Wisconsin is a fascinating state to explore.
From its stunning natural beauty to its vibrant cities and quaint small towns, there’s something for everyone in America’s Dairyland.
In this blog post, I’ll introduce you to a range of one-of-a-kind accommodations, from treehouses and castles to lighthouses and converted train cars. There’s even a submarine on this list!
Whether you’re seeking adventure, romance, or simply a change of pace, these are some of the best places to make your Wisconsin getaway unforgettable.
So let’s dive in and explore the Badger State’s most unique places to stay!
If you’re planning to stay closer to the city, don’t miss our list of the 25 Coolest Places to Stay in Milwaukee for a unique urban experience.
1. Coulee Junction Caboose
Coulee Creek Rd, Ferryville, WI 54628
If you’re looking for a truly unique and secluded place to stay in Wisconsin, look no further than this charming 1954 Red Railroad Caboose.
The Coulee Junction Caboose is nestled on five wooded acres just four miles away from the Mississippi River, and it’s a one-of-a-kind vacation rental.
The caboose has been lovingly restored and updated to include all the modern amenities you need for a comfortable stay, including a conversation area, a fully equipped kitchen, a new bathroom, and a cozy gas fireplace.
Sleeping up to four guests, the caboose features a double size futon and a set of bunk beds.
But the real highlight of this property is the outside deck and hot tub, where you can soak and relax surrounded by nature at its best.
This is a great place for families, many of whom left reviews about how much their kids loved it.
Hiking and wineries are nearby, reviewers say the owner is very responsive.
Book your stay at the Coulee Junction Caboose >>
2. Lake Superior Barn
11251 Rudolphs Rd, Maple, WI 54854
Lake Superior Barn is the perfect retreat for those seeking a distinctive and rustic experience.
Situated on 320 acres of remote wilderness and a sandy beach on the south shore of Lake Superior, this 4,250 square foot home easily accommodates up to 20 guests in its 6 bedrooms and 4 bathrooms.
The open bathroom design and individual toilets and showers make it ideal for multiple families to stay together.
Take in the stunning 180-degree views of Lake Superior from the outside shower or 1600 sq. ft. reclaimed deck while enjoying the 60-70 degree temperature of the shallow and sandy bottom waters.
Lake Superior Barn features a fully equipped kitchen, pantry with extra ingredients, and a game room with radiant concrete heat for chilly days.
With no other homes on the Lake Superior shoreline for miles, this unique destination offers the perfect secluded retreat.
Explore the surrounding Brule River State Forest, pick raspberries and wild strawberries in the summer, or snowshoe the trails in the winter.
The property also boasts a private creek for swimming and wandering deer trails. And don’t forget to end your day with a fire on the bluff, watching the summer sun set over the hills of Duluth.
Located 30 minutes east of Duluth and close to popular attractions like the Apostle Islands and Bayfield, Lake Superior Barn is an ideal place for those seeking a peaceful getaway from a hectic life.
3. Boulder Ridge Treehouse
35400 Co Hwy J, Bayfield, WI 54814
Experience the ultimate northwoods retreat at Boulder Ridge Treehouse, the only treehouse in the stunning Bayfield area of Apostle Islands, Wisconsin.
Surrounded by pine trees and nestled in berry country, this handcrafted treehouse boasts a double loft with a catwalk and two sleeping areas, all enclosed by beautiful driftwood railings made from Lake Superior wood.
The property features walking trails, a pond, and is located just a few miles from the beach, orchards, berry fields, and wineries.
Don’t be surprised if the owner’s friendly border collie, Janie, pays you a visit and plays soccer with your kids.
4. Anaway Place
29493 State Rd 80, Richland Center, WI 53581
If you’re planning a stay at Anaway Place any time in the next two years, the time to book is now.
This stunning glamping destination in Southwest Wisconsin is a collection of distinct cabins surrounded by nature that will take your breath away.
The Glass House has walls that are completely, yes, made of glass. You’ll feel completely at one with the elements.
