Southwest Wisconsin Kid friendly Holidays

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FAQs: family holidays in Southwest Wisconsin

How can I find the best family-friendly holidays in Southwest Wisconsin?

At Expedia, it’s super-easy to find family-friendly holidays in Southwest Wisconsin in our vast inventory. Use our handy filters to find hotels and resorts with the best reviews, most amenities and lowest price tags. You can also hunt out great flights and smashing deals on car hire, so you can book the whole shebang in one place.

Are there any cheap Southwest Wisconsin family holidays?

Avoid forking out for multiple hotel rooms by booking a villa or apartment with a kitchen and give your brood plenty of space and all the meals they love at a fraction of the cost. Find the most affordable family holidays by filtering your search by price. Generally, Southwest Wisconsin family getaways start at . Prices and availability are subject to change and additional terms may apply.

Can I book an all-inclusive Southwest Wisconsin family holiday package?

All-inclusive holidays can keep the costs down when you’re travelling as a family. Think unlimited mocktails for the little'uns and double doses of gin for the bigguns. Use our all-inclusive filter to see what’s available in Southwest Wisconsin and book the whole package in just a few clicks.

How can I book the best family activity holiday in Southwest Wisconsin?

Family holidays are all about spending quality time together, laughing, playing and bonding as you try new things. Pack your trip full of family activities they’ll love and make memories that’ll last a lifetime.

Can I find luxury family holidays in Southwest Wisconsin?

To treat the kids to a luxury holiday they’ll never forget, take a look at the most indulgent hotels and resorts in Southwest Wisconsin by using our 5-star filter. To really travel in style, use the first-class filter to find the best flights, too.

How can I search for Southwest Wisconsin family holiday deals?

Start by entering your dates, then use the family-friendly filter to narrow down your search to show the best available Southwest Wisconsin family holiday deals. If your travel dates are flexible, play around to see if you can find cheaper options or more availability at different times.

Can I book a Southwest Wisconsin family vacation package with free cancellation and/or flexible dates?

Plans change, so booking a family holiday with free cancellation is a great way to ensure you don’t lose out if they do. Use the fully refundable and reserve now pay later filters to find flexibility. Make sure you always check terms and conditions, too.

Why should I book my Southwest Wisconsin family trip with Expedia?

Forget family fights and start thinking about family flights. Our huge selection of easy to browse family-friendly holidays means you can find and book your dream family trip to Southwest Wisconsin in no time.

Top Kid friendly Southwest Wisconsin Hotels

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
Stay at this family-friendly resort in Wisconsin Dells. Enjoy an outdoor pool, free water park access and parking (surcharge). Our guests praise the clean rooms ...
6.8/10 (2,603 reviews)

Families like: Outdoor pool, free water park access, playground, games room

Travellers say...
Not much staff around in the hotel area. Water park lots of staff/lifeguards. One section of water park was closed the 2nd day and

Reviewed on 3 Feb 2026

Mt. Olympus Water & Theme Park Resort
Chula Vista Resort, Trademark Collection by Wyndham

Chula Vista Resort, Trademark Collection by Wyndham

3.5 out of 5
2501 River Rd Wisconsin Dells WI
  • 2 hours drive from University of Wisconsin-Madison
Stay at this spa resort in Wisconsin Dells. Enjoy free Wi-Fi, an outdoor pool and a full-service spa. Popular attractions Chula Vista Waterparks and Mt. Olympus ...
7/10 Good! (1,000 reviews)

Families like: Outdoor pool, free water park access, mini golf, games room

Travellers say...
Clean,excellent customer service

Reviewed on 15 Oct 2025

Chula Vista Resort, Trademark Collection by Wyndham
Tamarack Wisconsin Dells a Ramada by Wyndham

Tamarack Wisconsin Dells a Ramada by Wyndham

3 out of 5
874 Xanadu Rd. Wisconsin Dells WI
  • 2 hours drive from University of Wisconsin-Madison
Stay at this family-friendly holiday home in Wisconsin Dells. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff in their ...
9/10 Wonderful! (973 reviews)

Families like: Outdoor pool, kitchen, playground, games room

Travellers say...
The apartments were nice. Clean. Affordable. Stocked with dishes and cookware. Would stay again.

Reviewed on 1 Jan 2026

Tamarack Wisconsin Dells a Ramada by Wyndham
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.