The most unique vacation rentals in Wisconsin on Airbnb and VRBO
Wisconsin, affectionately called the Cheese State, has a lot to offer. There is something for everyone. From the bustling cities to the South, to the fantastical small towns and big houses along the shores of the Great Lakes, to the action packed Northwoods and Wisconsin Dells - there is fun for everyone. We love exploring all that Wisconsin has to offer and our favorite ways to stay are in our very own rental space. We have written before about luxury vacation rentals and some amazing cabin options in Wisconsin, but we have recently found the state is just packed full of unique vacation rentals that you just don’t see every day. Have you ever wanted to stay in a caboose from the last century? How about a house that has it’s very own private roller rink? Those options can all be yours for the perfect vacation!
Check out our list below. These houses are either featured on Airbnb or VRBO. Below each listing we will include helpful information like how many people can sleep at the house, where it is located, and highlight any special details. There are 20 in total, so if you are looking for a specific one, just keep scrolling. The orange text included with each rental will take you directly to where you can find more photos, availability, pricing and book your stay!
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1954 Railroad Caboose
Crawford County, Wisconsin. 1 Bedroom, 1 Bathroom, Sleeps 4.
How adorable is this amazing converted train car turned vacation rental? It is so creative - we love the train theming and all the details that still make it cozy. 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. Spend your days exploring the area and your nights relaxing b the fire pit. How cool is the hot tub deck?! Best part - it is pet friendly! Check out this link to find more photos and availability of this awesome train car renovation.
If you think this place looks epic, be sure to check out our entire article on converted train cars: amazing trains and caboose renovations on Airbnb or VRBO!
Dome Home on the Lake
Holcombe, Wisconsin. 3 Bedrooms, 1.5 Bathrooms, Sleeps 8.
Ok this dome home on the lake is so darn adorable. We absolutely love the hosts obvious flair for design and color choices throughout - form the cookware to the books on the shelves. This looks like such a quirky escape. You are right on the edge of Lake Holcombe so come ready to explore the water and all the lake front restaurants and bars you can reach by boat or car. Or just relax and take in those sunset views from the dock. The inside honestly looks so cozy but the outside is what drew our eye. We can just imagine hanging out with family in the gazebo or around the fire pit. The rental comes with 4 kayaks, a paddle board, a paddle boat and life jackets for guest to use. There is even an optional pontoon boat rental! Check out this link for more photos and availability of the Dome Home!
If a quirky dome home seems right up your alley - check out our list of epic dome homes you can rent on vacation!
The House of Hodags
Rhinelander, Wisconsin. 1 Bedroom, 1 Bathroom, Sleeps 4.
Welcome to the House of Hodags! This vacation rental themed after the mythical beast that is the mascot of the Rhinelander area. Create lasting memories at this unorthodox and family-oriented residence with a monster-themed twist in Rhinelander! Immerse yourself in the Hodag legend like never before If the Hodag is a new concept to you, take a moment to research and discover its intriguing story. Tailored for 1-2 adults and 1-3 children, this dwelling elevates your stay to extraordinary heights. This house is located right behind the Hodag store - in the center of town. This unique place is the perfect homebase for exploring the Hodag legend, and the Rhinelander area. Check out this link to find more photos and availability of the House of Hodags!
Family Time at the Barn
Maple, Wisconsin. 6 Bedrooms, 4 bathrooms, Sleeps 20.
This amazing rustic barn is the perfect escape for the family looking to reconnect. This barn is right on the shore of Lake Superior and is the only home on the shoreline for miles. You have miles of unspoiled beach and 320 acres of private forest surrounding you, creating the perfect space to connect with nature. You can only just make out the lights of the northern shore cities twinkling in the distance across the water. There is no WiFi or cable TV, but there are plenty of cards and boardgames, as well as a game room to keep the family entertained with one another. Don’t miss the chance to relax by the driftwood fire and roast s’mores! Check out this link to find more photos and availability of the Lake Superior Barn!
