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943 Houses

33

Beautiful, historic farmhouse with shared dock on Chilmark Pond

Martha's Vineyard / Chilmark

Chilmark house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Car not necessary

Price per night from

$319

Price per night from

$319

24

HAUCJ -

Martha's Vineyard / Chilmark

Chilmark house

5 12 7 nights min

  • 5 bedrooms
  • sleeps 12
  • 7 nights min
  • Ask about children

Price per night from

$357

Price per night from

$357

18

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

Martha's Vineyard / Chilmark

Chilmark house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning

Price per night from

$700

Price per night from

$700

41

MEINW - Wade's Cove Waterfront Luxury Residence, Key to Private Hancock Beach,

Martha's Vineyard / Chilmark

Chilmark house

4 8 14 nights min

  • 4 bedrooms
  • sleeps 8
  • 14 nights min
  • Ask about children
  • Air conditioning

Price per night from

$1,429

Price per night from

$1,429

31

NEW LISTING! Oceanfront home w/deck, amazing sunset views & beach access-dogs OK

Martha's Vineyard / Chilmark

Chilmark house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Pet Friendly

Price per night from

$683

Price per night from

$683

26

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

Martha's Vineyard / Chilmark

Chilmark house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Ask about children

Price per night from

$571

Price per night from

$571

5

Chilmark Cottage

Martha's Vineyard / Chilmark

Chilmark house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$192

Price per night from

$192

37

NOBLM - Distinctive Luxury Summer Retreat, Private Tennis Courts, Private Associ

Martha's Vineyard / Chilmark

Chilmark house

5 9 7 nights min

  • 5 bedrooms
  • sleeps 9
  • 7 nights min
  • Ask about children
  • Air conditioning

Price per night from

$1,264

Price per night from

$1,264

17

SMITD - Top Side Cottage, set in the Iconic Village of Menemsha and Overlooking

Martha's Vineyard / Chilmark

Chilmark house

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Ask about children
  • Air conditioning

Price per night from

$214

Price per night from

$214

31

Chilmark Farmhouse with access to Hancock Beach

Martha's Vineyard / Chilmark

Chilmark house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$571

Price per night from

$571

10

ROSSR - Chilmark, Waterview, Private Pool

Martha's Vineyard / Chilmark

Chilmark house

4 8 14 nights min

  • 4 bedrooms
  • sleeps 8
  • 14 nights min
  • Swimming pool
  • Ask about children

Price per night from

$1,179

Price per night from

$1,179

(1) Excellent 

10

Charming Chilmark 3 Bedroom 3 Bath Vacation Home

Martha's Vineyard / Chilmark

Chilmark house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Car not necessary

Price per night from

$395

Price per night from

$395

33

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

Martha's Vineyard / Chilmark

Chilmark house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning

Price per night from

$786

Price per night from

$786

11

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

Martha's Vineyard / Chilmark

Chilmark house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning

Price per night from

$179

Price per night from

$179

41

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

Martha's Vineyard / Chilmark

Chilmark house

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Ask about children
  • Air conditioning

Price per night from

$571

Price per night from

$571

11

SPACIOUS AND COMFORTABLE CHILMARK CAPE WITH CENTRAL AIR CONDITIONING

Martha's Vineyard / Chilmark

Chilmark house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$179

Price per night from

$179

(1) Very Good 

29

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

Martha's Vineyard / Chilmark

Chilmark house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Car not necessary

Price per night from

$90

Price per night from

$90

30

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

Martha's Vineyard / Chilmark

Chilmark house

5 12 7 nights min

  • 5 bedrooms
  • sleeps 12
  • 7 nights min
  • Nearest beach 4 mi
  • Child Friendly
  • Pet Friendly

