Far Southwest Side Winter Rentals & Holiday Homes

Discover winter rentals Far Southwest Side - We found 13 exact matches

About Far Southwest Side Winter Rental on SunSkiResorts

Planning a winter vacation in Far Southwest Side? Discover 13 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Far Southwest Side, 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 Far Southwest Side start at US $283. The most popular properties in Far Southwest Side 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 Far Southwest Side, 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 Far Southwest Side and unlock incredible deals.

Show more
Show less

Frequently Asked Questions About Far Southwest Side Winter Rentals

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

The average cost for winter rentals in Far Southwest Side is $283 per night. SunSki has a wide list of great winter places to stay near Far Southwest Side 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 Far Southwest Side that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Far Southwest Side on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Far Southwest Side to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 13 private swimming pools or indoor pools accommodations near Far Southwest Side along with other great amenities.

About 13 holiday rentals in Far Southwest Side 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 Far Southwest Side for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Far Southwest Side with all the best amenities for your next trip.