Unique Places to Stay in Wisconsin: 17 Cool & Quirky Rentals
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Natasha Kayes
Author
As local travel experts, we know what travelers are looking for when it comes to finding the perfect accommodations for their next trip. To compile our lists, we scour the internet to find properties with excellent ratings and reviews, desirable amenities, nearby attractions, and that something special that makes a destination worthy of traveling for.
As with anywhere you travel, if you are planning a trip in Wisconsin, you have tons of options when it comes to where to spend the night. Where you stay can make or break your vacation, so we are determined to make sure you have some great choices. Whether you are putting together a nature-filled adventure exploring forests and waterfalls, a romantic getaway for two, a reunion with family or friends, or anything else, there are some really fun vacation rentals that will not only serve as the perfect home base for your activities but offer privacy, seclusion, and character that even the most unique hotels can’t provide. So, without further ado, let’s check out some of the most cool and unique places to stay in Wisconsin.
Tiny Home Rentals in Wisconsin
There is no denying the uniqueness of tiny homes, with all the comforts of a house tucked perfectly into a compact space. These particular little vacation rentals have far more to offer than meets the eye and are really cool places to stay in Wisconsin.
1. Tiny House on the River
- Address: Black River Falls, WI
- Size: 1 bedroom, 1 bath
- Price: $135/night
- Amenities: Heating/AC, fireplace, BBQ, Wifi, outdoor fire pit, EV charger
- Ratings: 4.9 Exceptional
Sitting right over the Black River in a quiet neighborhood, this tiny home offers a fully-stocked kitchen, plush furnishings (including a comfy day bed on the screen porch), a wall of windows to soak up river views in any season, and everything you need for the perfect getaway. The adorable Tiny House on the River is close to downtown shops and restaurants, trails, parks, and more.
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2. Bluebelle Tiny House in the ‘Hundred Acre Woods’
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- Address: Grand Marsh, WI
- Size: 2 bedroom (plus living room futon), 1 bath
- Price: $125/night
- Amenities: Wifi, pet friendly, AC, BBQ, fire pit
- Ratings: 4.6 Wonderful
Enjoy tiny living surrounded by natural beauty in this cute little rental situated on a nearly 100-acre property with a beautiful lake and lots of trails to explore - all less than 20 minutes from downtown Wisconsin Dells. Despite its size, the house sleeps six, with a queen bed in the bedroom, a loft with two twin beds, and a pull-out futon sofa in the living room. Great for families, the house is close to local attractions like Chula Vista Waterpark, Pirate’s Cove Adventure Golf, and Timber Falls Adventure Park. Check out the fantastic little Bluebelle Tiny House on Vrbo for more photos and availability.
3. Lupine Landing
- Address: Cornucopia, WI
- Size: 2 bedroom, 1 bath
- Price: $158/night
- Amenities: Lake view, Wifi, BBQ, fireplace, games
- Ratings: 4.9 Exceptional
Lupine Landing, the “tiny home on the big lake,” is small in size but huge on charm and comfort. Perfect for a weekend getaway, this lakefront cutie lets you enjoy spectacular views on the shore of Lake Superior, an all-season porch, vaulted ceilings, a fully-stocked kitchen (it even has a popcorn maker!), and the perfect location for exploring Cornucopia Beach, Meyers Beach, Port Wing, the Apostle Islands, and more.
A-Frame Rentals in Wisconsin
There is something about the shape of an A-Frame house that takes the appeal of a typical cozy cabin up to a whole new level. These sweet vacation rentals have loads of character and comfort for anyone wanting to get away.
4. A-Frame Cabin with Private Boat Dock
- Address: Butternut, WI
- Size: 3 bedroom (plus sofa bed), 1 bath
- Price: $207/night
- Amenities: Keyless entry, washer/dryer, AC/heater, Wifi, fireplace, washer/dryer, 2 fire pits, private boat dock
- Ratings: 4.8 Exceptional
This cozy, and not to mention pretty, A-frame cabin in Butternut is great for family trips with sleeping space for up to 10 and outdoor spaces every nature lover will enjoy. The pet-friendly cabin has a lovely deck, a well-equipped kitchen, a spacious yard with fire pits and lake views, and a private dock. Whether you love swimming, fishing, kayaking, hiking through the forest, or making S’mores around the fire, outdoor adventure in Wisconsin’s Northwoods has never been more accessible.
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5. Beechwood Cottage
- Address: Sister Bay, WI
- Size: 2 bedroom, 1 bath
- Price: $170/night
- Amenities: Wifi, AC, washer/dryer, fireplace, screened all-season porch
- Ratings: 4.9 Exceptional
Beechwood Cottage in Sister Bay may be the most charming cabin in Wisconsin and looks like something out of a fairytale, from its gently curved A-frame walls to its spiral staircase to its lush wooded surroundings. Rustic charm is combined with modern mid-century furnishings, high ceilings, and huge picture windows to enjoy the outdoors from the warm, cozy living area. The spacious loft has a queen bed and its own relaxing sitting area with a view, and the enclosed porch has a sofa and dining table to relax and dine surrounded by nature. It almost feels like a treehouse!
