Title: Southwest Wisconsin Ski Holidays 2026 | Expedia.co.uk ![](https://images.trvl-media.com/place/5957/f96cbf4a-3a46-4cf7-b7f2-0fff893f2f53.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Southwest Wisconsin Ski Holidays ## Book a Ski Hotel + Flight or Car together to unlock savings Photo by Inbal Arieh - ## Plan, book, travel with confidence - ### Better together Save up to £335 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 - ### Rest easy Packages with flights are ATOL protected ## Planning your Southwest Wisconsin ski holiday #### How can I book the best ski holiday to Southwest Wisconsin in 2026/2026? Search through alpine adventures on Expedia to plan your perfect snowy ski holiday in Southwest Wisconsin. Just choose your dates and see what’s available. You might prefer a hotel with a heated outdoor pool, or a private chalet for après ski parties; either way, use the property filters to your ideal match. If ski-in-ski-out is important, use the map view to find those idyllic slopeside properties. #### How can I find cheap Southwest Wisconsin ski holidays? Boot hire, lift passes, lessons: ski holidays can get pricey, quickly. To make your ski trip more affordable, book Southwest Wisconsin accommodation a little further from the lifts and go self-catering to cut back on eating out. Sort your search results by price to find options from . Prices and availability are subject to change. Additional terms may apply. #### Can I book last-minute ski holidays to Southwest Wisconsin? Use our handy last-minute deals page to look for ski holidays to Southwest Wisconsin at a steal. If your dates are fixed, simply input the details and see what specials are available. #### What should I consider when booking family ski holidays in Southwest Wisconsin? Southwest Wisconsin is well set up for kids. For the teeniest ski-woks, day care in the snow is a blast. As they get older, they love whizzing around on the hill in ski school. Choose a hotel near the lifts and nursery slopes to save a whole lot of ski-carrying hassle in the mornings. With all that extra time and energy, you can take your sweet time to find a family-favourite bolthole on the mountain for hot chocolate with marshmallows ski breaks. #### Can I book all-inclusive ski holidays to Southwest Wisconsin? All-inclusive ski holidays are fairly rare, but you can use our filter to see if there are any available in Southwest Wisconsin. If not, consider booking your flights and accommodation together to save money that way instead. #### When's the best time of year to plan a ski trip to Southwest Wisconsin? Ski season in Southwest Wisconsin generally starts around December and slopes off around April. Keep an eye on the snow forecasts though, as you can often find some brilliant deals at the start or end of the season, when it’s also much quieter. #### How can I find the best deals on Southwest Wisconsin ski holiday packages? If you can be flexible with your ski holiday dates, avoid school holidays and instead buckle up your boots at the start or end of season. Sort your search results by price and look out for self-catered accommodation to save on notoriously expensive ski-resort drinking and dining. #### Can I book a Southwest Wisconsin ski trip with free cancellation and/or flexible dates? If you’re not 100% sure on plans or just want peace of mind, choose a ski holiday with free cancellation. You can use our free cancellation filter to find properties in Southwest Wisconsin that offer it. #### Why should I book a ski holiday package in Southwest Wisconsin with Expedia? Schuss your way to the slopes with Expedia’s smooth booking process. From flights to hotels and even car hire, you’ll find everything you need to plan the ultimate winter wonderland ski holiday. ## Top Ski Southwest Wisconsin Hotels ![Days Inn by Wyndham Portage/Cascade Mountain area](https://images.trvl-media.com/lodging/1000000/10000/5600/5519/b3ece239_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Days Inn by Wyndham Portage/Cascade Mountain area North 5781 Kinney Road Portage WI - 1 hour drive from University of Wisconsin-Madison Stay at this business-friendly hotel in Portage. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular ... 6.6/10 (1,000 reviews) Great service Reviewed on 2 Dec 2025 [](https://expedia.co.uk/Wisconsin-Dells-Hotels-Days-Inn-By-Wyndham-Portage.h5519.Hotel-Information) ![Best Western Baraboo Inn](https://images.trvl-media.com/lodging/1000000/10000/7800/7724/ca5615e6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Baraboo Inn 725 W Pine St Baraboo WI - 1 hour drive from University of Wisconsin-Madison Stay at this hotel in Baraboo. Enjoy free breakfast, free parking and room service. Our guests praise the breakfast and the helpful staff in their reviews. Popular ... 