Southwest Wisconsin Holidays

Book a Hotel + Flight or Car together to unlock savings

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! (2,724 reviews)
"Love this hotel! Stay here every time we visit our kids in college in Madison!"

Reviewed on 21 Jun 2025

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The Madison Concourse Hotel and Governor's Club
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
The price is 914.324 ₫ per night from 24 Jun to 25 Jun
914.324 ₫
2.785.827 ₫ total
24 Jun - 25 Jun
includes taxes & fees
6.6/10 (2,062 reviews)
"Very bad experience. I registered vis Expedia but they charged extra than booking. Not good rooms conditions, no WIFI facility available. Very bad staff at check-in"

Reviewed on 19 Jun 2025

Mt. Olympus Water & Theme Park Resort
Natura Treescape Resort
Natura Treescape Resort
2.5 out of 5
400 County Road A, Wisconsin Dells, WI
8/10 Very Good! (1,064 reviews)
Great fun for families!
"We loved all the activities that were included with the stay! We swam in the indoor pool the night we arrived and went to the water park the next day. Everything was included and aside from paying $2 for grippy socks for our kids we didn't have any extra expenses. The room was comfortable and our ..."

Reviewed on 18 Jun 2025

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Natura Treescape Resort
See all 3,753 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.

Frequently asked questions

How much does a Southwest Wisconsin holiday package cost?
Starting from an incredible , you can handcraft your own Southwest Wisconsin package. Simply bundle flights, hotels and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Southwest Wisconsin?
If you love scoring a bargain, bundle your bookings into a Southwest Wisconsin holiday package. Whether you're looking for hotels, flights, activities or rental cars, you can browse and book them all in one place. You'll have lots of choice at your fingertips too. Expedia has over 550 air carriers and 1null000null000 hotel options globally to pick from. Fly with who you prefer, book a room where you like and save a tidy sum --- now that's the ideal escape!
What are the top hotels in Southwest Wisconsin?
Chula Vista Resort, Trademark Collection by Wyndham and Adams Inn know how to make their guests feel at home in Wisconsin Dells. If your travel plans also include Baraboo, check out La Quinta Inn & Ste by Wyndham Wisconsin Dells- Lake Delton and Days Inn & Suites by Wyndham Wisconsin Dells. Both are popular with travellers.
How far in advance should I book my Southwest Wisconsin holiday?
It all depends on the airline, but you can usually look up international fares on Expedia up to 12 months in advance. While it's generally a good idea to book ahead of time, lucky travellers occasionally score a cheaper flight just weeks prior to the date of departure.
What does an Expedia Southwest Wisconsin travel package include?
Travel packages include hotels, rental cars and flights, but you can combine any of them to create your ideal Southwest Wisconsin getaway. You can also add on a few tours and activities once you've made your booking. You're in control! When you combine your bookings with Expedia, you'll score deals you won't find elsewhere.
What should I know before booking a Southwest Wisconsin travel package?
You'll pick up impressive savings when you combine your hotels, flights and rental cars into a package. Plus, booking everything together will make your trip planning easier. So why waste your time or money? Whether you're organising a luxury city stay with your love or an affordable family break, check out our holiday packages today.
Can I choose my airline with a Southwest Wisconsin Expedia holiday package?
You can. We have more than 550 partner airlines globally, so go with the carrier that matches your budget and travelling style.
If I'm not able to travel, can I cancel my Southwest Wisconsin holiday package?
Yes, it's possible to cancel your Southwest Wisconsin booking if your travel plans have changed. Whether you'll be charged a fee or not depends on your airline, hotel or car rental company. It may be possible to cancel or change your booking for free if you booked in the last 24 hours. Visit our Customer Service Portal for more information.

Popular places to visit

Devil's Lake State Park

Devil's Lake State Park

Explore the great outdoors at Devil's Lake State Park, a lovely green space in Wisconsin Dells. Stroll along the lakeside or visit the fun-filled water parks in this family-friendly area.

Devil's Lake State Park
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
Monona Terrace Community and Convention Center

Monona Terrace Community and Convention Center

Learn about the events happening in Monona Terrace Community and Convention Center during your trip to Madison. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Monona Terrace Community and Convention Center