Southeast Wisconsin Ski Holidays

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Planning your Southeast Wisconsin ski holiday

How can I book the best ski holiday to Southeast Wisconsin in 2025/2026?

Search through alpine adventures on Expedia to plan your perfect snowy ski holiday in Southeast 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 Southeast Wisconsin ski holidays?

Boot hire, lift passes, lessons: ski holidays can get pricey, quickly. To make your ski trip more affordable, book Southeast 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 Southeast Wisconsin?

Use our handy last-minute deals page to look for ski holidays to Southeast 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 Southeast Wisconsin?

Southeast 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 Southeast Wisconsin?

All-inclusive ski holidays are fairly rare, but you can use our filter to see if there are any available in Southeast 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 Southeast Wisconsin?

Ski season in Southeast 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 Southeast 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 Southeast 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 Southeast Wisconsin that offer it.

Why should I book a ski holiday package in Southeast 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 Southeast Wisconsin Hotels

Grand Geneva Resort & Spa

Grand Geneva Resort & Spa

4 out of 5
7036 Grand Geneva Wy, Lake Geneva, WI
  • 1 hour drive from American Family Field
Stay at this 4-star spa resort in Lake Geneva. Enjoy free Wi-Fi, free parking and a full-service spa. Our guests praise the helpful staff in their reviews. Popular ...
8.4/10 Very Good! (1,001 reviews)
"Good facility options"

Reviewed on 17 Aug 2025

Grand Geneva Resort & Spa
Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

3.5 out of 5
7020 Grand Geneva Way, Lake Geneva, WI
  • 1 hour drive from American Family Field
Stay at this 3.5-star spa aparthotel in Lake Geneva. Enjoy free parking, an outdoor pool and a full-service spa. Our guests praise the helpful staff and the ...
8.6/10 Excellent! (2,955 reviews)
"Loved it all"

Reviewed on 18 Aug 2025

Timber Ridge Lodge and Waterpark
Holiday Inn Club Vacations at Lake Geneva Resort by IHG

Holiday Inn Club Vacations at Lake Geneva Resort by IHG

3.5 out of 5
7036 Grand Geneva Way, Lake Geneva, WI
  • 1 hour drive from American Family Field
Stay at this 3.5-star spa resort in Lake Geneva. Enjoy free parking, an outdoor pool and a full-service spa. Our guests praise the helpful staff in their reviews. ...
8.6/10 Excellent! (999 reviews)
Wonderful stay!
"I was attending a retreat at the Grand Geneva Resort, which was a 3 minute drive away. I could have walked about 20 minutes or requested shuttle service from my room to the meeting room at the resort, but I was glad to have a rental car. I enjoyed walking for exercise and fun around the spectacularly ..."

Reviewed on 19 Aug 2025

Holiday Inn Club Vacations at Lake Geneva Resort by IHG
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.

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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. Flight-inclusive packages are ATOL protected.