Discover winter rentals Upson - We found 75 exact matches
About Upson Winter Rental on Vacation Cottage
At Vacation Cottage, we showcase a diverse array of accommodations in Upson, 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 Upson. 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 Upson and unlock incredible deals. Life is Better at the Cottage with Vacation Cottage.
Frequently Asked Questions About Upson Winter Rentals
What are the top rated Winter Rentals in Upson?
There are a lot of options in Upson. If you plan on staying in the Upson area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Upson:
- Beautiful Riverside Property!
- Authenic Amish built log cabin on 3,300 acre Gile Flowage. All Modern Amenities
- Beautiful Farmhouse on 80 Picturesque Acres
- Eagle Point Cabin on Island Lake in Iron County, Wisconsin
- Close to Hurley, Trail access, near The Gile Flowage with Central Air & King Bed
- Beautiful lake home at a private camp
- Mineshaft Chalets Side #1
- House 2 - Gorgeous A Frame
- Ski-in ski-out 3 Bdrm Chalet w sauna on slopes & lake - Sleeps 8
- Grandpa Jim's Cabin - Close to The Gile Flowage/On ATV Route
How much does it cost to rent a place to stay near Upson in the wintertime?
The average cost for winter rentals in Upson is $298 per night. Vacation Cottage has a wide list of great winter places to stay near Upson that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Upson that allow pets?
Yes, here are the top cottage/chalet rentals in Upson that allow you to bring your pet or dog:
- Beautiful lake home at a private camp
- The Lakeside Eagle's Nest Near the Trail
- Davos Chalet
- Grandpa Jim's Cabin - Close to The Gile Flowage/On ATV Route
See all pet-friendly vacation rentals in Upson on Vacation Cottage
Do you have any winter rentals in Upson that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Upson to find what works for you.
Are there winter accommodations in Upson that have indoor swimming pools?
As of 2025, the data from Vacation Cottage shows that there are over 75 private swimming pools or indoor pools accommodations near Upson along with other great amenities.
Do any winter holiday rentals in Upson have hot tubs?
About 75 holiday rentals in Upson boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Upson?
Yes, there are many luxury places to stay in Upson for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Upson with all the best amenities for your next trip.
