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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Best Vacation Home Deals in Chilmark
Save up to 77%
Find the ideal vacation rental for as little as $200 per night by searching among the 123 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 81%.
Top-Rated Rentals and Accommodations in Chilmark
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Recommended Vacation Rentals in Chilmark
Find your perfect vacation rental in Chilmark: from $200 per night
Budget-friendly Vacation Rentals in Chilmark
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Dog-Friendly Vacation Rentals
Bring Fido on your next trip and book a stay in one of these pet-friendly rentals in Chilmark!
Best vacation rentals with a balcony
Looking for a home with a balcony? Check out these vacation homes in Chilmark with their own private patios and balconies.
Apartments With Balconies or Patios
Looking for a home with a balcony? Check out these vacation homes in Chilmark with their own private patios and balconies.

Popular Rental Amenities in Chilmark
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 are looking for a pet-friendly rental or you want to stay cool in your vacation home, as most accommodations provide "Pets allowed" and "Air conditioning." It is also possible to find a property in Chilmark if you would like a smoking room as 2 of the listed accommodations there offer "Smoking."
The Weather in Chilmark
Check out the climate diagram for Chilmark. In July maximum temperatures go higher than 81°. Conversely, February is the coolest month in Chilmark, with temperatures going under 25° The rainiest month is January while the driest month is August.
7-Day Weather Forecast in Chilmark
Accommodations for your vacation in Chilmark
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!
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.
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.
Information about vacation rentals in Chilmark
🏡 Vacation rentals available | 123 homes |
---|---|
💳 Possible discounts | up to 81% |
🌙 Nightly prices starting at | $200 |
⭐ Popular amenities | Pets allowed, Air conditioning and Pool |
🐾 Pet friendly homes | 49 homes |
Frequently Asked Questions
What is the nightly price for a vacation home in Chilmark?
The average accommodation in Chilmark is priced at $200 per night. If you would like to stay in a house rental, the average price is $1,669 per night. A cabin Chilmark will cost $672 per night on average.
How many vacation rentals are available to book in Chilmark?
There are 123 vacation homes in Chilmark to browse and rent for your next trip.
What are the most popular amenities for vacation rentals in Chilmark?
Three most popular amenities for home rentals in Chilmark include accommodations that have: Pets allowed, Air conditioning, and Pool.
How many vacation homes with a pool are in Chilmark?
Choose from 6 vacation rentals available in Chilmark.
Are dogs allowed in vacation rentals in Chilmark?
Sure, currently there are 49 vacation rentals in Chilmark that allow dogs and the average nightly rate is $2,054.
What's the best time of year to travel to Chilmark?
July and August are the warmest months in Chilmark with temperatures around 81 °F. The coldest months in Chilmark are February and January, with 25 °F on average.
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