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.

Find hotels in Downtown Madison

Top hotels in Southwest Wisconsin

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 1.185.756 ₫ per night from 2 Sept to 3 Sept
1.185.756 ₫
1.330.714 ₫ total
2 Sept - 3 Sept
includes taxes & fees
6.8/10 (2,361 reviews)
"Li"

Reviewed on 26 Aug 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
Fully refundableReserve now, pay when you stay
9.4/10 Exceptional! (3,023 reviews)
"I loved the bed"

Reviewed on 26 Aug 2025

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The Madison Concourse Hotel and Governor's Club
Days Inn & Suites by Wyndham Wisconsin Dells

Days Inn & Suites by Wyndham Wisconsin Dells

2.5 out of 5
2504 Wisconsin Dells Parkway, Wisconsin Dells, WI
Fully refundableReserve now, pay when you stay
The price is 1.277.433 ₫ per night from 15 Sept to 16 Sept
1.277.433 ₫
1.433.918 ₫ total
15 Sept - 16 Sept
includes taxes & fees
7/10 Good! (1,516 reviews)
"Easy access"

Reviewed on 23 Aug 2025

Days Inn & Suites by Wyndham Wisconsin Dells
See all 3,791 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.

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 lakeside or experience the entertainment choices in this family-friendly area.

Kalahari Indoor Waterpark

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.