4 of the Quirkiest Places to Stay in Wisconsin

4 of the Quirkiest Places to Stay in Wisconsin

Your itinerary can be conventional when your lodgings look like this.

Staying at a cabin at the edge of a placid lake or scenic bluff is not that difficult in the Dairy State. But what about waking up in a hobbit-style hut or a decommissioned warbird? Inject some weirdness into your otherwise conventional travel by resting your head in one of these lodgings.


READ MORE FROM OUR “WEIRD WISCONSIN” FEATURE HERE.


It’s time to pick your Milwaukee favorites for the year!

 

Retired Submarine

MANITOWOC, NORTHEASTERN WISCONSIN

Wake up in a submariner’s bunk inside the USS Cobia, a vessel used during World War II. Guests to this “SubBnb” receive a fun perk: private after-hours access to the adjacent Wisconsin Maritime Museum, which manages the submarine. Bring friends or family –the Cobia can hold up to 65 people and features more than 50 different spots to sleep. Thankfully, you won’t be on watch as this submarine’s been docked here for decades.

Douglas DC-3 Plane

DEERBROOK, NORTHERN WISCONSIN

During World War II, this plane flew U.S. Marines between Guam, Midway Island and Pearl Harbor. Its second chapter is as a snug Airbnb just north of Antigo. It’s been retrofitted with four beds and a full bathroom, but the cockpit still lets you experience what it might have been like to fly the boys around the Pacific Theater. And it’s still Wisconsin; you can fish for bass on the private lake, or grill up some brats on the deck just behind the wings. 

Holiday Music Motel 

STURGEON BAY, DOOR COUNTY 

This 1950s motel – billed as the first built in Door County – was lovingly restored in 2009 and is likely the only motel in the world with its own radio station. Steel Bridge Radio plays 1,500 songs produced at the motel. Each of the 18 guest rooms, including the Elvis Room with its Formica pink countertops at the wet bar, is a delightful throwback to the middle of the last century, and one even houses a desk that’s been at the motel since 1952. 

Hobbit House

RIVER FALLS, WESTERN WISCONSIN

Literally built into a sloping hillside amid 3.6 forested acres, this 1972 earth-sheltered house may cause you to reimagine your life as a hobbit or fairy. The vibe inside this Airbnb is like a white-walled, arched-ceiling cave. It adds up to 2,300 square feet, but the listing suggests only bringing “those you have quite close relationships with” – as the unique architecture allows occupants of the two bedrooms to hear each other.  


This story is part of Milwaukee Magazine’s May 2026 issue.

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A seasoned writer, and a former editor at Milwaukee Home & Fine Living, Kristine Hansen launched her wine-writing career in 2003, covering wine tourism, wine and food pairings, wine trends and quirky winemakers. Her wine-related articles have published in Wine Enthusiast, Sommelier Journal, Uncorked (an iPad-only magazine), FoodRepublic.com, CNN.com and Whole Living (a Martha Stewart publication). She's trekked through vineyards and chatted up winemakers in many regions, including Chile, Portugal, California (Napa, Sonoma and Central Coast), Canada, Oregon and France (Bordeaux and Burgundy). While picking out her favorite wine is kind of like asking which child you like best, she will admit to being a fan of Oregon Pinot Noir and even on a sub-zero winter day won't turn down a glass of zippy Marlborough Sauvignon Blanc.