Discover winter rentals Madison - We found 396 exact matches
About Madison Winter Rental on Vacation Cottage
At Vacation Cottage, we showcase a diverse array of accommodations in Madison, WI perfect for your winter retreat or seasonal escape. Our listings encompass hotels, private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments, ensuring travelers find their ideal accommodation. Vacation Cottage's winter vacation homes boast premier amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.
Whether you're seeking to escape the snow or embrace it, Vacation Cottage facilitates your connection to the finest cabins, bungalows, lodges, rent-by-owner homes, and the best accommodations in both sunny retreats and ski resorts. Vacation Cottage ensures your winter getaway becomes an unforgettable experience.
Vacation Cottage presents luxury options for travelers seeking to rent a place in Madison. To access these benefits and book your winter vacation home, simply utilize the Vacation Cottage filter option. Enter your travel dates, refine your search with filters for property type and amenities, then choose from our extensive list of exceptional winter vacation rentals hassle-free. Our interactive map further enhances your experience, allowing you to explore destinations worldwide or within Madison and unlock incredible deals. Life is Better at the Cottage with Vacation Cottage.
Frequently Asked Questions About Madison Winter Rentals
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
- A Pleasant Retreat- No Cleaning Fee & New Discounts
- Madison & ~UW~-Madison Area Lakefront Home
- A TOUCH OF COUNTRY LIVING Minutes from Madison
- Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard
- ONE OF A KIND vacation rental with a view
- Conveniently Located just off University Avenue on Madison's West Side
- Original cozy farmhouse homestead 2 blocks from the bike path and
- Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
- Rustic Luxury Awaits In This Beautiful Full Log Lodge On 44 Private Acres
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 $372 per night. Vacation Cottage 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:
- ‘Happy’s Haven’ Cabin w/Gas Grill & Fire Pit!
- Luxury Prairie Retreat 5 Min from Madison!
- The Buckingham Inn
- Beautiful New Glarus, WI Apartment
See all pet-friendly vacation rentals in Madison on Vacation Cottage
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 2025, the data from Vacation Cottage shows that there are over 396 private swimming pools or indoor pools accommodations near Madison along with other great amenities.
Do any winter holiday rentals in Madison have hot tubs?
About 396 holiday rentals in Madison boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Madison?
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.
