Last Updated on May 25, 2021 by haveclotheswilltravel
One of my favorite things to do when we travel is to find unique and crazy places to stay. From a treehouse in the Amazon Rainforest to a Martian Tent in Wadi Rum and a hut on top of Mount Fuji – we’ve had some great experiences!
However, with being home in Wisconsin this summer, I didn’t want this crazy accommodation streak to end! And you know what – Wisconsin has some incredibly cool Airbnbs and vacation rentals to stay in. There are treehouses, yurts, tons of tiny homes, barns, silos and even a converted train caboose!
I’d love to hear which is your favorite Airbnb in the comments at the end of the post. Enjoy!
- Read next: 25+ Cool Things to Do in Wisconsin
- Read next: Awesome Cabins to Rent in Wisconsin
- Read next: The BEST Cabins in Door County
- Read next: The Coolest Airbnbs in Minnesota
The Coolest Airbnbs & Vacation Rentals in Wisconsin
*Disclosure: some of these links are affiliate links. Meaning, if you click a link and make a purchase, Have Clothes, Will Travel gets a very small commission at no extra cost to you. Thank you for supporting the brands that make this blog possible!
Tiny Houses
The Monarch’s Paradise – Green Lake, Wisconsin
This tiny house is so cool that it’s been featured on Tiny House Hunters! It’s also great for anyone looking for a place to stay during EAA, as it’s only a half-hour away.
- Click here to book this tiny house.
- Click here for more rentals in Green Lake.
Tiny House by Off Grid Inn – Fall Creek, Wisconsin
Immerse yourself in the forest of Wisconsin without sacrificing the comforts of home. This tiny home has everything you need with a fantastic view, no matter what time of year you stay here!
- Click here to book this tiny home.
- Click here for more properties in Fall Creek.
The Croquet Cabin Tiny House – Arbor Vitae, Wisconsin
A cozy little cabin located in the heart of the North Woods and on a lake. Perfect for a couple’s getaway!
- Click here to book this tiny house.
- Click here for more Arbor Vitae rentals.
Treehouses
Boulder Ridge Treehouse – Bayfield, Wisconsin
A handcrafted retreat near the Apostle Islands area – most of the wood used in the treehouse was harvested from the property!
- Click here to book this treehouse via Airbnb.
- Click here for Tripadvisor reviews.
Treehouse Queen and Bunk on Lagoon – Wisconsin Dells, Wisconsin
These treehouse units are perfect for families visiting Wisconsin Dells – as tickets to Noah’s Ark Waterpark & Timbavati Wildlife Park are included in their summer 2020 special. These also have 3 Indoor Pools, 1 Outdoor Pool, 3 Indoor Hot Tubs, 1 Outdoor Hot Tub, 3 Saunas, a Basketball Court, and Natural Lagoon on this property.
- Click here for more info on these treehouses. (NOT available in winter. Please check back in spring!)
Read next: The Coolest VRBO Rentals in Wisconsin Dells Featuring Waterparks, Cabins, Lake Delton & More!
Caboose!
1954 Rail Road Caboose – Ferryville, Wisconsin
Voted the BEST Romantic Get-Away in Wisconsin! This 1954 Red Railroad Caboose provides seclusion on five wooded acres located four miles from the Mississippi River. The Caboose features a conversation area, an updated kitchen, new bath and gas fireplace. A double-size futon and set of bunk beds provide sleeping for up to four people. Relax on the outside deck or in the hot tub while surrounded by nature at its best.
- Click here for more information on this rail road caboose.
Yurts
Yurtcation in Cambridge, Wisconsin
Enjoy the great outdoors in this yurt on a 17-acre semi-private lake. This yurt is also only 2 miles from downtown Cambridge and 20 miles from Madison.
- Click here to book this yurt.
- Click here for more rentals in Cambridge.
