Madison Winter Rentals & Holiday Homes
Discover winter rentals Madison - We found 415 exact matches
When do you want to travel?
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- Designated Smoking Area
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- Designated Smoking Area
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Frequently Asked Questions About Madison Winter Rental
What are the top rated Winter Rentals in Madison?
There are a lot of options in Madison. If you plan on staying in the Madison area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Madison:
- A Home Away from Home in the Quaint Village of New Glarus
- Clarance Gonstead Guest Cottage, Prairie Style, Stone & Tide Water Cypress
- Welcome To Your Home Away From Home. Welcome To Cambridge Lake House.
- Madison/Stoughton 3 BR/3 BA Lake Kegonsa Cottage
- Beautiful White Barnnn
- Lake Kegonsa 1BR Cottage 15 Min.to Madison,Sleeps 3 ,Kayaks
- Beautiful New Glarus, WI Apartment
- Two Bedroom Cottage with Great Lake Views!
- Adorable Updated Cozy Cottage set on Lake Wisconsin's Sunset Bay
- Cozy cabin one block from lake, private beach and close to hiking/biking trails
How much does it cost to rent a place to stay near Madison in the wintertime?
The average cost for winter rentals in Madison is $371 per night. Madisonvacationrental 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.
Are there any winter cottages/chalets in Madison that allow pets?
Yes, here are the top cottage/chalet rentals in Madison that allow you to bring your pet or dog:
- Waterfront Lake Ripley getaway. Kayak, paddleboard and fish from private pier!
- Luxury Prairie Retreat 5 Min from Madison!
- The Buckingham Inn
- Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard
See all pet-friendly vacation rentals in Madison on Madisonvacationrental
Do you have any winter rentals in Madison that are suitable for families?
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.
Are there winter accommodations in Madison that have indoor swimming pools?
As of 2026, the data from Madisonvacationrental shows that there are over 415 private swimming pools or indoor pools accommodations near Madison along with other great amenities.