6. A-Frame on Horseshoe Lake
- Address: Newton, WI
- Size: 2 bedroom, 1 bath
- Price: $212/night
- Amenities: Wifi, fireplace, BBQ, fire pit, kayaks, rowboat, outdoor furniture
- Ratings: 5.0 Exceptional
With all the cozy feels of a log cabin in the woods but with modern amenities, this A-frame on Horseshoe Lake has earned incredible reviews. Not only is the house lovely, but the wooded surroundings with lake views are just gorgeous and the host provides lots of extras to make the most of it including a large deck, a gas grill, a fire pit, two kayaks, and a rowboat. With two levels of living space, three beds, lake views from the living room, and more, it is ideal for a relaxing family escape. Want to venture out a bit? Explore farther along the shores of Lake Michigan or head just 15 miles up the coast for ice cream sundaes in Two Rivers.
7. Lake Pepin Cottage
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- Address: Stockholm, WI
- Size: 2 bedroom + loft, 1 bath
- Price: $217
- Amenities: Pet-friendly, Wifi, fireplace, outdoor dining, BBQ, AC/heating, private beach, BBQ
- Ratings: 4.9 Exceptional
Sitting right on the beach, this surprisingly spacious cottage sleeps six with two bedrooms and a sleeping loft. The large furnished deck and high ceilings with a full wall of picture windows allow guests to enjoy natural beauty whether inside or out. Some 100 feet of private waterfront space are a perfect jumping-off point to explore everything Lake Pepin and the Mississippi River have to offer, including fishing, swimming, boating, and more. Back at the cottage, there is a wonderfully equipped kitchen, a cozy retro fireplace, and lots of seating space. Find more details by checking out the Lake Pepin Cottage on Vrbo.
Historic Homes for Rent in Wisconsin
When traveling, we love seeking out historic places full of old-fashioned charm and details, but it is not every day that you can stay overnight in a place that takes you back in time. These highly unique places bring history to life with authentic vintage details and a genuine taste of a time gone by.
8. Abby’s Century Old House
- Address: Baraboo, WI
- Size: 4 bedroom, 2 bath
- Price: $468/night
- Amenities: Wifi, AC, washer/dryer, fireplace, BBQ, child’s highchair and crib
- Ratings: No reviews yet
Abby’s Century Farm House was built in 1905. It is full of turn-of-the-century American charm, feels like an old-fashioned bed and breakfast (but it’s private!), and is focused on providing families and groups of up to 12 with everything they need for a fantastic stay. Families with little ones can pack light as the house includes a travel crib, a highchair, a children’s table, toys, and more. Outside, you not only have a grill, fire table, and seating, but access to the Sauk County ATV/UTV trails system - so bring your big toys in summer and enjoy snowshoeing in the winter! This stately home is also close to the Wild Rock Golf Course, Canyon Creek Riding Stables, and Oschner Zoo, among other attractions.
9. The Historic A.C. Carter House
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Stay Overnight At This Spectacularly Unconventional Vacation Home In Wisconsin
- Address: La Crosse, WI
- Size: 3 bedroom (plus futon and air beds), 1 + 1/2 bathroom
- Price: $140/night
- Amenities: Wifi, washer/dryer, AC, pet-friendly
- Ratings: 4.8 Exceptional
The Historic A.C. Carter House is like a living art museum. It is an authentic Victorian-era “gingerbread house” that was nominated to the National Registry of Historic Places es and is listed on the La Crosse historical walking tour. Though fully restored and appointed with modern amenities, it is full of genuine antique furnishings such as ornately carved mahogany and cherry beds from the 1820s and 1850s, a stunning stained glass window, and tons of vintage fixtures. A stay in this historic building whisks you away to the elegance of the 1800s.
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10. 1897 Historic Victorian
- Address: Milwaukee, WI
- Size: 8 bedroom, 3 bath
- Price: $615/night
- Amenities: Wifi, pet-friendly, AC, washer/dryer
- Ratings: 4.9 Exceptional
This spectacular Victorian home is located in one of the top three “Historic Registered” neighborhoods in the USA. Featuring antique fixtures, arched windows, pretty views, hand-sewn quilts, a rec room, multiple fireplaces, a beautiful half-round front porch, and outdoor furniture, the 1897 Historic Victorian sleeps 20 in eight guest rooms - perfect for weddings, family events and gatherings, friends weekends, etc. There are even bicycles available - explore the are with an old-fashioned biking adventure.