If staying in an awesome renovated barn trips your fancy - why not check out our list of stunning barns and barndominiums you can rent on Airbnb or VRBO!
Loon Lodge with Roller Rink
Hatfield, Wisconsin. 5 Bedrooms, 6 Bathrooms, Sleeps 15.
Can you say that you have stayed in place that had its very own roller rink?! Well now you can! Loon Lodge has just that - plus enough space for your entire family. How much fun would this be a family get together, birthday party, or relaxing weekend away! You won’t ever have to leave this place to have a rad vacation - there’s a restaurant style kitchen, a bar, a pool table, and even a fire pit to get some fresh air. You are also close to Lake Arbutus, where you can lauch a boat or explore that natural area. So put on some music and skate the night way! Check out this link for more photos and availability of Loon Lodge!
Off Grid Inn
Fall Creek, Wisconsin. 1 Bedroom, 1 Bathroom, Sleeps 4.
Ok this fun and quirky tiny house is just begging to be your next instagrammable adventure. This is an ideal retreat for an individual or couple looking to escape to the wilderness, but without having to worry about the hassle of camping. You will definitely still feel a connection to nature though as the huge glass windows let in the outdoor vibes. This place is definitely off the grid - so do expect things like well water and a composting toilet - but the hosts do have a Verizon WiFi hotspot so you aren’t totally without the comforts of home! Bring a good book - this is the perfect place to read. Check out this link to find more photos and availability of the Off Grid Inn!
The Pink Lady
Milwaukee, Wisconsin. 2 Bedrooms, 2 Bathrooms, Sleeps 8.
Wow, this place just screams girl’s weekend. Located in Milwaukee’s downtown, this amazing bachelorette rental is perfect for your next birthday, or small celebration. We love what they have done with color and space - you will be snapping pictures and having fun all weekend long. Walk to shopping, dining, and fun right from your front door - or just hang out and have a night in with your full kitchen, champagne bar, and board games. Gals will love the double vanity when its time to get ready for a night out on the town. Check out this link for more photos and availability of the Pink Lady!
Twisting Twigs Garden Glamping Dome
Bayfeild, Wisconsin. 1 Bedroom, 1 Bathroom, Sleeps 2.
You will have so much fun at this glamping dome located on a real working organic farm in the woods. This is a true glamping experience, the dome does not have luxuries like WiFi or even electricity. This is the perfect place to unplug and unwind. You are located on 40 acres of super remote land, right next to thousands of acres of county land. If you are looking to visit the National Seashore - you will be very close, only about 6 miles away from Meyers Beach. There is a wood burning stove for those cold winter nights. Check out this link to read more about the Twisting Twig, see more photos and availability, and book your stay!
Prospect Place
Durand, Wisconsin. 3 Bedrooms, 1.5 Bathrooms, Sleeps 10.
Experience a unique getaway at this delightful vacation rental in Durand, Wisconsin, housed in a lovingly restored historic church. With two bedrooms and a loft, this property provides a distinctive accommodation option. Situated just a few blocks from the picturesque Chippewa River, guests can indulge in outdoor pursuits like kayaking, biking, and hiking, or simply bask in the tranquil ambiance of Durand and its charming surroundings. Check out this link to see more photos and availability of the beautiful prospect Place!
If you think that staying the night in a restored church sounds like fun, be sure to check out our complete list of restored churches on airbnb!
Lakefront Dome with Sauna
Cable, Wisconsin. 3 Bedrooms, 2 Bathrooms, Sleeps 8.
This unique dome is the perfect place to explore the Cable area from. It is just 15 minutes from Downtown Cable and the North End of the Birkie Trail Head. You can start with day with some warm coffee on the deck as you watch the sunrise over the lake and spend your evenings relaxing in the sauna and talking about how much fun you had that day. Inside the cabin there is a full kitchen if you want to cook at home, a great loft perfect for movie night, and comfy beds waiting for you when are are ready to to wind down. Check out this link for more photos and availability of this fun Dome Home!
