When the snow starts to fall and holiday lights begin to glow, Wisconsin becomes a wonderland of comfy getaways, scenic adventures, and memory-making moments. Whether you’re planning a quick weekend trip or a winter break getaway, Sheboygan, Elkhorn, and Baraboo offer the perfect mix of comfort, connection, and family fun.

Sheboygan

Cozy Coastal Charm on Lake Michigan

When winter paints the lakeshore in silver and white, Sheboygan transforms into a coastal retreat full of warmth and wonder. Known as the “Malibu of the Midwest,” this lakeside gem blends relaxation with a dash of adventure. 

STAY

With Great Lakes Getaways, families can choose from an array of beachfront condos and villas featuring all the comforts of home. From Breezy Beach and Indigo Waters to Perfect Paradise, each property captures the charm of lakeside living. Think sunrise over the lake, warming up in front of a fire, waves as your soundtrack, and easy access to the best of Sheboygan. Book your stay at StayWithGLG.com. Save 10% on any stay with code TGVG10. Plus, earn discounts on future stays.

PLAY

Bundle up and explore the city’s offerings. Visit the Above & Beyond Children’s Museum for hands-on fun, or head outdoors to DeLand Park or Kohler-Andrae State Park for peaceful lake views, snowy walks, and plenty of photo-worthy moments. Families also love the Shaw Family Playground and the charming South Pier District, where shops and eateries stay lively all season.

EAT

Warm up with comfort classics – breakfast at Field to Fork, BBQ and pizza at Parker John’s, or hearty family meals at Parkside Family Restaurant. And for a sweet stop that kids will love, head to South Pier Parlor for hand-dipped ice cream and fun, old-fashioned treats. Whether it’s a hot cocoa by the lake or dinner with a view, Sheboygan makes cozy feel easy.

Elkhorn

Small-Town Magic in the Heart of Winter

If you’re dreaming of a holiday straight from a snow-globe, Elkhorn is your perfect match. This friendly Walworth County town shines in winter with its festive markets, dining, and family-friendly outdoor fun.

STAY

Elkhorn offers everything from charming Airbnbs to welcoming hotels and resorts with convenient locations to all the winter fun in Elkhorn. The Holiday Inn is a local favorite – spacious rooms, a warm atmosphere, and a pancake conveyor belt that kids can’t resist.

PLAY

From the slopes of Alpine Valley Resort to ice fishing, sledding, and cross-country skiing around town, there’s fun for every pace. December brings the magic of Elkhorn’s Winter Markets, including the Apple Barn Orchard & Winery, Terra Barn Collective, and Uncle Hunk’s Junk Building. At Duesterbeck Brewing Co. families can enjoy an afternoon of board games by the fire.

EAT

Stop by Mama T’s Italian Eatery for a home-style meal made from scratch, with recipes passed down through generations – the kind that makes everyone feel right at home. Savor Someplace Else’s plate-sized pot pies (and their new colorful mural), or pop into Friends on the Square for hot cocoa or ice cream. It’s the kind of small-town hospitality that keeps families coming back.

Baraboo

History, Theatre & Winter Beauty in the Bluffs

Just 20 minutes from Wisconsin Dells, Baraboo is a storybook winter escape where history meets natural beauty. With its circus heritage, vibrant arts scene, and scenic bluffs, it’s a destination that feels both timeless and fresh.

STAY

Rest where history lives at the Ringling House Bed & Breakfast, once home to one of the famous Ringling Brothers, or take in sweeping views from the Inn at Wawanissee Point. Great Lakes Getaways also offers nearby short-term rental condos in Wisconsin Dells – spacious, modern, and perfect for gathering loved ones. Book your stay at staywithglg.com and save 10% on any stay with code TGVG10.

PLAY

Hit the slopes at Devil’s Head Resort or hike through Devil’s Lake State Park for breathtaking winter scenery. Even under a blanket of snow, Devil’s Lake is a sight to behold. Perfect for family photos, and taking in the quiet beauty of winter in the bluffs. Catch a performance or tour at the beautifully restored Al. Ringling Theatre, and watch for upcoming Winter Quarters events celebrating Baraboo’s legendary circus roots. 

EAT

Baraboo’s food scene is full of flavor and heart. The inviting Little Village Café serves classic American dishes inside a charming 1940s diner. On the east side, the Log Cabin offers rustic warmth with breakfast served all day and signature homemade pie that’s worth the trip on its own. And for an elevated experience, Driftless Glen Distillery pairs fine dining with handcrafted local spirits.

Plan Your Winter Escape

Whether it’s the lakeshore calm of Sheboygan, the hometown cheer of Elkhorn, or the historic magic of Baraboo, Wisconsin offers families endless ways to reconnect this season. Pack your mittens, curl up by the fire, and get ready to make this winter one to remember.