Old Market Square Winter Rentals & Holiday Homes

Discover winter rentals Old Market Square - We found 181 exact matches

About Old Market Square Winter Rental on SunSkiResorts

Planning a winter vacation in Old Market Square? Discover 181 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Old Market Square, MB 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 Old Market Square start at $141. The most popular properties in Old Market Square 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 Old Market Square, 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 Old Market Square and unlock incredible deals.

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Frequently Asked Questions About Old Market Square Winter Rentals

The average cost for winter rentals in Old Market Square is $141 per night. SunSki has a wide list of great winter places to stay near Old Market Square 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 Old Market Square that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Old Market Square on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Old Market Square to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 181 private swimming pools or indoor pools accommodations near Old Market Square along with other great amenities.

About 181 holiday rentals in Old Market Square 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 Old Market Square for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Old Market Square with all the best amenities for your next trip.