Glamping Tent at Historic Big Rock Creek
Saint Croix Falls, Wisconsin. 1 Bedroom, 1 Bathroom, Sleeps 4.
This place is just simply adorable. One of the coolest glamping places we have ever see, and this one is tucked on a private estate complete with a lake stocked with trout. You can also enjoy 26 miles of trails, paddle boards, a swim raft and even canoes. Inside the tent you will find all the amenities you need for a rad vacation including a comfy queen bed, cast iron pan and propane grill, phone charging station, and even a coffee pot. What you are you waiting for?! Check out this awesome glamping tent today! Click this link to find more photos and availability of the Glamping Tent at Big Rock Creek!
Wilson Schoolhouse
La Crosse, Wisconsin. 2 Bedrooms, 2 Bathrooms, Sleeps 8.
Nestled in a peaceful rural setting, the Wilson Schoolhouse is a unique rental situated a short 8-minute drive from La Crosse's historic downtown. The rental encompasses the entire schoolhouse, comfortably accommodating 2 to 8 adults. Modern, plush furnishings replace the old school desks, providing a cozy space to unwind amid Wisconsin's picturesque hills. Originally constructed in 1917, the Wilson school served as a one-room educational institution until 1965. Recently restored and turned into a cool vacation rental, it maintains the "open" feel of the original structure, preserving its authentic character with the original slate blackboard and school desks. This historic gem is proudly listed on the City of La Crosse, State of Wisconsin, and National Register of Historic Buildings. Check out this link to find more photos and availability of the Wilson Schoolhouse!
Mill House Retreat
Belleville, Wisconsin. 1 Bedroom, 1 Bathroom, Sleeps 4.
Nestled in a picturesque park-like environment alongside the Sugar River, The Mill House Retreat offers a loft experience like no other. Dating back to 1864, this stone grist mill boasts impressive 15ft ceilings, preserving its original fittings and has now enhanced with lavish finishes. The space welcomes you with plush chesterfield sofas, a spacious bar area, and inviting beds. Situated just minutes from bike trails, art galleries, live music, restaurants, and bars, it provides a vibrant backdrop for your stay. Feel free to invite local friends to share in the experience and create lasting memories. Check out this link to find more photos and availability of the Mill House!
Shipping Container with Nordic Sauna
South Range, Wisconsin. 1 Bedroom, 1 Bathroom, Sleeps 2.
This unique rental is tucked right into nature and brings elements from the Nordic countries right to Wisconsin! Transformed from storage containers, Sölveig Stay offers a unique Nordic sauna and living area nestled in the serene woods, just half a mile from Lake Superior's sandy south shore. With a deliberate focus on minimalistic design, this space is tailored for two occupants, providing an ideal environment for rejuvenation and refocusing. Whether you seek a romantic escape, a spa retreat, or a workspace for your digital nomad pursuits, Sölveig Stay is thoughtfully crafted to inspire both creativity and relaxation. Check out this link to find more photos and availability of Sölveig Stay!
Brenner Tower
Ellison Bay, Wisconsin. 1 Bedroom, 1.5 Bathrooms, Sleeps 4.
You will have so much fun at the Brenner Tower - fully remodeled 2012, this place is one of the most unique rentals we have ever seen. The first floor boasts a family room and a convenient half bath with three separate doors for easy outdoor access. The master bedroom is located on the middle floor, featuring a shower and additional half bath positioned behind the bed. This floor also includes an office nook and floor-to-ceiling windows, ensuring a bright and airy atmosphere. Ascend to the third story where you'll find 360-degree windows offering stunning views of rolling fields, the Bay of Green Bay, and Washington Island. The kitchen is equipped with stainless steel appliances, granite countertops, and has an open concept design for a contemporary and inviting feel. Check out this link for more photos and availability of Brenner Tower!
1941 WWII Douglas DC-3
Deerbrook, Wisconsin. 1 Bedroom, 1 Bathroom, Sleeps 4.
