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.
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.
Lamppost 15 is everything you want in an Airbnb. It’s affordable, has enough room for a small crew, and is located near the commercial center of Bismarck. You can escape to attractions including Fort Abraham Lincoln State Park or a Lewis & Clark Riverboat Cruise. Or you could hit the Missouri River on your own tubes or kayaks. We wouldn’t blame you if you booked an extra night to try all them, leaving time, of course, to lounge around Lamppost 15 and challenge your travel partners to a round on the Ms. Pac Man machine.
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.
Of course, no Midwest road trip is complete without at least one night in a tent. The Lazy Oaks Glamping site is set up for success with a spacious tent on an elevated platform, complete with a queen-size bed and a patio for lounging. By night you’ll doze to the call of bullfrogs and the songs of owls. By day you’ll explore the 11 acres of private land and the surrounding countryside.
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.
Nobody ever said all yurts have to play by the same rules. The most wish-listed Airbnb in Missouri is a wood-framed yurt whose top more resembles the white-capped peaks of the Rockies than it does that of a Central Asian traditional dwelling. This is to your advantage, as the accommodation is both warm and cozy, without sacrificing its rustic charm. You’ll be surrounded by the Ozard forest and all the tranquility therewithin.
This cabin sums up everything that the most wish-listed Midwest retreat should be. It’s surrounded by a forest with plenty of deck space; wildlife sightings are common and diverse; and the home is a great place to prepare a home-cooked meal. The listing also touts the accessibility to hiking and golf. Though with the onsite library and fireside reading space, this spot is the perfect point in the trip to simply cozy up with a book and let the logs crackle.
Sixteen guests, six bedrooms Price: $941 per night
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.
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.
The coffee view from Ryan’s Place Cabin is the best in the Midwest — open the doors to gaze out and you’ll feel as though you’ve awoken to the Serengeti Plains right here in the middle of Illinois. The Rhymer Nature Preserve is nearby, as are more local fruit and cheese vendors than you could hope to visit in one trip here. The spot was built in 1865 and retains its historical charm, albeit with modern conveniences and a high level of comfort.
From the outside, Birdsong looks much like many other large barns converted into cozy retreats on Airbnb. It’s the inside that separates this incredible property from the rest. It’s perfectly furbished with a hot tub, modern kitchen, and spacious living area. There’s a pool table, reading room, and bedrooms that gaze upon open pastures. And while the hot tub takes all the glory, it’s actually the jacuzzi tub indoors that is the real hero of relaxation here.
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.
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.
