Cherry Valley Winter Rentals & Holiday Homes

Discover winter rentals Cherry Valley - We found 14 exact matches

About Cherry Valley Winter Rental on SunSkiResorts

Planning a winter vacation in Cherry Valley? Discover 14 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Cherry Valley, IL 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 Cherry Valley start at US $172. The most popular properties in Cherry Valley 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 Cherry Valley, 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 Cherry Valley and unlock incredible deals.

Show more
Show less

Frequently Asked Questions About Cherry Valley Winter Rentals

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

The average cost for winter rentals in Cherry Valley is $172 per night. SunSki has a wide list of great winter places to stay near Cherry Valley 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 Cherry Valley that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Cherry Valley on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Cherry Valley to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 14 private swimming pools or indoor pools accommodations near Cherry Valley along with other great amenities.

About 14 holiday rentals in Cherry Valley 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 Cherry Valley for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Cherry Valley with all the best amenities for your next trip.