Step aboard the 1941 WWII Douglas DC-3 Airliner, once an essential part of the United States Marines' military transport services connecting Guam, Midway, and Pearl Harbor. Now meticulously retrofitted for overnight comfort, this historic aircraft boasts modern amenities including A/C, heat, a bathroom, shower, and a fully equipped kitchen. Outside, a deck with a grilling area and a campfire pit are nestled among the trees alongside a private lake with a dock. Accommodating four guests comfortably, this unique experience allows you to sit in the fully restored and illuminated cockpit, offering a glimpse into the remarkable era of one of the most iconic aircraft ever built! Check out this link to find more photos and availability of this awesome plane!
Converted Historic Schoolhouse
Stockholm, Wisconsin. 1 Bedroom, 1 Bathroom, Sleeps 4.
Step into the Pleasant Corner Schoolhouse Retreat, a charming and recently renovated 1867 schoolhouse that has so much rustic and historic charm! This idyllic setting is tailor-made for couples, friends, solo travelers, and artists in search of solitude and tranquility. Nestled among the rolling fields and bluff tops of western Wisconsin, it's just minutes away from the charming towns of Stockholm, Maiden Rock, and Pepin. Whether you're exploring local galleries, hiking the nearby trails, or simply yearning for a peaceful escape, the Schoolhouse stands as the perfect getaway to fulfill your desires. Check out this link to find more photos and availability of this converted Schoolhouse!
Big Sky Barnhouse
Arena, Wisconsin. 6 Bedrooms, 3.5 Bathrooms, Sleeps 20+
Welcome to the Big Sky Barnhouse, a fusion of history and extraordinary luxury. This expansive barn accommodates over 20 guests with its 6 bedrooms and 12 beds, and spans 4 floors and over 7000 square feet. Enjoy a tube slide and an array of amenities that redefine comfort and entertainment. Inside, discover a 9-hole indoor mini golf course, a theater, home gym, and a game room featuring pool table, ping pong, darts, skeeball, and arcade machines. Step outside to find an in-ground heated pool, a spacious hot tub, sauna, 3 office spaces, a bunk room with an indoor basketball hoop, a patio, pergola, 3 decks, and a bonfire pit. Immerse yourself in the ambiance of local Amish barnwood furniture, black walnut doors, custom stonework, and the comfort of heated floors throughout. The Big Sky Barnhouse promises an unforgettable retreat with unparalleled luxury and charm. Check out this link to find more photos and availability of the Big Sky Barnhouse!
Getaway Tiny House
Wild Rose, Wisconsin. 1 Bedroom, 1 Bathroom, Sleeps 2.
A short drive from the Milwaukee, Getaway is the intersection of leisure and the great outdoors. Tucked away amidst acres of private woodlands, these spacious and thoughtfully designed individual cabins offer an ideal setting for a rejuvenating and inspiring retreat. Escape the routine and rediscover the essentials in this tranquil haven. Additionally, as a part of your reservation, indulge in complimentary firewood and s'mores, bringing a nostalgic touch to your welcoming getaway. Check out this link to find more photos and availability of this Getaway Tiny House!
Guesthouse on the Jahn Estate
Mequon, Wisconsin. 1 Bedroom, 1 Bathroom, Sleeps 2.
This fun cottage, on the National Registry of Historic places, has been converted into a romantic historic vacation rental. Originally built in 1844 as the Jahn Estate kitchen and smokehouse, it has been reimagined into your perfect homebase for exploring the area. There are modern conveniences like a kitchen and full bathroom to make you feel at home. The guesthouse is part of a larger estate that includes multiple properties and even a barn. The owners describe the property as our own idyllic hamlet and they cannot wait to share it with you. Check out this link to find more photos and availability of this fun little guesthouse.
Thanks so much for reading our list of super unique vacation rental options in Wisconsin. Did you have a favorite? Is there one we missed? We would love to hear from you! You can email us at seeseeksleep@gmail.com. Don’t forget to check out some of our other Wisconsin content:
Beautiful Cabins, Cottages, and Chalets for rent in Wisconsin
8 Spectacular Lodges on VRBO in Wisconsin (Link coming soon!)
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