True nomad dwelling – Middleton, Wisconsin
Stay in an authentic Mongolia yurt in Middleton. This yurt is perfect for someone who wants to enjoy staying in a yurt – but only has to take a 100-foot stroll to the main house to use the shower, restroom and kitchen!
- Click here to book this yurt.
- Click here for more rentals in Middleton.
Frank Lloyd Wright House
Still Bend/Frank Lloyd Wright’s Schwartz House – Two Rivers, Wisconsin
The famous American architect Frank Lloyd Wright is from Wisconsin and has many of his incredible creations in our lovely state. This Airbnb allows you the chance to stay in one of his homes! This house has even been featured on the Travel channel’s Amazing Vacation Homes, The Wall Street Journal, The New York Times, Town and Country and more.
- Click here for more information on staying at this Frank Lloyd Wright home via Airbnb.
- Click here for info via Tripadvisor.
Hobbit House
G-ma and Pa’s Hobbit Home – Elk Mound, Wisconsin
Want to spend a night underground? Then this is the Airbnb for you. Plus, this home has a beautiful outdoor area to enjoy too.
- Click here for more info on this Hobbit home.
- Click here for more rentals in Elk Mound.
Glamping
Heated GLAMPING Yurt – Oshkosh, Wisconsin
Glamping = camping but far more luxurious. The host, Jessie, has several super cool Airbnbs to choose from as well. She not only has the gorgeous glamping accommodations pictured above, but also a vintage camper and a cute studio apartment.
- Click here for more info on this glamping experience with Jessie.
- Click here for more info via Airbnb.
Twisting Twig Gardens and Orchard Wall Tent – Bayfield, Wisconsin
This comfortable tent is located on a small organic farm and is about 6 miles from Meyers Beach in the Apostle Islands National Lakeshore.
- Click here to book this glamping experience in Bayfield.
- Click here for more rentals in Bayfield.
Barns
Luxe Custom Barn with Theater – Walworth, Wisconsin
Experience a stay like no other at this spectacular Walworth vacation rental! It was custom-built using the original barn wood, this well-appointed home boasts 6 bedrooms, 6.5 baths, and grand style! In warm weather, rent a boat, hit the beach in Fontana, golf, or hike in Kishwauketoe Nature Conservancy on the 26-mile lake path. In winter, come enjoy Wilmot Mountain Ski Resort or Alpine Valley, and after action-packed days, relax with a barbecue on the deck and a movie night in the theater room.
- Click here for more info on this luxe barn stay.
Maiden Rock Barn (Pine Creek Rustic Road) – Stockholm, Wisconsin
This is Wisconsin, after all, and I can’t make a list of cool Airbnbs without including a couple of barns! Although, most of these “barns” are nicer than my actual house, haha. The Maiden Rock Barn is just a few miles from the Mississippi River/Lake Pepin.
- Click here for more info on Maiden Rock Barn.
- Click here to book the Maiden Rock Barn via Airbnb.
Barn Stay – Oshkosh, Wisconsin
This barn hosts up to 16 people and has a large pond with Koi in the backyard as well as free-range chickens. There are also 2 silos that have been remodeled and one contains a unique spiral staircase!
- Click here for more info on this barn stay via VRBO.
- Click here for more info on this barn stay via Airbnb.
Silo
Silo Suite at Inn Greener Pastures – Chetek, Wisconsin
Or if you’d rather just stay in a silo – then this incredible Airbnb has you covered. This converted silo includes a private bathroom, bedroom and a top floor that overlooks a rock garden sculpture park.
- Click here to book this Silo suite.
- Click here for more stays in Chetek.
Shipping Containers
Life Uncontained – Viroqua, Wisconsin
If you’ve ever been curious about what it’s like to stay in a shipping container – now is your chance to find out! These are two shipping containers that have been converted into a 640 square ft. living space that features a private bathroom, full kitchen, 1 Queen size bed and sofa pulls out into twin bed, and a chair that unfolds into a single bed.
- Click here to book this shipping container.
- Click here for more cool stays in Viroqua.