The Meadow House has 360 degree views of the wood and prairie with gorgeous reclaimed oak floors and natural light throughout.
The Woodland House boasts an iconic spiral stairway, and a Hase wood burning stove.
And the sizable barn is an ideal setting for large groups of families or friends to stay together, with a warm harvest table, wood-burning stove, and a loft.
The new Hillside Cabin is a curvy wonder with a rounded view of the valley woods.
And the log cabin has old timber walls, a loft tub, and beautiful back deck to settle in under the stars.
5. Pirate Ship Adventure Cabin
Juneau County, WI
Set sail on a pirate ship adventure like no other! The “Passing Wind” pirate ship is located just 15 minutes from the theme parks of the Wisconsin Dells and close to Mirror Lake, Devil’s Lake, and more.
This unique lodging option is perfect for those looking for an adventure and a break from traditional hotels. The ship is fully decorated in the theme of the Caribbean, providing an immersive experience for guests.
While most of the ship is outdoor space, the mid-ship deck is private and has seating and a table, while the two upper decks are perfect for sunning and relaxing. The ship sleeps six, making it great for families with children or couples.
It’s worth noting that the captain’s quarters and the crew bunk room are a short walk across the lower deck outside from each other, about 15 feet apart. They are not connected, which may be an issue for younger children who may not want to be too far from their parents.
6. St. Kate The Arts Hotel
139 E Kilbourn Ave, Milwaukee, WI 53202
St. Kate The Arts Hotel is a boutique hotel located in the heart of the downtown area in Milwaukee, and it’s dedicated to celebrating and promoting the arts. It’s one of the best hotels in Milwaukee, winning esteemed awards and rave reviews from the likes of Conde Nast.
The renovated hotel is housed in a historic building that was originally built in 1893 as the Button Block building.
One of the most unique features of St. Kate The Arts Hotel is the artwork that is on display throughout the property. The hotel’s collection includes pieces from local artists as well as nationally recognized artists, and the artwork is rotated regularly to provide guests with new experiences during each stay.
The rooms are also designed with art in mind. Each room is decorated with unique artwork, and the furnishings and decor are inspired by the hotel’s dedication to the arts. The rooms are comfortable and luxurious, with modern amenities like free Wi-Fi and flat screen TVs.
Saint Kate also hosts a variety of events and performances throughout the year, and has its own on-site restaurant black box theater, which is used for performances and rehearsals.
St. Kate The Arts Hotel is one of the most unique hotels in Wisconsin. Whether you are an art lover or just looking for a comfortable and luxurious stay in Milwaukee, this boutique hotel offers a one-of-a-kind experience that you won’t find anywhere else.
Plus, it’s just steps away from the Marcus Center for the Performing Arts, and a short distance from Lake Michigan, Milwaukee Art Museum, Bradley Symphony Center, and other downtown attractions.
Book your stay at St. Kate The Arts Hotel >>
Looking for other options in Milwaukee? Other unique hotels include the Iron Horse, Hotel Metro, the Kimpton Journeyman Hotel, and the Pfister, listed on the National Register of Historic Places.
7. The Bent Beam Barn
Briggsville, WI
Escape to the countryside of Briggsville, Wisconsin for a unique stay at the Bent Beam Barn.
This renovated dairy barn, just footsteps away from Mason Lake, has been beautifully restored with custom-made rustic furniture, farm decor, and antiques for a nostalgic look and a cozy feel.
The property boasts ample space for relaxing and all kinds of activities, including a large fire pit, spacious yard, and access to Mason Lake for boating, kayaking, or canoeing.
Enjoy breathtaking sunsets over the lake from the deck or gather with friends and family in the open kitchen and living room concept.
With three levels of living space, including a game room (Milking Parlor), the Bent Beam Barn offers something for everyone.
Most of the decor in the game room comes from local farms, adding a special twist to the space.
Local restaurants in Briggsville are only a few minutes away, and the property is just fifteen minutes from the famous Wisconsin Dells, known for its attractions and restaurants.
