1. USA
  2. Massachusetts
  3. Chilmark
  4. Winter Rental

Chilmark Winter Rentals & Cabins

Discover winter rentals Chilmark - We found 63 exact matches

About Chilmark Winter Rental on Cabinns.com

At Cabinns.com, we feature a wide range of listings for accommodations in Chilmark, MA that are perfect for your winter trip or seasonal escape. Our listings include hotels, private vacation homes, cabins, condos, villas, resorts, or pet-friendly apartments that travelers are sure to love. Cabinns.com winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Whether you are escaping the snow or running to it, Cabinns.com helps connect you to the best cabins, bungalows, lodges, and rent-by-owner homes, as well as the best places to stay in both sun and ski resorts. Cabinns.com will make your winter getaway an unforgettable experience.

Cabinns.com offers luxury finds for travelers planning on renting a place in Chilmark, to enjoy these benefits and to book your winter vacation homes, go to the Cabinns.com filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from a long list of incredible winter vacation rentals without hassle. Our interactive map is also available, so you can view destinations spanning the globe or around Chilmark and unlock even more amazing deals. Stay Close to Nature with Cabinns.com.

Show more
Show less

Frequently Asked Questions About Chilmark Winter Rentals

There are a lot of options in Chilmark. If you plan on staying in the Chilmark area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Chilmark:

The average cost for winter rentals in Chilmark is $1,841 per night. Cabinns.com has a wide list of great winter places to stay near Chilmark that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage/chalet rentals in Chilmark that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Chilmark on Cabinns.com

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Chilmark to find what works for you.
As of 2025, the data from Cabinns.com shows that there are over 63 private swimming pools or indoor pools accommodations near Chilmark along with other great amenities.

About 63 holiday rentals in Chilmark boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:

Yes, there are many luxury places to stay in Chilmark for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Chilmark with all the best amenities for your next trip.