
Southwest Wisconsin Ski Vacations
Book a Ski Hotel + Flight or Car together to unlock savings
4 Night Ski vacations in Southwest Wisconsin

GrandStay Hotel & Suites
Reviewed on Oct 24, 2025


Days Inn & Suites by Wyndham Madison
Reviewed on Oct 4, 2025
Planning your Southwest Wisconsin ski vacation
What are some things I should consider when booking a Southwest Wisconsin ski trip package?
Yes, you want pristine powder and perfect runs, but take a moment to consider how close you want to be to the slopes, what extras you want from your resort, and—of course—how much après ski you intend to indulge in.
How can I find cheap Southwest Wisconsin ski packages?
Fly down the slopes during low or shoulder season, either side of , for a ski package to please your purse. Right now, ski trips start at just $325. Prices and availability are subject to change. Additional terms may apply.
Can I book a beginner ski package in Southwest Wisconsin?
Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in Southwest Wisconsin. Book lessons so you can gear up to take on the rest of the mountain with confidence. Après awaits for all after an eventful day in the snow.
How much does a ski trip to Southwest Wisconsin cost?
Sensational ski trips to Southwest Wisconsin start from $325. Use the budget filter to find powder at your perfect price. As always, prices and availability are subject to change. Additional terms may apply.
When’s the best time of year to plan a ski trip to Southwest Wisconsin?
The best time to hit the slopes in Southwest Wisconsin depends on what you’re looking for. If you’re all about powder-packed pistes and brilliant blue-sky skiing conditions, aim for the middle of the season. Alternatively, if you’re willing to take a chance on start or end of season snow, you’ll bag much cheaper prices —just make sure there’s a spa or après bar to shelter in on white-out days.
Can I book Southwest Wisconsin ski packages with airfare?
Save money on your snow time by booking your accommodation, airfare, and car rental in a brilliant bundle. It’s both convenient and cash-flow friendly.
Can I book a Southwest Wisconsin ski trip with free cancellation and/or flexible dates?
Flexibility is always a bonus when you’re flying down the slopes—and it makes for an easier booking process, too. Check the payment option filter to find trips with free cancellation as well as buy now, pay later options.
Why should I book a ski package in Southwest Wisconsin with Expedia?
Simple search and fantastic filters make it easy to find, build, and book your dream Southwest Wisconsin ski vacation in just a few clicks. It’s ‘snow’ joke, it really is that easy.
Top Ski Southwest Wisconsin Hotels

Days Inn by Wyndham Portage/Cascade Mountain area
Nice
Reviewed on Sep 22, 2025

Best Western Baraboo Inn
Overall an above average motel
Reviewed on Oct 20, 2025

Sunset Bay Resort
Great stay love the lake and kayaks included Beds a little hard but always a great time visit yearly
Reviewed on Oct 19, 2025


