Price per night from

$898

Price per night from

$898

23

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

Martha's Vineyard / Chilmark

Chilmark house

4 6 7 nights min

  • 4 bedrooms
  • sleeps 6
  • 7 nights min
  • Ask about children

Price per night from

$429

Price per night from

$429

19

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

Martha's Vineyard / Chilmark

Chilmark house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning

Price per night from

$400

Price per night from

$400

36

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

Martha's Vineyard / Chilmark

Chilmark house

4 7 7 nights min

  • 4 bedrooms
  • sleeps 7
  • 7 nights min
  • Ask about children
  • Air conditioning

Price per night from

$929

Price per night from

$929

20

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

Martha's Vineyard / Chilmark

Chilmark house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$659

Price per night from

$659

34

HERGT - Luxury Retreat Chilmark, Key to Quansoo Private Association Beach, Set o

Martha's Vineyard / Chilmark

Chilmark house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning

Price per night from

$1,071

Price per night from

$1,071

33

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

Martha's Vineyard / Chilmark

Chilmark house

5 8 7 nights min

  • 5 bedrooms
  • sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning

Price per night from

$1,143

Price per night from

$1,143

9

Family friendly beach house sleeps 12

Martha's Vineyard / Chilmark

Chilmark house

5 12 7 nights min

  • 5 bedrooms
  • sleeps 12
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$916

Price per night from

$916

33

HORNP - Squibnocket Farm Waterfront, Private Beach,

Martha's Vineyard / Chilmark

Chilmark house

4 9 7 nights min

  • 4 bedrooms
  • sleeps 9
  • 7 nights min
  • Ask about children

Price per night from

$1,714

Price per night from

$1,714

12

SPANM - Sweet Chilmark Cottage, Spacious Screened Porch and Deck Area, Private L

Martha's Vineyard / Chilmark

Chilmark house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Ask about children

Price per night from

$329

Price per night from

$329

19

Chilmark Vacation Home with Lovely Views and Pool

Martha's Vineyard / Chilmark

Chilmark house

6 12 min stay varies

  • 6 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Ask about children

Price per night from

$857

Price per night from

$857

(1) Very Good 

12

CLASSIC VINEYARD FISHING VILLAGE VIEWS FROM THIS QUINTESSENTIAL COTTAGE

Martha's Vineyard / Chilmark

Chilmark house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Ask about children
“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
…see more

Price per night from

$143

Price per night from

$143

36

Spacious clapboard home with large yard and outdoor shower

Martha's Vineyard / Chilmark

Chilmark house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly
  • Car not necessary

Price per night from

$386

Price per night from

$386

28

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

Martha's Vineyard / Chilmark

Chilmark house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Ask about children

Price per night from

$436

Price per night from

$436

13

JAFFP - Cottage by the Sea, Ocean and Beachfront Location, Private one of a Kin

Martha's Vineyard / Chilmark

Chilmark house

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Ask about children

Price per night from

$257

Price per night from

$257

22

Spectacular Chilmark Hilltop Ocean View

Martha's Vineyard / Chilmark

Chilmark cottage

5 9 5 nights min

  • 5 bedrooms
  • sleeps 9
  • 5 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$516

Price per night from

$516

11

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

Martha's Vineyard / Chilmark

Chilmark house

5 12 7 nights min

  • 5 bedrooms
  • sleeps 12
  • 7 nights min
  • Ask about children

Price per night from

$500

Price per night from

$500

23

BRESP - Waterview, Association Beach

Martha's Vineyard / Chilmark

Chilmark house

6 10 7 nights min

  • 6 bedrooms
  • sleeps 10
  • 7 nights min
  • Ask about children

Price per night from

$1,214

Price per night from

$1,214

16

Gracious and Spacious Chilmark Home with a Pool

Martha's Vineyard / Chilmark

Chilmark house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$571

Price per night from

$571

13

Charming Chilmark Cottage

Martha's Vineyard / Chilmark

Chilmark house

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Child Friendly

Price per night from

$410

Responds fast!
avg. 1 hour 17 minutes

Price per night from

$410

31

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

Martha's Vineyard / Chilmark

Chilmark house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$1,429

Price per night from

$1,429

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.