Book your stay at the Bent Beam Barn >>
8. The Croquet Cabin
This cozy cabin is located in a peaceful and secluded area in the Northwoods.
The tiny house has slate floors and wood walls and ceilings, providing a romantic and cozy ambiance for couples. The property is 2 acres and is located right on the shore of Lower Gresham Lake.
The little gingerbread house is well-lit at night with over 75 vintage Coleman lanterns.
Guests can enjoy the sunset at the lake front bonfire pit, have coffee or cocktails on the pier, play croquet on a professional court, or grill court side on a patio surrounded by flowers and forest.
9. The Lighthouse
Kewaukee County, WI
The Lighthouse is a unique, custom nautical-themed estate located on 2.5 acres of private, secluded land with 265 feet of water frontage.
With a commercial-grade kitchen, 6000 sq ft of living space, 5 decks, and waterfront views from every room, this property is designed for family fun.
The Lighthouse has 6 bedrooms (plus a loft) with 18 beds total, and can comfortably sleep 28. There is a private pebble beach, kayaks, fishing gear, and outdoor games available for guests to enjoy.
The Adventure Shed provides kayaks, bikes, and more.
The newly renovated game room has arcade games, a pool table, shuffleboard, electronic dartboard, and a bar.
The property also includes a private tennis/basketball court, mowed walking trails, and snow shoes and sleds in the winter.
All of these amenities make The Lighthouse perfect for a family getaway, friends retreat, or corporate gathering.
10. Nordley’s Metal Lark Tower
1120 Clam Falls Dr, Frederic, WI 54837
MetalLark Tower is an 800 sq.ft. cabin situated in the trees with stunning views of a hidden lake and wildflower meadows.
It has a king bed with organic mattress and linens, one hide-away bunk bed, and an ensuite bathroom with a jetted spa shower.
The living area is located on the second floor, and the cabin features floor-to-ceiling glass, two gas fireplaces, a full chef’s kitchen, a desk nook with a European pull-down bunk bed, and a “floating” balcony.
Other amenities include central heating and air conditioning, free WiFi, a projector monitor for streaming services, boosted cell phone signal, in-cabin laundry, outdoor fire pit and gas grill, and solar-powered energy.
Book your stay at Nordley’s Metal Lark Tower >>
11. Jungle House in New Berlin
1920 South Springdale Road, New Berlin, WI
Escape to paradise in southern Wisconsin at the Garden of Eden, a unique oasis on 17 acres of secluded forest and lake just a short drive from Chicago and Milwaukee.
This nature lover’s paradise features a 3.5-acre spring-fed lake stocked with fish, canoes, kayaks, stand-up paddleboards, and many more water toys.
The sandy beach is perfect for kids and adults, with fire pits and s’more kits included for a cozy evening under the Northern Sky.
Inside the 5,500 sq. ft., 6-bedroom, 7-bathroom home, the great room features 20-foot southern-facing windows and skylights to immerse you in nature.
The indoor pool is perfect for kids and adults, and the fully-stocked kitchen can accommodate gourmet meals or frozen pizzas.
With seating for 16 around the dining room and kitchen, the custom butterfly chairs, and the game and theater room with over 50 games, every inch of the Garden of Eden is designed to create fun and special memories with friends and family.
12. WWII Submarine
Manitowoc, WI
This may be the single most unique place to stay in the state of Wisconsin.
Make history when you stay aboard the fully restored USS Cobia, the best preserved World War II submarine in the country, now offered as a unique Airbnb experience by the Wisconsin Maritime Museum.
The Sub Bnb sleeps up to 50 people in sailors’ bunks throughout the boat, and the price includes admission for the first five guests.
The submarine has been meticulously restored with amenities added like heat and air conditioning, making it perfect for year-round overnight visits.
During your stay, you can explore the submarine and enjoy a personalized behind-the-scenes tour through the boat, and you’ll have access to the entire museum after hours.
Showers and restrooms are available in the museum, and a light breakfast and freshly brewed coffee will be served in the morning.
