Airbnb compiled its report of the most wish-listed stays in every US state so it’s time for a road trip with some epic accommodations. This road trip that connects the most wish-listed Midwest Airbnbs starts in North Dakota and heads south before turning north again and then back south, a rollercoaster of a road trip that’s even better than the crazy rides at Cedar Point.
Photo: Airbnb
This Road Trip Will Take You to the Most Wish-Listed Airbnbs in the Midwest
Here is a map covering the route of this itinerary:
We hope you love the coolest Airbnbs in the Midwest we recommend! Just so you know, Matador may collect a small commission from the links on this page if you decide to book a stay. Listed prices are accurate as of the time of publication.
Stylish 2-bedroom home — Bismarck, North Dakota
Named one of the coolest Airbnbs in North Dakota, this two-bedroom in downtown Bismarck is a great first stop. Its plentiful natural light floods into the four-season sunroom and the home has a modern, stylish decor throughout. All Bismarck downtown establishments, from restaurants to a swimming pool, a park, to shopping, are within walking distance, and the kitchen has everything you need to whip up a meal or make a picnic for the on-ward road trip. There’s off-street parking for two vehicles, too.
Eight guests, two bedrooms
$175 per night
Cabin at Green Mountain — Deadwood, South Dakota
Photo: Airbnb
South Dakota is the most underrated US state for its ease of access to incredible hiking and outdoor recreation. To spend as much time as possible outside during your time in South Dakota, book a night at the Cabin at Green Mountain. Here, just outside the mountain town of Nemo, you can hike and stargaze and porch hang to your heart’s content. You’ll also be close to Rapid City, Sturgis, and the Black Hills, including their famed monuments.
Six guests, two bedrooms
Price: $252 per night
Lakeside home with paddleboards and kayaks — Bellevue, Nebraska
You should take one or two days at this stop, as this lakeside location is the perfect place to relax and take some time away from behind the wheel. The six-bedroom home is within the top five percent of Airbnb listings, meaning it’s been awarded for exceptional guest reviews and host service. Each bedroom has smart TVs and blackout shades (so long lie-ins are almost guaranteed), and there are four bathrooms. Guests can use kayaks, paddleboards, other water toys, and beach gear provided by the rental and there’s a large deck area with a gas grill.
16+ guests, six bedroom
Price: $446 per night
Cozy cabin retreat — Tonganoxie, Kansas
This cabin retreat outside Tonganoxie, Kansas, includes a tree-hung hammock and an outdoor campfire area, and all the fixins’ of a good ole’ fishing cabin that got a luxurious makeover on the inside. It’s rustic yet comfortable, simple yet complete. The property has hiking trails, axe throwing, and even a labyrinth to keep you occupied. You’ll also have the option to participate in any activities happening at the adjacent retreat space, which could include anything from yoga to a heated chess tournament, depending on the group in residence.
Four guests, one bedroom
Price: $96 per night
Private luxury treehouse near Branson — Cape Fair, Missouri
Cape Fair, a quaint, unincorporated community in Missouri’s Ozarks, offers a serene stop on this Midwest tour. Situated on the shores of Table Rock Lake, a vast reservoir renowned for its clear waters and excellent wildlife spotting, Cape Fair is a playground for water sports, with boating, fishing, swimming, and kayaking opportunities. A stay here should be matched with an equally special rental, so we’ve gone for this top five percent Airbnb treehouse called Firefly. The custom-built luxury home is on a quiet hillside overlooking the Ozark hills. It’s under a mile from the lake and 25 minutes from Branson, where you can get groceries or have a meal out.
Six guests, one bedroom
Price: $150 per night
Remote 2-bedroom cabin — Guthrie Center, Iowa
Photo: Airbnb
The next stop on the route are the rolling hills of Iowa. Many small towns in the region have charming Airbnbs, one of which is Guthrie Center. This small town, founded in 1856, is ideal for those wanting a slower pace and a taste of authentic Midwestern hospitality. You can stroll through the historic downtown to admire the well-preserved Victorian-era buildings and hit up the weekly farmers’ market before retreating to this romantic and somewhat remote cabin. It’s on 40 acres with a fully stocked pond for fishing and various walking trails.
Six guests, two bedrooms
Price: $169 per night
Wolf House studio in northeast Minneapolis — Minneapolis, Minnesota
For being inside a major metropolitan area, the Wolf House studio sure feels remote. Walking into the living space is like entering a new world. You’ll feel like a hobbit among the rocked walls and ceilings and murals reminiscent of Middle Earth. Should you decide to venture out, the Minneapolis Arts District is just outside the door — perhaps justifying the unique artisanal approach that makes this property among the most wish-listed Midwest Airbnbs.
Four guests, one bedroom
Price: $214 per night
Tiny house off the grid — Fall Creek, Wisconsin
This property perfectly encapsulates the modern take on off-grid living. Remote and self-reliant, yes, but also comfortable, inspiring, and architecturally beautiful. You’ll really feel a part of nature here. A standalone sanctuary of wild awesomeness, this property in the Off Grid Inn complex is an ideal escape from the hustle and bustle of even the smallest of towns. You can hike or snowshoe, depending on the season. No matter when you come, brewing up a pot of coffee and gazing through the bay window into the forest beyond is always in order.
Three guests, one bedroom
Price: $271 per night
Posh mid-century A-Frame — Bloomington, Normal, Illinois
Another Airbnb within the top five percent, this stylish mid-century A-Frame is located in Bloomington. The home has all the mod-cons you need for a comfortable stay, such as smart TVs, so you can log into your streaming services and take a load off for a couple of days while lounging around. Outside, there’s a gorgeous private backyard with a patio with seating and fairy lights. Its location means you can park the car and walk to nearby grocery stores, dining, and local events like live music and the Saturday farmers’ market.
Six guests, three bedroom
Price: $225 per night
Modern Nashville Home in the Woods — Nashville, Indiana
In the hills of Brown County is the small town of Nashville, Indiana. It’s often called the “Art Colony of the Midwest” for its thriving (and very welcoming) community of artists, musicians, and craftsmen. Galleries showcasing a variety of mediums, from paintings and sculptures to ceramics and jewelery, line the streets, and music venues, including the Brown County Playhouse and the Nashville Opera House, host a diverse range of performances, from classical concerts to bluegrass shows. When visiting, opt for a stay at this new-build cabin. It has stunning views from its elevated balcony, a firepit for evenings under the stars, or you can cozy down inside for a board game by the fireplace.
Four guests, two bedrooms
Price: $225 per night
Fernside A-frame on the riverfront — Indian River, Michigan
There are two types of people in this world. Those who wish they lived in A-frame, and those who are lying (ok, technically there’s a third type, those who actually live in one — but these are less actual people than they are gods amongst mere mortals). This picturesque A-frame is in northern Michigan’s hill country, with lake activities at Mullet, Black, and Burt Lakes nearby as well as the state’s too-often-overlooked ski country.
Four guests, two bedrooms
Price: $585 per night
The Box at Treehouse Village — Dundee, Ohio
This modern take on a treehouse is a far cry from those of our childhood dreams. The Box at Treehouse Village is elevated with the surrounding Aspens and outfitted with the niceties of a luxury retreat. This spot is the perfect end to a road trip across the most wish-listed Midwest Airbnbs. Gaze out from the treetops at the surrounding hillside, raising a drink to the epic journey now behind you. 
Four guests, one bedroom
Price: $182 per night