Upper South Side Winter Rentals & Holiday Homes

Discover winter rentals Upper South Side - We found 440 exact matches

About Upper South Side Winter Rental on SunSkiResorts

Planning a winter vacation in Upper South Side? Discover 440 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Upper South Side, BC 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 Upper South Side start at US $413. The most popular properties in Upper South 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 Upper South 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 Upper South Side and unlock incredible deals.

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Frequently Asked Questions About Upper South Side Winter Rentals

There are a lot of options in Upper South Side. If you plan on staying in the Upper South 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 Upper South Side:

The average cost for winter rentals in Upper South Side is $413 per night. SunSki has a wide list of great winter places to stay near Upper South 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 Upper South Side that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Upper South Side on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Upper South Side to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 440 private swimming pools or indoor pools accommodations near Upper South Side along with other great amenities.

About 440 holiday rentals in Upper South 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 Upper South Side for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Upper South Side with all the best amenities for your next trip.