Whether you’re gearing up for a ski weekend, a biking adventure, or a stay in one of the most unique accommodations in the state, Wisconsin vacation rentals offer incredible places to turn a simple getaway into an unforgettable experience. We love finding stays that add to the adventure—whether it’s a cozy tiny home near a scenic bike trail or a fully decked-out retreat for a group getaway. Here are three of our favorite Wisconsin stays!
Big Sky Barnhouse – Merrimac, WI
If you’re looking for the ultimate home base for a ski weekend, Big Sky Barnhouse in Merrimac is hard to beat. Sitting less than a mile from Devil’s Head Resort, this vacation rental is packed with amenities designed for both relaxation and fun. After a full day on the slopes, soak in the hot tub, challenge your friends to a game of pool, or gather around the fire pit with a warm drink in hand.
But the fun doesn’t stop there. The house features a golf simulator, basement beach, sauna, and even an indoor slide, making it an incredible retreat for families or groups of friends.
Big Sky Barnhouse is just minutes from Parfrey’s Glen and Devil’s Lake, two of the best hiking destinations in Wisconsin. If you’re up for even more adventure, Wisconsin Dells is only a short drive away. While we love this rental in the winter, we can only imagine how fantastic it would be for a summer getaway!
📍 Book your stay: Big Sky Barnhouse on Airbnb
Tiny Home Near the Elroy-Sparta Trail – Norwalk, WI
If you love biking, this tiny home in Norwalk is the perfect spot to stay before tackling the Elroy-Sparta Trail—one of Wisconsin’s most scenic and historic rail trails. We spent a peaceful night here, enjoying the fire pit under the stars, before heading out for a full day of biking.
The home itself is small but well-designed, offering a quiet, cozy retreat after a long ride. It’s the perfect off-the-beaten-path stay for those exploring western Wisconsin’s trails, and it’s ideal for couples or solo adventurers looking for a unique experience.
📍 Book your stay: Tiny Home Near Elroy-Sparta Trail on Airbnb
Wisconsin’s Most Unique Airbnb – Stay aboard the USS Cobia
For a truly one-of-a-kind overnight stay, you can spend the night inside a WWII submarine! Docked in Manitowoc, the USS Cobia is an original World War II vessel that has been transformed into a floating Airbnb experience. This is hands-down one of Wisconsin’s most unique places to stay, offering guests the chance to sleep in actual crew bunks and explore the history of this legendary submarine.
The experience is immersive—stepping aboard feels like traveling back in time. You’ll hear the hum of the ship, see the original controls and periscopes, and get a real sense of what life was like for the sailors who served aboard. If you love history, adventure, or just a truly unusual stay, this is one experience you won’t forget.
📍 Book your stay: USS Cobia on Airbnb
WeWisconsin Tip:
If you’re booking a popular Wisconsin Airbnb (especially ski rentals or unique stays like the USS Cobia), plan ahead! These spots fill up fast—sometimes months in advance—so book early to lock in your dates.