Chilmark Vacation Rentals

Compare 1,955 available properties from 20 providers
Chilmark
Anytime
2 guests
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Best Vacation Home Deals in Chilmark

-18%
e.g. 10/5 - 10/12
House ∙ 8 guests ∙ 3 bedrooms
Chilmark, Dukes County, Massachusetts, United States
from $612 $749
VRBO
5.0
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-30%
e.g. 9/7 - 9/14
House ∙ 8 guests ∙ 4 bedrooms
Chilmark, Dukes County, Massachusetts, United States
from $385 $550
VRBO
5.0
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-17%
e.g. 3/16 - 3/23
House ∙ 10 guests ∙ 4 bedrooms
Chilmark, Dukes County, Massachusetts, United States
from $1,036 $1,251
VRBO
View deal

Find the ideal vacation rental for as little as $74 per night by searching among the 1,955 options being offered in Chilmark. With HomeToGo, you can directly compare the prices of each available property to find the best price and save up to 30%.

Recommended Vacation Rentals in Chilmark

Find your perfect vacation rental in Chilmark: from $74 per night

House ∙ 2 guests ∙ 1 bedroom
Chilmark, Dukes County, Massachusetts, United States
from $358
VRBO
5.0
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House ∙ 4 guests ∙ 2 bedrooms
Chilmark, Dukes County, Massachusetts, United States
from $413
VRBO
5.0
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House ∙ 5 guests ∙ 3 bedrooms
Chilmark, Dukes County, Massachusetts, United States
from $215
VRBO
4.5
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House ∙ 5 guests ∙ 2 bedrooms
Chilmark, Dukes County, Massachusetts, United States
from $319
VRBO
5.0
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House ∙ 4 guests ∙ 2 bedrooms
Chilmark, Dukes County, Massachusetts, United States
from $279
VRBO
5.0
View deal
House ∙ 5 guests ∙ 2 bedrooms
Chilmark, Dukes County, Massachusetts, United States
from $296
VRBO
5.0
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House ∙ 4 guests ∙ 2 bedrooms
Chilmark, Dukes County, Massachusetts, United States
from $111
VRBO
5.0
View deal
House ∙ 2 guests ∙ 1 bedroom
Chilmark, Dukes County, Massachusetts, United States
from $239
Airbnb
5.0
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Apartment ∙ 2 guests ∙ 1 bedroom
Chilmark, Dukes County, Massachusetts, United States
from $229
Airbnb
4.5
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Vacation Rentals With Fireplaces

Fireplace
House ∙ 5 guests ∙ 3 bedrooms
Chilmark, Dukes County, Massachusetts, United States
from $264
VRBO
4.7
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Fireplace
Cottage ∙ 9 guests ∙ 5 bedrooms
Chilmark, Dukes County, Massachusetts, United States
from $365
Airbnb
4.5
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Fireplace
House ∙ 8 guests ∙ 5 bedrooms
Chilmark, Dukes County, Massachusetts, United States
from $1,535
Airbnb
5.0
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Vacation Homes With Fishing Spots Nearby

Fishing
House ∙ 4 guests ∙ 2 bedrooms
Chilmark, Dukes County, Massachusetts, United States
from $405
VRBO
4.8
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Fishing
House ∙ 10 guests ∙ 5 bedrooms
Chilmark, Dukes County, Massachusetts, United States
from $872
VRBO
4.4
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Fishing
House ∙ 8 guests ∙ 4 bedrooms
Chilmark, Dukes County, Massachusetts, United States
from $429
VRBO
5.0
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Dog-Friendly Vacation Rentals

Pet-friendly
House ∙ 11 guests ∙ 5 bedrooms
Chilmark, Dukes County, Massachusetts, United States
from $1,104
VRBO
5.0
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Pet-friendly
House ∙ 8 guests ∙ 4 bedrooms
Chilmark, Dukes County, Massachusetts, United States
from $721
Airbnb
5.0
View deal
Pet-friendly
House ∙ 14 guests ∙ 5 bedrooms
Chilmark, Dukes County, Massachusetts, United States
from $500
Airbnb
4.5
View deal
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Popular Rental Amenities in Chilmark

  • Kitchen (177)
  • Internet (163)
  • TV (160)
  • Washer (136)
  • Grill (116)
  • No smoking (108)
  • Microwave (108)
  • Dishwasher (102)
  • AC (82)
  • Fireplace (73)
  • No pets (72)
  • Parking (70)
Use filters to look for an offer fitting your needs among all of the rentals in Chilmark. You can easily search and find a vacation rental fitting your criteria in Chilmark if you want to tune out with some TV time or you can't imagine a vacation without internet, as most accommodations provide "TVs" and "internet." It is also possible to find a property in Chilmark if you want a rental with a pool as 178 of the listed accommodations there offer "pools."

