23 of the Coolest Airbnbs in Wisconsin – Featuring Treehouses, Tiny Homes, Yurts, Barns & More!

Last Updated on November 15, 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!

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


Tiny house hosted by Jessica

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.

Tiny House by Off Grid Inn - Fall Creek WisconsinTiny House by Off Grid Inn - Fall Creek Wisconsin

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!

The Croquet Cabin Cozy couple retreat in the woods

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!

Treehouses


Boulderridge Treehouse in Bayfield Wisconsin Boulderridge Treehouse in Bayfield Wisconsin

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!

Treehouse Queen and Bunk on Lagoon in Wisconsin Dells

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!


Newly Remodeled Romantic Get-a-Way!! 1954 Rail Road Caboose!! Relaxing Hot Tub!

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 YurtCation in cambridge wisconsin

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.

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!

Frank Lloyd Wright House


Still Bend/Frank Lloyd Wright's Schwartz House Still Bend/Frank Lloyd Wright's Schwartz 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 in Elk Mound Wisconsin

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.

Glamping


Heated GLAMPING Yurt | Oshkosh Outskirts
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.

Barns


NEW! Luxe Custom Barn w/ Theater & Fitness Room!

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)

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.

Barn stay Oshkosh Wisconsin

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

Silo Suite at Inn Greener Pastures

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.

Shipping Containers


Shipping container tiny house in Wisconsin

Shipping container tiny house in Wisconsin

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.

Winery


Campo di Bella Winery & Family Farm LLC

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.

Boats


Charming Sailboat Stay

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.

Pirate Ship Adventure cabin! Near Dells! Sleeps 6!

Pirate Ship Adventure cabin! Near Dells! Sleeps 6!

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.

Luxury VRBO cabin stays


NEW! Historic 9 bedroom estate on world's largest chain of lakes

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.

Top 10 Home On World's Largest Chain of Lakes! Featured on Travel Wisconsin!

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).

New! Gorgeous 5 bedroom vacation home on Big Saint Germain Lake!

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!

Need a housesitter while you are gone?


I, personally, recommend TrustedHouseSitters if you need to find a housesitter/someone to watch your pets while you are away.

How TrustedHousesitters works is they connect home and pet owners with trustworthy, verified sitters who won’t charge to look after your pets, in exchange for a unique place to stay. They have sitters and homes all over the world!

It’s a fantastic way to find trustworthy people to watch your home and pets while you are away. (And on the flipside, it’s a cool way to stay in different areas of the country and world without having to pay for accommodation! I have a friend who literally didn’t own or rent a home for years, and only used TrustedHouseSitters to find the next spot she was going to stay.) 

  • Click here for more information on TrustedHouseSitters.

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THE COOLEST AIRBNBS IN WISCONSIN – FEATURING TREEHOUSES, TINY HOMES, YURTS, BARNS & MORE!

THE COOLEST AIRBNBS IN WISCONSIN – FEATURING TREEHOUSES, TINY HOMES, YURTS, BARNS & MORE!

Coolest Airbnbs in Wisconsin

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