13. Camp Wandawega
W5453 Lake View Dr, Elkhorn, WI 53121
Camp Wandawega is a historic summer camp located in Elkhorn, Wisconsin that has been converted into a unique vacation destination.
The camp dates back to 1925 and has been beautifully preserved to retain its rustic charm. Guests can stay in a variety of vintage cabins, tents, and even a treehouse while enjoying activities such as canoeing, archery, and arts and crafts.
The camp also hosts special events and retreats, and has been featured in various media outlets for its unique style and character.
14. Pink Castle Bae-Cation
Hudson, WI
This rosey oasis screams “Girls Weekend”.
Pink Castle is a stunning Victorian mansion that will transport you to a world of over-the-top glamour and luxury.
Built in 1883, this 4,400 square foot home boasts unique and lavish decor in every room, including a mermaid-themed living room and a dining room with giant golden thrones.
You can even rent a pink escalade or a pink moped to complete the experience!
With a workout room, WiFi, and a full kitchen, you’ll have everything you need for a comfortable stay.
And don’t forget the outdoor amenities, including a huge outdoor pool that’s always heated to 90 degrees, a hot tub with a massage seat, and a pool house where you can set up your own bar.
Instagram-worthy and sure to be memorable, the Pink Castle is an excellent choice for a bachelorette celebration or a fun-filled family vacation.
15. Beechwood Cottage
Sister Bay, WI
Escape from the hustle and bustle of everyday life and immerse yourself in the serenity of the countryside at the picturesque Beechwood Cottage, just a short 5-minute drive from Sister Bay in Door County.
Tucked away on a private, wooded lot spanning 1.6 acres, surrounded by beechwood trees, this charming retreat offers the perfect combination of rustic charm and modern comfort.
Step inside and you’ll be greeted by a warm and inviting mid-century modern decor, thoughtfully curated to ensure that every detail is just right. The oversized windows let the natural light flood in, providing breathtaking views of the lush greenery outside.
The main floor boasts a fully-equipped kitchen, an open living room with high ceilings, and a remodeled bathroom with a walk-in glass shower. The bedroom on the main level is furnished with a plush memory foam queen bed that guarantees a good night’s sleep, while a washer and dryer are available for your convenience.
Upstairs, the spacious loft awaits, featuring another memory foam queen bed, a comfortable sitting area, and expansive windows that offer stunning panoramic views of the surrounding landscape.
16. Starlight Tower Manor Observatory
W5709 Fox Hill Rd, Fort Atkinson, WI 53538
The Starlight Tower Manor is an 8-9 bedroom, 3-4 bathroom, 11-12 bed luxury manor located in Fort Atkinson, Wisconsin.
With over 8100 – 8750 sq. ft. of space, it offers a unique experience with an observatory, telescopes, a vintage arcade gallery, a rock star room, and a 35-seat movie theater.
The star of the show at the Starlight Tower Manor is undoubtedly the Sky High Viewing Tower Lounge Observatory, which provides stunning views of the surrounding countryside both during the day and at night when guests can use the telescopes to gaze at the stars and planets.
Families will have a great time in the game room, complete with a pool table, ping pong, foosball, and video games. The kitchen is fully stocked with marble countertops, custom black maple cabinets, and a large dining area seating up to 20 people. There’s also a gym!
The first floor is handicap accessible, including a sit-down shower with grab bars and a bedroom with 2 double beds.
The Starlight Tower Manor can sleep up to 35 people with the use of couch beds and large tent setups. An add-on honeymoon hot tub love suite is available.
The destination is perfect for weddings, meetings, special events, and retreats with extra fees.
17. Barndominium With Goats
Winneconne, WI
The Cloverland Barndominium is a unique 100-year-old barn located on 5 acres of private forest, beside a river in Winneconne, Wisconsin.
Guests will have the opportunity to explore the private trails, enjoy canoeing on the river, make a fire in the fire pit, and feed the friendly goats and chickens from the comfort of their window.
The 2-bedroom home has been thoughtfully restored while retaining its old charm, and you’ll have access to all modern amenities such as fast wifi, smart TVs, and a fully equipped kitchen.
