Wisconsin Winter Rentals & Holiday Homes

There are a lot of options in Wisconsin. If you plan on staying in the Wisconsin 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:

• Secluded, Romantic, Family Friendly and Cozy, Last House in the Valley.
• Nature Lover's Paradise In The Driftless Area Of Southern Wisconsin, USA.
• The Honey Barn & Honey House LLC
• A Home Away from Home in the Quaint Village of New Glarus
• Private Beach & Pier Lake Front w/Fireplace on Lake Como - Walk to Mars Resort!
• Immaculate Hand-Hewn Log Cabin ~ Private Wooded Setting In Egg Harbor
• Legendary Moose Lodge
• A Pleasant Retreat- No Cleaning Fee & New Discounts
• Arcadian Cabin at Bishop Branch, creek-front, public land access, great location
• Main Street Lodge

The average cost for winter rentals in Wisconsin is $439 per night. Ownerdirect has a wide list of great winter places to stay near Wisconsin 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 that allow you to bring your pet or dog:

• Inn at the River
• Stunning Door County Cabin In The Woods, Wi-Fi, Firepit, Fireplace, Game Room
• Shane Acres Country Inn
• 515Escape - Near downtown, private backyard, firepit, bbq, fun!

See all pet-friendly vacation rentals in Wisconsin on Ownerdirect

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Wisconsin to find what works for you.

As of 2026, the data from Ownerdirect shows that there are over 18437 private swimming pools or indoor pools accommodations near Wisconsin along with other great amenities.