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Wisconsin Dells Winter Rentals & Holiday Homes

Discover winter rentals Wisconsin Dells - We found 2071 exact matches

About Wisconsin Dells Winter Rental on SunSkiResorts

Planning a winter vacation in Wisconsin Dells? Discover 2071 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Wisconsin Dells, WI 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 Wisconsin Dells start at US $360. The most popular properties in Wisconsin Dells 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 Wisconsin Dells, 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 Wisconsin Dells and unlock incredible deals.

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Frequently Asked Questions About Wisconsin Dells Winter Rentals

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

The average cost for winter rentals in Wisconsin Dells is $360 per night. SunSki has a wide list of great winter places to stay near Wisconsin Dells 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 Wisconsin Dells that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Wisconsin Dells on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Wisconsin Dells to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 2071 private swimming pools or indoor pools accommodations near Wisconsin Dells along with other great amenities.

About 2071 holiday rentals in Wisconsin Dells 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 Wisconsin Dells for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Wisconsin Dells with all the best amenities for your next trip.