Chilmark Rentals

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301 Houses

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

$500

Great rentals within 20 miles that match your search

Salt Water Front South of Rt. 28 with Private Dock and Amazing Views!

Teaticket house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$658

Price per night from

$3,831

Catherine's Meadow

Westport Point house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$327

Price per night from

$613

Walk to the Beach! NEW Hot Tub! Pets welcome!

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$387

The Amazing Bird Street House

Oak Bluffs house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 30 minutes

Price per night from

$1,030

CAPE COD'S BEST BEACH GETAWAY

Silver Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$1,030

Price per night from

$1,087

Stunning compound steps to Katama Bay, heated pool, dock & amenities

Edgartown house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 2 minutes

Price per night from

$1,430

Charming Apartment near golf course and beaches

Oak Bluffs apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 15 minutes

Price per night from

$492

Renovated Cottage near center and beaches

Edgartown house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 3 hours 15 minutes

Price per night from

$801

Greenehill~ Up-island 1800 Farmhouse

West Tisbury house

  • 4 bedrooms
  • 1 bathroom
  • sleeps 8

Price per night from

$1,144

Coastal Contemporary in Katama / South Beach / Edgartown / Bike Paths /

Edgartown house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$601

Between the Harbors

Oak Bluffs apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$486

New Construction beach retreat- 1/3 of a mile from Old Silver Beach

Silver Beach house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$1,024

Vineyard Charming Retreat near beaches and center

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 3 hours 15 minutes

Price per night from

$401

Spacious Beach House 6 Min Walk to Beach!

Waquoit house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$269

Style & Comfort at Modern Waterfront Home!

Waquoit house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$291

Deluxe suite at the oceanfront Surfside Resort

Falmouth hotel apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Price per night from

$458

#CozyBluffs 1 BR House in Historic Oak Bluffs - walk to town and ferry

Oak Bluffs house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

Price per night from

$801

Captain's Quarters charming oceanfront resort with swimming pool

Falmouth hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$458

41 Pelican Ln

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$460

Captain's Quarters - charming oceanfront resort with swimming pool

Falmouth hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$458

Sweetened Water Farm

Edgartown house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

Price per night from

$2,086

Rudders Cottage - entire home walking distance to ferry!

Vineyard Haven house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 6

Price per night from

$687

Sea Glenn Flowers Private home new to market

Vineyard Haven house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

Price per night from

$481

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

$781

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

Viewing 38 of 301
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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