Holidays in the Dells: A Wisconsin Dells Family Vacation for Young Kids

A Wisconsin Dells family vacation during the holidays can feel like a gamble—weather, crowds, energy levels, budgets. You want fun, but not chaos. Memorable, but not exhausting. Festive, but still affordable.

Our recent holiday trip to the Dells checked all those boxes—and then surprised us in the best way. Between our stay at Kalahari Waterpark Resort, a cozy afternoon at Legacy Dinner Theater, and several budget-friendly activities perfect for little ones, this trip was a great way for our family to enjoy a brief getaway.

Here’s how it came together and our top tips for recreating a special holiday experience in dells for your family!

A Resort Stay That Simplifies the Whole Trip

Staying at Kalahari Waterpark Resort with Young Kids

For families traveling with young children, staying somewhere that doubles as entertainment helps reduce stress since you aren’t trying to keep kids busy at the hotel or rental. 

What made it work for us:

• Indoor waterpark access included with your stay (which is especially great during colder months!)

• Designated toddler and young-kid play areas

• On-site dining so you don’t have to load up the kids for every meal

Helpful travel items we packed:

• Waterproof phone pouch for pool days 

• Kids water shoes for slippery surfaces 

An Easy, Sit-Down Experience Everyone Enjoyed

Legacy Dinner Theater: A Special Meal Together

Legacy Dinner Theater was one of the highlights of our Wisconsin Dells family vacation, especially during the holidays.

Here’s what to look forward to:

• Dinner and entertainment in one place

• Kid-friendly storytelling without overstimulation

• A chance for parents to sit and enjoy the evening

After full days of waterpark fun, this was the perfect change of pace—festive, cozy, and surprisingly engaging for younger kids.

Parent tip: Bring a quiet activity for little hands just in case:

• Reusable sticker books

• LCD drawing tablets for mess-free doodling

Budget-Friendly Things to Do in Wisconsin Dells with Kids

Things to Do in Wisconsin Dells Besides Waterparks

The Dells isn’t just about big-ticket attractions. Some of the best experiences—especially with young kids—are affordable or even free.

Our favorite budget-friendly stops:

• Mirror Lake State Park – Easy trails, scenic views, and space for kids to explore

• Downtown Wisconsin Dells – Candy shops, train displays, and slow strolling

• Wizard Quest (short sessions) – Interactive fun without committing to hours

• Seasonal light displays during the holidays

These breaks gave us variety without adding pressure or lots of extra cost.

A Simple Holiday Itinerary for the Wisconsin Dells with Young Kids

Here’s how our Wisconsin Dells family vacation naturally unfolded. This pacing kept days flexible and avoided the rushed, overtired feeling that can sneak up on trips with young kids.

Day 1: Arrival + Waterpark Time

• Arrive at Kalahari Waterpark Resort

• Get settled and head straight to the indoor waterpark

• Keep it low-key the first day, and explore the resort

• Dinner on-site or takeout nearby

After travel, staying close to the room made transitions easy and kept everyone relaxed.

Helpful to have on hand:

• Change of clothes in a lightweight backpack

• Waterproof phone pouch for pool time

Day 2: Waterpark Morning + Legacy Dinner Theater

• Morning swim while energy is high

• Lunch at the resort or back in the room

• Afternoon rest or quiet play (or even a late checkout from the resort if you prefer just a one night stay in the dells)

• Afternoon or Evening at Legacy Dinner Theater

This day balanced movement with downtime and gave us a shared evening experience without juggling multiple plans.

Quiet-time essentials we packed:

• Reusable sticker books 

• LCD drawing tablets for downtime

Day 3 (Optional): Explore the Dells + Budget-Friendly Stops

• Breakfast at the hotel

• Short walk around Mirror Lake State Park

• Walk through downtown Wisconsin Dells

• Seasonal attractions or holiday lights if available

This day stayed flexible. We picked one or two stops and left room to adjust based on moods and weather.

Nice-to-have items:

• Compact stroller

• Spill-proof snack containers while away from the resort 

Day 4 (Optional): One Last Swim + Head Home

• Quick morning swim or pack up

• Check out and head home

Packing Smarter Makes the Trip Easier

Before trips like this, I always pack with comfort and flexibility in mind.

Travel essentials we rely on:

• Kids travel backpacks with snack compartments

• Spill-proof snack containers for hotel rooms and car rides 

• Compact stroller 

These small choices reduce friction—and that’s what turns a trip into a good memory.

The Wisconsin Dells Works for Family Holidays

The Dells is a great choice during the holidays because it’s:

• Drivable for Midwest families

• Offers a variety of indoor activities

• Flexible for different budgets

If you’re looking for a family trip that feels festive without being overwhelming, this destination is a great choice.

Happy Holidays!

Jess