Southwest Wisconsin Luxury Vacations

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Top Luxury vacation packages in Southwest Wisconsin

Price found within the past 48 hours. Click for updated prices.
The Edgewater
Best Western Premier Park Hotel
The Charmant Hotel
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See all available trips from Columbus to Southwest Wisconsin
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3 Night Luxury vacations in Southwest Wisconsin

Price found within the past 48 hours. Click for updated prices.
Best Western Premier Park Hotel
The Edgewater
The Charmant Hotel
Don't see what you're looking for?
See all available trips from Columbus to Southwest Wisconsin
View all trips

4 Night Luxury vacations in Southwest Wisconsin

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Madison South
The Madison Concourse Hotel and Governor's Club
Days Inn & Suites by Wyndham Madison
Don't see what you're looking for?
See all available trips from Columbus to Southwest Wisconsin
View all trips

All you need to know about luxury vacations in Southwest Wisconsin

What can I expect from a luxury Southwest Wisconsin vacation?

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Southwest Wisconsin vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views. 

How can I find all-inclusive luxury vacation packages in Southwest Wisconsin?

By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5* filter to find truly sensational stays. You barely need to lift a finger. 

Can I book a cheap Southwest Wisconsin luxury vacation?

Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at $512. Prices and availability are subject to change. Additional terms may apply.

How can I book a luxury family vacation in Southwest Wisconsin?

Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi. 

Can I book a package in Southwest Wisconsin with a luxury vacation home?

A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package.   

How can I find the best luxury vacation deals in Southwest Wisconsin?

Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months.

Can I book a luxury holiday in Southwest Wisconsin with free cancellation and/or flexible dates?

Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan. 

Why should I book my luxury trip to Southwest Wisconsin with Expedia?

A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind.

Top Luxury Southwest Wisconsin Hotels

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
  • 5 min drive from University of Wisconsin-Madison
Choose luxury at The Madison Concourse Hotel and Governor's Club, where you can enjoy amenities like plush bedding, premium channels, and more. The indoor pool, ...
9.4/10 Exceptional! (2,987 reviews)
"walking distance from the Capitol building, restaurants, and bars."

Reviewed on Aug 17, 2025

The Madison Concourse Hotel and Governor's Club
The Edgewater

The Edgewater

4.5 out of 5
1001 Wisconsin Place, Madison, WI
  • 4 min drive from University of Wisconsin-Madison
Stay in the lap of luxury at The Edgewater, where you can enjoy amenities like massage services, pillowtop beds, and more. Deluxe amenities at this hotel include ...
9.2/10 Wonderful! (1,001 reviews)

Reviewed on Aug 16, 2025

The Edgewater
Mt. Olympus Water & Theme Park Resort

Mt. Olympus Water & Theme Park Resort

3 out of 5
655 N. Frontage Road, Wisconsin Dells, WI
  • 2 hours drive from University of Wisconsin-Madison
Pamper yourself with a luxe vacation at Mt. Olympus Water & Theme Park Resort. Popular amenities include a lazy river, an outdoor pool, and a restaurant.
6.8/10 (2,323 reviews)
"Convenient."

Reviewed on Aug 15, 2025

Mt. Olympus Water & Theme Park Resort
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.

More vacations you might like

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