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Chilmark Rentals

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453 Houses

Chilmark Farmhouse with access to Hancock Beach

Chilmark house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$571

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

Chilmark house

5 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$900

Family friendly beach house sleeps 12

Chilmark house

5 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$894

SPACIOUS AND COMFORTABLE CHILMARK CAPE WITH CENTRAL AIR CONDITIONING

Chilmark house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$214

4 Bedroom on 5 Acres of Woodlands with Fresh Eggs and Chickens

Chilmark house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$657

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 upstairs bedrooms are very small, but we didn't spend much time there. I do wish that we had found the home in a cleaner condition. It was very dusty & musty. I did a thorough cleaning and dusting of the whole house before we could truly relax and enjoy the rest of the vacation. The upstairs carpet really needs to be replaced/removed. We had more than one allergy flareup while there, which I think was due to the carpet. But again - you can't beat the location.

Price per night from

$243

Luxury Expanded Cape on Wade's Cove & Key to Hancock Beach

Chilmark house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,429

Gracious and Spacious Chilmark Home with a Pool

Chilmark house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$1,139

Spectacular Chilmark Hilltop Ocean View

Chilmark cottage

5 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$511

CHARMING COUNTRY HOME IN CHILMARK

Chilmark house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$643

ARCHITECTURAL AWARD WINNING HOME WITH PANORAMIC VIEWS OF THE VINEYARD SOUND

Chilmark house

6 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$1,071

CHARMING HOME W/VIEWS OF VINEYARD SOUND & ELIZABETH ISLANDS

Chilmark house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$286

Spectacular Home with Waterviews of Vineyard Sound and Elizabeth Islands

Chilmark house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$1,357

Great rentals within 20 miles that match your search

Private Twin Room in Cozy Cottage

Oak Bluffs house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$389

Guest Room in a Cozy Cottage

Oak Bluffs private room

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$389

Winnetu Oceanside Resort Duplex K-4

Edgartown townhouse

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$1,143

X-Large Cape Cod Beach House

Falmouth house

7 bedrooms / 4 bathrooms / sleeps 16

Responds fast! avg. 42 minutes

Price per night from

$833

Oak Bluffs Home walk to town

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$463

AMAZING BEACH COTTAGE AVAILABLE AUG 5 -12

Westport Point house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$610

Bayside Beach house in Maravista, walk to beach

Teaticket house

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$254

Charming Cape Home/Walk to Beach

Falmouth house

3 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$545

Cape Cod Charm in Falmouth Village

Falmouth studio

Studio / 1 bathroom / sleeps 4

Price per night from

$421

Monthly rental on Martha’s Vineyard

West Tisbury house

4 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$314

Falmouth Cape Cod Summer Vacation Rental Waterview

Falmouth house

2 bedrooms / 1 bathroom / sleeps 7

Price per night from

$181

in town studio apartment close to everything

Edgartown apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$298

Lovely clapboard home in a private setting in the heart of town

Oak Bluffs house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$325

Luxury waterfront estate w/incredible gardens & entertaining spaces

Oak Bluffs house

6 bedrooms / 6 bathrooms / sleeps 10

Price per night from

$1,766

New home w/ deck, firepit & vineyard - near 3 beaches/Great Pond!

Waquoit house

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$365

Two-level house near the ocean & downtown - walk to Oak Bluffs, 1 dog OK!

Oak Bluffs house

2 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$598

Dog-friendly, two-level house near the ocean w/deck & grill. Walk to town!

Oak Bluffs house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$647

Newly built home w/ gourmet kitchen, furnished patio & grill - 1 dog OK!

Oak Bluffs house

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$778

Gorgeous 3BD/2BA Vacation House in the Vineyard

West Tisbury house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$244

Sun Sand and Sea- Architects House near Pond

Edgartown house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$569

Solera Victorian charm, ocean view, steps to beach

Oak Bluffs cottage

4 bedrooms / 3 bathrooms / sleeps 9

Price per night from

$1,011

Sweet Cottage in Woods Hole Village Steps to Beach

Woods Hole cottage

3 bedrooms / 1 bathroom / sleeps 5

Price per night from

$433

Oak Bluffs Contemporary Summer Home

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 27 minutes

Price per night from

$334

2+BR Renovated Gingerbread Cottage - Walk to All

Oak Bluffs house

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 1 hour 17 minutes

Price per night from

$581

Walk to Beach from 4 Bedroom Falmouth Village Home

Falmouth house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$461

Viewing 38 of 453
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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