This “barndominium” is conveniently located a short drive away from popular destinations such as Oshkosh, Appleton, and Lambeau Field in Green Bay.
18. Seth Peterson Cottage
E9982 Fern Dell Rd, Reedsburg, WI 53959
The Seth Peterson Cottage is a stunning architectural gem located in Mirror Lake State Park, Wisconsin.
It was designed by Frank Lloyd Wright in 1958 for a young schoolteacher named Seth Peterson who wanted a beautiful and affordable retreat for himself.
What makes this cottage unique is its design – it is a beautiful example of Wright’s organic architecture.
The cottage is built into a steep hillside and appears to grow out of the surrounding landscape. Its interior features beautiful redwood walls and ceilings, large windows that offer beautiful views of the forest, and a beautiful stone fireplace.
The cottage is also unique because of its history. After Peterson’s death, the cottage fell into disrepair and was almost demolished. However, a group of concerned citizens banded together to save it, and it was eventually restored to its former glory.
Today, the cottage is owned by the Seth Peterson Cottage Conservancy and is available for vacation rentals. It offers a unique and unforgettable experience for anyone looking for a beautiful and historic getaway.
19. Castle La Crosse
1419 Cass St, La Crosse, WI 54601
Castle La Crosse is a unique bed and breakfast located in a historic Victorian mansion in La Crosse, Wisconsin. The mansion was built in 1892 and was restored to its original grandeur in 2000, including the addition of modern amenities.
The castle features six guest rooms, each with a private bath and decorated with antique furnishings. The rooms have different themes, such as the Royal Suite with a four-poster king bed and a private balcony overlooking the Mississippi River.
Guests can enjoy a gourmet breakfast each morning and relax in the common areas, such as the parlor, library, or dining room, which feature period furnishings and decorations.
It’s in a perfect location in a scenic area near the Mississippi River with easy access to downtown La Crosse, where guests can find shopping, dining, and entertainment options. It’s also near several outdoor recreation areas, including parks, trails, and waterways.
Castle La Crosse offers a unique and luxurious experience for guests looking for a historic and charming place to stay in Wisconsin.
Looking for other options? The Charmont Hotel is another unique place to stay in La Crosse.
20. Don Q. Inn
3658 WI-23, Dodgeville, WI 53533
The Don Q Inn in Dodgeville, Wisconsin is known for its quirky themed rooms, and there’s a real airplane parked outside!
The rooms range from space themed to jungle themed, and there are even suites with a boat-shaped bed, an igloo, and a tipi, a space capsule, and a hot air balloon.
There’s also an indoor and outdoor pool with a whirlpool for guest use.
Note: According to reviews, the hotel is quite dated. I recommend reading reviews carefully before you book a stay there.
21. Architect Gem
Ellison Bay, WI
This stunning property located near Ellison Bay in Door County is a unique architect’s gem that boasts breathtaking views of the surrounding landscape.
Secluded enough to provide privacy, yet close enough to town to offer convenience, this home is the perfect escape from the hustle and bustle of everyday life.
The main house features a spacious living area, a fully-equipped kitchen, a dining room, a shower bath, and a loft bedroom.
Additionally, there’s a newly-finished “Garage-Mahal” that comes with a full bathroom, two bedrooms, a kitchenette, and a small living room with a sleeper. This separate space is perfect for older children who want to have their own private area.
Built as an architect student’s “design build” project, this home has unique angles and details that you won’t find anywhere else in the world, making it a one-of-a-kind vacation spot.
Guests have access to the lake via a wood and steel staircase, which leads down to the water.
Activities like swimming, fishing, and other water sports can be enjoyed right from the shore.
Note: Due to the steep cliff, this property is not suitable for young children or pets.
22. Adeline’s House of Cool
Markesan, WI
Adeline’s House of Cool is a family-owned and managed Airbnb rental that promises to provide a memorable experience for everyone, whether for families, friends, or couples.
The property is located near Lake Puckaway, offering guests private pier and channel access for fishing, boating, kayaking, and other water activities, even in the winter.