Winery
Campo di Bella Winery & Family Farm LLC – Mount Horeb, Wisconsin
I don’t know about anyone else, but waking up on top of a winery is pretty much my idea of paradise! Campo di Bella has created a private retreat above their winery for guests to stay in.
- Click here to book a stay at this winery.
- Click here for Tripadvisor reviews.
Boats
Charming Sailboat Stay – Racine, Wisconsin
Stay aboard the 29′ sailboat “Clementine.” She is set up as a full-time Airbnb at Reefpoint Marina, which has amenities like a heated pool with two hot tubs, laundry facilities, Reefpoint Brewhouse restaurant, and top-notch shower facilities.
- Click here to book a stay on Clementine.
- Click here for more cool stays in Racine.
Pirate Ship Adventure cabin – Lyndon Station, Wisconsin
This pirate ship sleeps up to 6 people and is decked out in the coolest pirate-themed decor! (Your kids will love it.) Plus, it not far from Wisconsin Dells.
- Click here for more info on this pirate ship.
Luxury VRBO cabin stays
Indian Point Manor – Eagle River, Wisconsin
Indian Point Manor is a massive 9 bedroom house with modern updates and a rich history. Two additional carriage houses are available on the property’s vast 6-acre estate. The grounds include a boathouse with an upper-level game room, a private lookout over the lake and a full sized tennis court. An outdoor fire pit and grilling area are also located next to the main house among the meticulously groomed yard. There is also a hot tub.
- Click here for more info on Indian Point Manor.
Cranberry Castle – Eagle River, Wisconsin
With 8,500 square feet, this massive luxurious log and stone cabin is ready to make memories and has been featured on Travel Wisconsin, Discover Wisconsin and in the USA Today! The “Castle” is truly high end with no expense spared. This home also has a state-of-the-art home theater with comfortable seating for ten, an Infinity surround sound system with a 300-watt subwoofer and a popcorn machine (pre-measured packets provided).
- Click here for more info on this cabin.
Timber Shores – St. Germain, Wisconsin
Timber Shores immediately impresses guests with high, cathedral ceilings and an open concept floor plan. Giant wood beams sweep across the high ceilings adding a sophisticated alure to the bright, natural warmth of the home. The kitchen is state of the art with new appliances, granite countertops and everything you could need to entertain your guests while vacationing. The property has a private pier on Big Saint Germain Lake with plenty of space for watercraft of all kinds.
- Click here for more information on this luxury cabin.
Now, I’m curious, which of these Airbnbs is your favorite? Let me know in the comments!
Using a VPN When Traveling
VPN is short for “virtual private network.” A VPN (like IPVanish) sets up a private connection between your device and whatever network you are connected to – so, no one can see your browsing data. It is important to use a VPN anytime you are connected to public Wifi (such as at a restaurant, resort, hotel, cafe, airport, etc.). This is because when you connect to a public network no matter where you are, you run the risk of a hacker grabbing your unencrypted data. Trust me, speaking from experience here…this can put a real damper on your trip if your banking, phone or email get hacked while you’re traveling!
VPNs can also help you save on domestic flights, help you watch Netflix shows not available in the US and more! You can read more about using a VPN in my post “Why I Use a VPN When Traveling and at Home (And You Should Too).”
- Click here to download IPVanish VPN.
- Read next: Awesome Cabins to Rent in Wisconsin
- Read next: 25+ Cool Things to Do in Wisconsin
- Read next: The BEST Cabins in Door County
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- Read next: 7 Things to Know Before Visiting Door County, WI During COVID-19
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We love Twisting Twig Gardens Rustic Yurt in Bayfield, WI.
That is awesome! I am so happy to hear it!
Thanks for including our Pirate Ship!
It is such a unique place! Thank YOU for having such a cool accommodation option in Wisconsin!
I love this! Michael and I were talking about having a friends weekend at the Frank Lloyd Wright house last year!
Oooh! Let’s keep this in mind for next summer!