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Chilmark Rentals

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426 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

$899

Family friendly beach house sleeps 12

Chilmark house

5 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$912

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

$229

Gracious and Spacious Chilmark Home with a Pool

Chilmark house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$693

Spectacular Chilmark Hilltop Ocean View

Chilmark cottage

5 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$515

CHARMING COUNTRY HOME IN CHILMARK

Chilmark house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$436

CHARMING HOME W/VIEWS OF VINEYARD SOUND & ELIZABETH ISLANDS

Chilmark house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$286

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

$456

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

Oak Bluffs house

5 bedrooms / 5 bathrooms / sleeps 19

Price per night from

$3,418

Panoramic ocean views, steps to beach & bike path

Falmouth house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$301

GREAT VACATION HOUSE-GREAT LOCATION TO SOUTH BEACH

Edgartown house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 29 minutes

Price per night from

$342

Charming 3br Getaway in Oak Bluffs

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$285

Summer Vacation Rental

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$416

Cape Cod - Great Views, walk to beach

Woods Hole house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$627

Waterfront Resort in Falmouth - 6/3/22 - 6/10/22

Falmouth apartment

1 bedroom / 2 bathrooms / sleeps 4

Price per night from

$171

Falmouth Cape Cod Summer Vacation Rental Waterview

Falmouth house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$171

Great Family Home, Close to South Beach, And Town

Edgartown house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 29 minutes

Price per night from

$325

Great Martha's Vineyard Island Cottage!

Edgartown house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 29 minutes

Price per night from

$309

Katama House "CLOSE TO THE BEACH"

Acushnet house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 29 minutes

Price per night from

$309

Vineyard House - South Beach Down The Street

Edgartown house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 29 minutes

Price per night from

$325

Quaint Island Setting,Personal Beach and Dock. Kayak, Paddle Board and/or Boat

Mashpee cottage

2 bedrooms / 1 bathroom / sleeps 8

“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

$342

X-Large Cape Cod Beach House

Falmouth house

7 bedrooms / 4 bathrooms / sleeps 16

Price per night from

$733

Falmouth Heights home steps to Beaches...Clean and Comfortable

Falmouth house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 9 minutes

Price per night from

$456

Oak Bluffs Contemporary Summer Home

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 44 minutes

Price per night from

$326

Walk to Beach from 4 Bedroom Falmouth Village Home

Falmouth house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$456

Marthas Vineyard, Edgartown, Katama area

Edgartown house

3 bedrooms / 2 bathrooms / sleeps 12

“Great Vineyard Vacation” This house is close to town walking distance to Katama General Store and The right Fork for breakfast. On the bus line and bike/walking path, yet private with a huge yard for afternoon games! We have come back year after year. This house has accomodated my daughter and her teenage friends for an impromptu long weekend, while also accomodating my 78 year old mom and my young children. Its family friendly, has a great outdoor shower, fully stocked kitchen and beautiful deck for morning coffee or evening happy hour. We keep coming back!

Responds fast! avg. 2 hours 38 minutes

Price per night from

$570

Waterfront, Tisbury Great Pond

West Tisbury house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$293

Cape Cod -Falmouth - Beachfront Olde Cape Cod Charm

Falmouth house

5 bedrooms / 3 bathrooms / sleeps 9

Price per night from

$597

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

Oak Bluffs cottage

6 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 20 minutes

Price per night from

$570

Minutes to Menauhant Beach - Newly Furnished

Falmouth house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$428

New Cape House Steps to the Beach in East Falmouth

Falmouth house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$428

Waterfront-Martha's Vineyard

Oak Bluffs house

4 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$399

Magnificent Contemporary on Exclusive Point

Falmouth house

3 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 2 hours 39 minutes

Price per night from

$570

437 State Road,

Aquinnah house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$529

Long Point Woods

West Tisbury house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$491

Charming Lambert's Cove Beach House

West Tisbury house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$371

Sweet Cottage in Woods Hole Village Steps to Beach

Woods Hole cottage

3 bedrooms / 1 bathroom / sleeps 5

Price per night from

$428

Viewing 38 of 426
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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