT - Large Deck, Wifi, A/C, Conveniently Located in One of The Most Beautifu

Chilmark house

4 bedrooms / 2 bathrooms / Sleeps 8

$214

1 / 11

PERRG - North Slope Hilltop House. Private yard, Screeen Porch and Patio, All

Chilmark house

3 bedrooms / 2 bathrooms / Sleeps 6

$286

1 / 18

Spacious clapboard home with large yard and outdoor shower

Chilmark house

3 bedrooms / 2 bathrooms / Sleeps 6

Responds fast! avg. 3 hours 41 minutes

$280

1 / 36
Viewing 38 of 56

About Chilmark

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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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