The rental features 6 cozy bedrooms, each with individual access to a screened-in wrap-around deck with hanging benches, a great room with a wood-burning fireplace and an entertainment center, a game room with a wet bar, a 20-foot indoor hot tub, and various antique games and treasures to discover.
Outside, there’s a wrap-around deck, spacious grounds with a large fire pit, an antique telephone booth, and several unique features to explore.
Adeline’s House of Cool is available year-round, and pricing varies depending on the season and number of guests.
The rental also offers ample parking and the possibility to rent pontoon boats, which can be delivered to the cabin for guests to enjoy.
23. Wisconsin Treehouse Getaway
Racine, WI
This Treehouse Airbnb is a unique and secluded space that has been featured in Timeout Magazine as one of the Top 10 secluded Airbnbs in the Chicago area and one of Wisconsin’s Top 5 Airbnbs.
It is described as an immersive nature experience, overlooking a creek and woods, with all modern comforts. The space is a private apartment with a full kitchen, bathroom, bedroom, and living room, and it has a separate entry from the main house.
You’ll have access to a private patio and a screened-in gazebo that overlooks the creek, where you can enjoy a meal or relax with a fire pit.
The apartment is suitable for couples celebrating special occasions or families of up to five guests.
The property is located in Racine and is close to various attractions, including the Racine Art Museum, Racine North Beach, and the Racine Zoo.
24. Main Street Loft
Lake Geneva, WI
This listing offers a unique lodging option located in the heart of downtown near Geneva Lake, shopping, fun bars, and delicious restaurants.
The tents/suites have been designed with comfort, style and fun in mind, with a full kitchen and bar including swings for added fun.
Guests can choose to dine in using the oversized custom table inspired by Geneva Lake, or explore the town’s dining options.
It’s a great choice for a Girl’s Weekend, Bachelorette group, birthday getaway, or small celebration.
Note that there is a dance studio located above the unit that may cause moderate noise during classes on weekday evenings.
Book your stay at the Main Street Loft >>
25. Riverside Retreat Glamping
This unique glamping experience is located on a beautiful 3-acre property in northern Wisconsin, close to Duluth/Superior and lakes.
The canvas tent is set on a bend of a river with a pond nearby, allowing guests to enjoy the calming sounds of water flowing and birds singing. The tent includes a fireplace/wood stove, mini fridge, Keurig, microwave, and more.
Outside, you can take advantage of a firepit, picnic area, outhouse, hammock, and more. There is no plumbing, but firewood and a 5-gallon water jug are included in the stay.
Bedding is provided for one full-size bed, with sleeping bags available for the futon. However, there is no Wi-Fi, and cell coverage can be spotty.
Honorable Mentions:
Luxe Barn
Walworth, WI
This luxe barn vacation rental in Walworth, Wisconsin is a unique and spacious property that was custom-built using original barn wood.
Cranberry Castle:
Eagle River, WI
With 8,500 square feet under air, Cranberry Castle is a 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.
Lakefront House with Private Sauna
Madison, WI
This downtown lakefront home in Madison, WI is steps away from the action of Willy St. and State St., and there’s an electric barrel sauna overlooking the lake.
I hope these unique destinations help you plan a memorable getaway with your family!
Did we miss something? Email us at hello@mkewithkids.com.
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Calie Herbst, Editor-in-Chief of Milwaukee With Kids, has spent over a decade combining her experiences as a parent of three to create a hub for Milwaukee’s family adventures.
Her decade-long teaching career in Milwaukee Public Schools and academic background, including a Master’s in Teaching from Marquette University and dual B.A.s in Sociology and Spanish from the University of Wisconsin – Madison, fuel her passion for inclusive and engaging family content.
Calie is also a recognized voice in local media, contributing to WISN Channel 12 News, WTMJ Wisconsin Morning News, Fox 6’s Real Milwaukee, and B93.3.
Discover more about Calie’s journey and editorial approach on her About Page and Editorial Policy Page.
