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Madison Winter Rentals & Holiday Homes

Discover winter rentals Madison - We found 19 exact matches

About Madison Winter Rental on SunSkiResorts

Planning a winter vacation in Madison? Discover 19 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Madison, SD 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 Madison start at $246. The most popular properties in Madison 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 Madison, 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 Madison and unlock incredible deals.

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Frequently Asked Questions About Madison Winter Rentals

The average cost for winter rentals in Madison is $246 per night. SunSki has a wide list of great winter places to stay near Madison 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 Madison that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Madison on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Madison to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 19 private swimming pools or indoor pools accommodations near Madison along with other great amenities.

About 19 holiday rentals in Madison 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 Madison for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Madison with all the best amenities for your next trip.