Southwest Wisconsin Holidays

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Where to stay in Southwest Wisconsin

Find the best Southwest Wisconsin areas and neighborhoods for the activities you enjoy most. Learn more about Southwest Wisconsin
Madison featuring flowers, a house and a garden

Downtown Madison

The ample dining options and fantastic lake views are top of the list for many visitors to Downtown Madison. A stop by Orpheum Theater or Overture Center for the Arts might round out your trip.

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Top hotels in Southwest Wisconsin

The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
1 W Dayton St, Madison, WI
Fully refundableReserve now, pay when you stay
9.4/10 Exceptional! (3,198 reviews)
"High end cocktails and better selection of high-end wines"

Reviewed on 13 Oct 2025

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The Madison Concourse Hotel and Governor's Club
Baymont by Wyndham Madison West/Middleton WI West

Baymont by Wyndham Madison West/Middleton WI West

2.5 out of 5
8102 Excelsior Dr, Madison, WI
Fully refundableReserve now, pay when you stay
The price is 1.617.738 ₫ per night from 26 Oct to 27 Oct
1.617.738 ₫
1.868.488 ₫ total
26 Oct - 27 Oct
includes taxes & fees
8/10 Very Good! (1,010 reviews)
"Great stay for the price"

Reviewed on 8 Oct 2025

Baymont by Wyndham Madison West/Middleton WI West
Natura Treescape Resort

Natura Treescape Resort

2.5 out of 5
400 County Road A, Wisconsin Dells, WI
8/10 Very Good! (1,112 reviews)
Nice place
"It was very nice, definitely worth what we paid. Not much has been updated recently , but it wasn’t a problem. A solid place, we stayed during off season but it looked like nice outdoor facilities."

Reviewed on 12 Oct 2025

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Natura Treescape Resort
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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.

Popular places to visit

Top Secret

Top Secret

Enjoy a stop at Top Secret, an entertaining place to visit in Wisconsin Dells. Stroll along the riverfront in this family-friendly area or visit its top-notch restaurants.

Top Secret
Capitol Square

Capitol Square

5/5(2 reviews)

You can find out about the history of Madison when you stop by Capitol Square. Visit the area's shops or simply enjoy its restaurants.

Capitol Square

Kalahari Indoor Waterpark

Enjoy the rides and games at Kalahari Indoor Waterpark and see why this is a favourite theme park in Baraboo. Stroll along the riverfront or experience the entertainment choices in this family-friendly area.

Kalahari Indoor Waterpark