Southwest Wisconsin Vacations from $525

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Your Southwest Wisconsin Vacation

Choose a vacation package to Southwest Wisconsin and make planning your adventure a breeze. With all the details arranged before you leave, you can focus on enjoying every second in this destination. A trip to Southwest Wisconsin wouldn't be complete without experiencing some of its best cities, starting with Wisconsin Dells. A couple of the most popular attractions here include Mt. Olympus Water and Theme Park and Chula Vista Waterparks. La Crosse is another favorite city with Southwest Wisconsin travelers. Visitors to this destination enjoy Oktoberfest Grounds and Onalaska Omni Center. From the moment you book your Southwest Wisconsin vacation to when you get back home, Expedia will take care of you every step of the way.

The Latest Southwest Wisconsin vacation packages

Price found within the past 48 hours. Click for updated prices.
Palmer House a Hilton Hotel
Hilton Chicago
theWit Chicago, a Hilton Hotel
Trump International Hotel & Tower Chicago
LondonHouse Chicago, Curio Collection by Hilton
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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

Discover the most popular places to visit in Southwest Wisconsin

Southwest Wisconsin Hotel Deals

Mt. Olympus Water & Theme Park Resort
Mt. Olympus Water & Theme Park Resort
3 out of 5
655 N. Frontage Road, Wisconsin Dells, WI
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $107 total per night from Jul 10 to Jul 11
$107 total
Jul 10 - Jul 11
Total includes taxes and fees
6.6/10 (2,132 reviews)
"Great"

Reviewed on Jul 7, 2025

Mt. Olympus Water & Theme Park Resort
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
$139 nightly
The price is $161 total per night from Jul 27 to Jul 28
$161 total
Jul 27 - Jul 28
Total includes taxes and fees
9.4/10 Exceptional! (2,815 reviews)
Weekend stay
"Very nice older hotel near the Capital and walking distance to all things DT Madison. Rooms are comfortable with great views of the Capital. We enjoyed our stay. The beds are super comfortable and the room was large. Was a bit disappointed I didn't notice there was no microwave in the room. The AC ..."

Reviewed on Jul 7, 2025

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
$69 nightly
The price is $80 total per night from Jul 20 to Jul 21
$80 total
Jul 20 - Jul 21
Total includes taxes and fees
7.8/10 Good! (1,005 reviews)
"Good"

Reviewed on Jul 6, 2025

Baymont by Wyndham Madison West/Middleton WI West
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.

Find the Best Southwest Wisconsin Vacation Packages

Southwest Wisconsin Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Dane County Regional Airport (MSN)

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.