Southwest Wisconsin Ski Holidays 2026

Photo by Inbal Arieh

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Top Ski Southwest Wisconsin Hotels

Days Inn by Wyndham Portage/Cascade Mountain area

North 5781 Kinney Road Portage WI

1 hour drive from University of Wisconsin-Madison

Stay at this business-friendly hotel in Portage. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular ...

Best Western Baraboo Inn

725 W Pine St Baraboo WI

1 hour drive from University of Wisconsin-Madison

Stay at this hotel in Baraboo. Enjoy free breakfast, free parking and room service. Our guests praise the breakfast and the helpful staff in their reviews. Popular ...

8.2/10 Very good! (1,006 reviews)

"It was average ok. On the low side of Best Western standard. Maintained by asian Indians. Indian food smell in the hallway, although the staff has no control over what guests do in their rooms. Carpet replacement renovation was going on, completely blocking both stairwells. No elevator in my half ..."

Reviewed on 21 Sept 2026

Sunset Bay Resort & Suites

921 Canyon Road Wisconsin Dells WI

2 hours drive from University of Wisconsin-Madison

Stay at this beach hotel in Wisconsin Dells. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff and the clean rooms in their ...

8.6/10 Excellent! (894 reviews)

"We enjoyed the resort. Unfortunately it rained all weekend (In September) we enjoyed our visit. Pool was comfortable and we even swam in the outdoor pool til the rain got cold. Other couple we stayed with said bed was uncomfortable but dealt with it. Was nice to have a kitchen and 2 bathrooms. Will ..."

Reviewed on 22 Sept 2026

See all 3,892 properties in Southwest Wisconsin

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.