1. USA
  2. Massachusetts
  3. Chilmark
  4. Cottage Rentals

Chilmark Cottage Rentals & Holiday Homes

Find the best cottages in Chilmark - We found 18 exact matches

About Chilmark Cottage Rentals on SunSkiResorts

Searching for cottages to rent near Chilmark? SunSki features more than 18 cottages that are perfect for your next trip. Escape the snow and slopes and discover luxury cottage rentals just a few miles away from the lake or beach. These cottage rentals in Chilmark offer hot baths, are kid-friendly & family-friendly, and are situated near top local attraction spots, ensuring guests have the best travel experience possible. SunSki’s cottage listings come in all shapes and sizes, catering to large groups, friends, or couples in Chilmark.

Planning to travel to the lakeside, beach, or mountain area? SunSki’s cottage rentals offer a wide selection, providing direct access to the owners of these cottage rentals and offering you the best opportunity to find a good price.

SunSki boasts of 18 holiday cottages and places to stay in Chilmark. The site provides unique Airbnb, VRBO, ski-style cottages to fit your trip or getaway with your friends and family. Whether it's a weekend getaway, spring break, summer vacation, or annual holiday, all fit within your budget.

Show more
Show less

Frequently Asked Questions About Chilmark Rental Cottages

The average cost for a cottage rental in Chilmark is $579 per night. SunSki has a wide list of great cottages near Chilmark that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage rentals in Chilmark that allow you to bring your pet:

See all pet-friendly vacation rentals in Chilmark on SunSkiResorts

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Chilmark to find one that works for you.
As of 2026, the data from SunSkiResorts shows that there are Over 18 private swimming pools or cottages with indoor pools in the Chilmark area along with other great amenities.
About 18 cottages in Chilmark boast of premium hot tubs. Some of the popular places to stay with hot tubs include:See all holiday vacation rentals in Chilmark on SunSkiResorts
Yes, there are luxury cottages in Chilmark. Find more luxury, lakefront, winter, & last-minute cottage rentals near Chilmark.