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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. ...

6.6/10 (1,000 reviews)

The pool room was very clean and had towels at all times. We brought our own bedding and housekeeping made our bed with our bedding. Staff was very kind and respectful.

Reviewed on 2026/1/4

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)

Great location, nice rooms, and friendly staff

Reviewed on 2026/1/9

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 an outdoor pool, a private beach, and a sauna. Our guests praise the helpful staff and the clean rooms ...

8.6/10 Excellent! (823 reviews)

Excelente

Reviewed on 2026/1/3

See all 3,700 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.