1. USA
  2. New York
  3. Chatham
  4. Winter Rental

Chatham Winter Rentals & Holiday Homes

Discover winter rentals Chatham - We found 30 exact matches

About Chatham Winter Rental on SunSkiResorts

Planning a winter vacation in Chatham? Discover 30 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Chatham, NY perfect for your seasonal escape. Our listings include private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments. SunSki's winter vacation homes feature top amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Winter accommodations in Chatham start at US $545. The most popular properties in Chatham include cabins, bungalows, and rental homes. Planning a snowboarding adventure? Explore our snowboard-friendly ski resorts, chalets, and cabins available for short-term or long-term stays. Whether it's a weekend getaway, monthly retreat, or an extended stay, SunSki ensures a memorable winter trip.

To book your winter vacation homes in Chatham, visit SunSki's filter option, enter your travel dates, narrow down your preferences, and choose from our extensive list of rentals hassle-free. Explore our interactive map to uncover all accommodations in or around Chatham and unlock incredible deals.

Show more
Show less

Frequently Asked Questions About Chatham Winter Rentals

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

The average cost for winter rentals in Chatham is $545 per night. SunSki has a wide list of great winter places to stay near Chatham 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 Chatham that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Chatham on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Chatham to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 30 private swimming pools or indoor pools accommodations near Chatham along with other great amenities.

About 30 holiday rentals in Chatham 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 Chatham for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Chatham with all the best amenities for your next trip.