Southwest Wisconsin Romantic Holidays 2026

Photo by Inbal Arieh

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Top Romantic Southwest Wisconsin Hotels

Ho-Chunk Casino Hotel - Wisconsin Dells

S3214 County Road BD Baraboo WI

1 hour drive from University of Wisconsin-Madison

Stay at this business-friendly hotel in Baraboo. Enjoy free Wi-Fi, free parking and a casino. Popular attractions Kalahari Indoor Waterpark and Noah's Ark Waterpark ...

Caribbean Club Resort

1093 Canyon Road Wisconsin Dells WI

2 hours drive from University of Wisconsin-Madison

Stay at this beach condo in Wisconsin Dells. Enjoy an outdoor pool, a private beach and a sauna. Our guests praise the pool and the property condition in their ...

8/10 Very good! (381 reviews)

"Our party of five slept comfortably in this cute condo. It was right on a small beach on the lake. Although it rained the entire time, and geese filled the beach and dock area, we didn’t spend any time in the water. I am sure in beautiful weather, it is an absolute gem on the beach. Pool and hot ..."

Reviewed on 24 Sept 2026

Great Wolf Lodge Wisconsin Dells

1400 Great Wolf Dr Baraboo WI

2 hours drive from University of Wisconsin-Madison

Stay at this family-friendly resort in Baraboo. Enjoy free Wi-Fi, 6 indoor pools and 3 restaurants. Our guests praise the helpful staff in their reviews. Popular ...

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.