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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

Book a stay at this business-friendly hotel in Portage. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...

6.8/10 (1,006 reviews)

Parking lot is awful. The beds were clean. The hotel is in major need of updates. The breakfast did not have many choices.

Reviewed on 2026/5/9

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 our reviews. Popular ...

8.2/10 Very Good! (1,002 reviews)

I had my DoorDash order taken by another guest from outside my room. By the time the staff reviewed the cameras and figured out what room they were in, they had eaten nearly all the food. The hotel did reimburse me back the cost of the DoorDash order. Thank you. 😊

Reviewed on 2026/4/30

Sunset Bay Resort

921 Canyon Road Wisconsin Dells WI

2 hours drive from University of Wisconsin-Madison

Book a stay at this beach hotel in Wisconsin Dells. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...

8.6/10 Excellent! (836 reviews)

I never saw a breakfast menu and the group above us were jumping around all night, the front desk called them but they didn't stop till almost midnight.

Reviewed on 2026/4/21

See all 3,760 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.