8.2/10 Very Good! (1,001 reviews) Staff was very nice. Good breakfast Reviewed on 30 Nov 2025 [](https://expedia.co.uk/Wisconsin-Dells-Hotels-Best-Western-Baraboo-Inn.h7724.Hotel-Information) ![Sunset Bay Resort](https://images.trvl-media.com/lodging/2000000/1060000/1051100/1051099/6e8298f6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sunset Bay Resort 921 Canyon Road Wisconsin Dells WI - 2 hours drive from University of Wisconsin-Madison Stay at this beach hotel in Wisconsin Dells. Enjoy an outdoor pool, a private beach and a sauna. Our guests praise the helpful staff and the clean rooms in their ... 8.6/10 Excellent! (819 reviews) Amazing stay Reviewed on 13 Nov 2025 [](https://expedia.co.uk/Wisconsin-Dells-Hotels-Bakers-Sunset-Bay-Resort.h1051099.Hotel-Information) [See all 3,690 properties in Southwest Wisconsin](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=6059824) 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 holidays you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Holidays [](https://expedia.co.uk/lp/theme-holidays/all-inclusive-holidays?rfrr=editorial.All_Inclusive%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Holidays [](https://expedia.co.uk/lp/theme-holidays/beach-holidays?rfrr=editorial.Beach_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/kid-friendly-holidays?rfrr=editorial.Family_Friendly%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Holidays [](https://expedia.co.uk/lp/theme-holidays/golf-holidays?rfrr=editorial.Golf_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Holidays [](https://expedia.co.uk/lp/theme-holidays/luxury-holidays?rfrr=editorial.Luxury_Holidays.click) ![gay friendly holiday packages](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ+ Holidays [](https://expedia.co.uk/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ+_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Holidays [](https://expedia.co.uk/lp/theme-holidays/romantic-holidays?rfrr=editorial.Romantic_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Holidays [](https://expedia.co.uk/lp/theme-holidays/ski-holidays?rfrr=editorial.Ski_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/22/hero-image-pet-friendly_copy.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Pet Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/pet-friendly-holidays?rfrr=editorial.Pet_Friendly%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.co.uk/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ### Top Ski Holiday Destinations > - [Ski Holidays in Andorra ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/4/Andorra) > - [Ski Holidays in Austria ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/11/Austria) > - [Ski Holidays in Borovets ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/602265/Borovets) > - [Ski Holidays in Bulgaria ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/26/Bulgaria) > - [Ski Holidays in Canada ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/31/Canada) > - [Ski Holidays in Chamonix ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/6050949/Chamonix-Mont-Blanc) > - [Ski Holidays in Finland ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/58/Finland) > - [Ski Holidays in France ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/59/France) > - [Ski Holidays in Italy ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/86/Italy) > - [Ski Holidays in Japan ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/89/Japan) > - [Ski Holidays in Meribel ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/8725/Meribel) > - [Ski Holidays in Norway ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/138/Norway) > - [Ski Holidays in Poland ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/146/Poland) > - [Ski Holidays in Scotland ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/11219/Scotland) > - [Ski Holidays in St-Anton ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/5828/Sankt-Anton-Am-Arlberg) > - [Ski Holidays in Sweden ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/173/Sweden) > - [Ski Holidays in Switzerland ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/174/Switzerland) > - [Ski Holidays in Tignes ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/184273/Tignes) > - [Ski Holidays in Val-D'isere ](https://www.expedia.co.uk/lp/theme-holidays/ski-holidays/10259/Val-DIsere) ## More Holiday Ideas [Flights to Southwest Wisconsin ](https://expedia.co.uk/Cheap-Flights-To-Southwest-Wisconsin.d6059824.Travel-Guide-Flights)[ Southwest Wisconsin Hotels ](https://expedia.co.uk/Southwest-Wisconsin-Hotels.d6059824.Travel-Guide-Hotels)[ Southwest Wisconsin Holiday Rentals ](https://expedia.co.uk/Southwest-Wisconsin-Holiday-Rentals.d6059824.Travel-Guide-HolidayRentals)[ Southwest Wisconsin Car Hire ](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Southwest-Wisconsin.d6059824.Car-Hire-Guide)[ Southwest Wisconsin Holidays ](https://expedia.co.uk/Southwest-Wisconsin.d6059824.Holidays-City-Breaks) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app