Southwest Wisconsin Vacations

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  • Plan, book, travel with confidence

  • Better together

    Save up to ₩1,660,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, book, and manage your trip all in one place

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
A large domed building surrounded by modern cityscape and a body of water.

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

Find the Best Southwest Wisconsin Vacation Packages

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
The price is ₩145,308 per night from Aug 4 to Aug 5
₩145,308
₩163,099 total
Aug 4 - Aug 5
includes taxes & fees
7/10 Good! (2,820 reviews)
"Nice enough room. I enjoyed staying at Hotel Rome over the other site. Our bracelets won't work to get in and out of bldg and rooms. They gave us cards instead. Indoor Waterpark was not open, that truly sucked. It was a good vacation. Those issues really aren't a deterent. We will probably be ..."

Reviewed on Jul 3, 2026

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
The price is ₩180,736 per night from Jul 5 to Jul 6
₩180,736
₩208,750 total
Jul 5 - Jul 6
includes taxes & fees
9.4/10 Exceptional! (3,927 reviews)
"very nice"

Reviewed on Jul 3, 2026

The Madison Concourse Hotel and Governor's Club
Dellshire Resort

Dellshire Resort

3.5 out of 5
2277 Wisconsin Dells Pkwy Wisconsin Dells WI
The price is ₩260,129 per night from Jul 9 to Jul 10
₩260,129
₩343,516 total
Jul 9 - Jul 10
includes taxes & fees
8.8/10 Excellent! (104 reviews)
"The theming was amazing! We loved the music that played through the resort and all of the decor. We thought the amenities- arcade, pool, fitness center, etc- were all awesome and the room was spacious and comfortable. The food was to die for! Every staff member that we met was helpful, friendly, ..."

Reviewed on Jul 4, 2026

Dellshire Resort
See all 3,838 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.

Stay near popular Southwest Wisconsin attractions

A water park with a large Ferris wheel and a water slide.

Mt. Olympus Water and Theme Park

7.4/10 (1,284 reviews)
Enjoy the rides and games at Mt. Olympus Water and Theme Park and see why this is a favorite amusement park in Wisconsin Dells. Stroll along the area's lakeside or experience its entertainment choices.
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Frequently asked questions

How much does a Southwest Wisconsin vacation 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 vacation 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 1,000,000 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 travelers.
How far in advance should I book my Southwest Wisconsin vacation?
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 travelers 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 organizing a luxury city stay with your love or an affordable family break, check out our vacation packages today.
Can I choose my airline with a Southwest Wisconsin Expedia vacation package?
You can. We have more than 550 partner airlines globally, so go with the carrier that matches your budget and traveling style.
If I'm not able to travel, can I cancel my Southwest Wisconsin vacation 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.

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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.