Travel Back in Time at these Wisconsin Cabins and Hotels

When you escape to a vacation in Wisconsin, you’ll feel a wave of serenity wash over you. Between the refreshing scenery and welcoming residents, you and your traveling companions will wonder if you’ve slipped back into a simpler time. And many of the cabins and hotels here capture this throwback feel. From summer camp nostalgia to neon-sign motels brimming with mid-century flair, you and your group are sure to love the vintage vibes at these destinations that make spending quality time together even sweeter.

Camp Wandawega – Elkhorn

Tucked away in Elkhorn, north of Lake Geneva, Camp Wandawega is a true blast from the past; one can easily sense the history here. Since the 1920s, it’s operated as a hotel, speakeasy, resort and church camp. Today, it’s a stylish homage to summer camps of yore, with cabins, tents and even a treehouse outfitted with the owners’ flea market treasures.

The camp doesn’t mince words when it proclaims itself as rustic (no air conditioning, communal bathrooms) and daytime activities stay true to the summer camp theme: archery, canoeing, swimming, biking and more. At the end of the day, gather around the campfire with your crew for s’mores and stargazing.

Holiday Music Motel – Sturgeon Bay

Feel like the star of your own indie movie by staying in this stylish mid-century motel in Door County. Originally opened in 1952, it was bought and restored by a group of musicians in 2009. Eclectic rooms showcase real-deal 1950s décor, down to the funky furniture and retro curtains.

There’s something else that makes this motel stand out: It’s the world’s only fully operational motel with live music, collaborative songwriting retreats and a radio station exclusively broadcasting the music created within its own walls. Whether you’re a traveling musician or just looking for a unique stay in Sturgeon Bay, the Holiday Music Motel makes for a great launching point for all your group’s adventures.

Maxwell Mansion - Lake Geneva

The charming spirit of Lake Geneva is alive and well at Maxwell Mansion, the first of its kind built on the scenic shore. The renovated historic mansion, carriage house and stables display carefully curated antique décor alongside modern amenities like whirlpool tubs and chromotherapy lighting.

You and your group can play croquet or bocce ball on the lawn for a classy afternoon spent together. Then, head to the property’s libation destinations: The Apothecary Bar, where barkeeps dressed in period clothing serve swanky cocktails and The Speakeasy, an underground bar that requires a password. The covert word is only shared with hotel guests and Facebook followers.

Alderwood Resort – Manitowish Waters

Head North to Manitowish Waters for a true-blue Wisconsin cabin experience. Operating since the 1930s, a cranberry-farming family purchased the Alderwood Resort in 1988 and they’ve been specializing in hospitality ever since. Other than a refresh here and a modern bathroom there, these cabins look virtually unchanged from the ‘30s. 

Enjoy a private dock and explore Alder Lake by rowboat, canoe or kayak (provided to guests). Top off your vintage vacation with fishing, horseshoes and a library of beloved board games that are sure to make for memorable nights spent with family.

Explore Wisconsin's quiet and cozy cabins, or find more charming places to stay with our directory!