The Weather in Chilmark

41°
27°
39°
25°
46°
28°
57°
37°
66°
48°
73°
55°
81°
64°
79°
61°
75°
54°
64°
46°
54°
37°
48°
34°
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Check out the climate diagram for Chilmark. In July maximum temperatures go higher than 80°. Conversely, February is the coolest month in Chilmark, with temperatures going under 24° The rainiest month is January while the driest month is August.

Accommodations in Chilmark

In Chilmark, nearly all of the 1,955 accommodation types are house rentals, which represent 94.34% of its listed properties. Interestingly, specific accommodation type, this specific type of property is $841 a night, with an average area of 2,050 ft². Moreover, if you are going in a group of 8, house rentals are the ideal property type in Chilmark, as they usually welcome this exact group size. If you would prefer to book a different accommodation type, you could consider private rooms, which are the other most frequent property type in Chilmark. Private rooms in Chilmark are 860 ft² on average, with prices averaging $226 per night.

Enjoy blissful beaches at a Chilmark vacation home

Vacation homes in Chilmark, Massachusetts, snuggle between Providence, Boston, and internationally famous natural beauty spots such as Martha's Vineyard. With a vacation home here, you can enjoy some of the finest cultural and intellectual scenes in the country as well as the state's superlatively beautiful coastline.

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Art & Culture

Hang out at Edgar Allen Poe’s old haunts

Providence sits at the confluence of several rivers – fitting, as it is also a confluence of culture. While Boston has Harvard, Providence is home to Brown University, another prominent Ivy League institution. Its historic streets are filled with charming lanes, galleries, and theaters where you can experience the latest outpourings from creative locals. Rhode Island School of Design is also situated here, and the Providence Athenaeum's unique architecture is not to be missed. The famously eccentric poet Edgar Allen Poe allegedly used to pursue women here!

Family Activities

Into the wild

Children love the animals at Nomans Land Island National Wildlife Center. Approximately 640 acres of island stretch before you, full of exciting wildlife such as raptors, songbirds, and double-crested cormorants. Wander the trails through goldenrod and American beachgrass as you take in the views. Martha's Vineyard, a charming enclave that attracts creatives, is miles away from the grip of commercialization. Menemsha Harbor, featured in the film Jaws, is ringed with fishing boats and sublime views over the sparkling water.

Local Attractions

Venture to Boston

Boston, just a two-and-a-half-hour drive along the coast from your vacation home, is well worth the journey. With Harvard University, the Boston Tea Party Ships & Museum, and Boston Public Library all vying for your attention, you'll be glad you came. Watch the Red Sox play at Fenway Park in the summer months, or head to MIT to see some of the world's most famous innovations. The intellectual scope of the city is matched only by its architectural elegance.

We compare more than 600 providers, including:

Booking.com Vacation Rentals in Chilmark VRBO Vacation Rentals in Chilmark HomeAway Vacation Rentals in Chilmark Airbnb Vacation Rentals in Chilmark TripAdvisor Vacation Rentals in Chilmark VacationRentals.com Vacation Rentals in Chilmark HouseTrip Vacation Rentals in Chilmark FlipKey Vacation Rentals in Chilmark 9flats.com Vacation Rentals in Chilmark VaycayHero Vacation Rentals in Chilmark PerfectPlaces.com Vacation Rentals in Chilmark Homestay.com Vacation Rentals in Chilmark Only-apartments Vacation Rentals in Chilmark Interhome Vacation Rentals in Chilmark Bedycasa Vacation Rentals in Chilmark Novasol Vacation Rentals in Chilmark HomeEscape Vacation Rentals in Chilmark

Vacation Destinations Near Chilmark