Converted Buildings for Rent in Wisconsin
If you are looking for something completely out of the ordinary, skip the boutique hotel and book a truly one-of-a-kind getaway. These unique rentals in Wisconsin may have kitchens and beds and sofas now, but they had a whole other life before this, making them among the most unique places you can stay.
11. Blue Store
- Address: Milwaukee, WI
- Size: 5 bedroom (plus sofa bed), 2 bath
- Price: $358/night
- Amenities: AC, washer/dryer, lake view, custom arcade, party friendly, BBQ
- Ratings: 4.7 Exceptional
Aptly called the Blue Store, this historic building - constructed in 1923 - was, in fact, a neighborhood grocery store in the 1950s. It has been beautifully renovated into a perfect entertainment space with a 70-inch TV, an arcade with over 1100 classic games, a separate family room, a fully stocked kitchen, a 9-foot dining table, and sleeping space for 14. The converted rental is close to Miller Brewing Company, New Berlin Hills Golf Course, Pettit National Ice Center, and more.
12. Devils Lake School House
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- Address: Barbaoo, WI
- Size: 3 bedroom (plus 2 queen beds in living space), 2 bath
- Price: $363/night
- Amenities: Wifi, pet-friendly, AC, fireplace, screened porch, outdoor furniture, games, printer
- Ratings: 4.9 Exceptional
Formerly known as Park View School, this pre-1877 school house is now a stunning vacation rental for up to 12 guests with spacious living and entertainment spaces, furnished with authentic Amish Crafted furnishings. There are even a few remnants of the building's school life such as a wall chalkboard. Devils Lake School House is in an excellent location for hiking and exploring the bluffs around Devil’s Lake, being walking distance from the entrance to Devil’s Lake State Park. It is also close to Tumbled Rock Micro Brewery, downtown Baraboo, Wisconsin Dells, and Devil’s Head Resort for skiing in winter.
13. Historic Calderwood Lodge
- Address: Luck, WI
- Size: 6 bedroom, 3 bath
- Price: $1,099
- Amenities: AC, pet-friendly, BBQ, washer/dryer, RV parking, fire pits,
- Ratings: 5.0 Exceptional
The amazing Historic Calderwood Lodge is another unique rental with a past life. In the 1920s and 1930s, Al Capone, John Dillinger and scores of wealthy patrons parked their Model T’s near the lake and stayed here at what was known as the Old Supper Club. The original 20-seat bar is a one-of-a-kind feature and is complemented by a pool table, 11 flat screen TVs, a massive open floor plan living space and sleeping space for at least 20 guests. Rumor has it that when Prohibition struck, this place still served alcohol, storing it across the lake in secret concrete vaults. How is that for a place with a past? This storied lodge is like having your very own boutique hotel.
Large Group Rentals in Wisconsin
We have already mentioned a couple of great rentals that will accommodate larger groups, but there are a few more of these massive rentals that we just have to share because if you are planning a group event or getaway, there are some truly special properties that will elevate any vacation with family or friends.
14. Lighthouse Waterfront Adventure
- Address: Algoma, WI
- Size: 6 bedroom, 3 + 1/2 bath
- Price: $354/night
- Amenities: Private lake access, AC, pet-friendly, washer/dryer, fire pits, basketball and tennis courts, rec room, kayaks, fire pit, fireplaces, home theater, child/baby supplies, sports equipment, bikes, fishing gear
- Ratings: 4.7 Exceptional
This Lighthouse Waterfront Adventure is a storybook-like mansion on a huge private estate near Door County. It is located just south of Sturgeon Bay directly on the shore of Lake Michigan. Private lake access, an epic game room, a bar room, a theater room, multiple fireplaces, sleeping for 28, tons of natural light, and stunning views from every room, you simply cannot ask for a more lovely place to spend time with a group of friends or family. Outdoor spaces include fire pits with seating, sports courts and equipment, kayaks, winter adventure equipment, fishing gear, and much more.
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15. Big Sky Barnhouse
- Address: Arena, WI
- Size: 6 bedroom, 3 + 1/2 bath
- Price: $661/night
- Amenities: Pool, hot tub, fire pit, mini golf, theater, slide, gym, sauna, pet-friendly, washer/dryer, arcade, game room
- Ratings: No reviews yet
Like the Calderwood Lodge, Big Sky Barnhouse is a historic building and converted rental that has received a great deal of attention nationwide. Formerly a typical Wisconsin dairy barn, this is now an extraordinary 7000-square-foot rental home full of modern luxury and extravagant amenities. Quirky and elegant, guests enjoy indoor mini golf, a spiral tube slide, multiple living spaces, a stunning home theater, a pool, hot tub, sauna, fitness center, office spaces, epic game room, indoor basketball, three decks, and tons of other amenities for a spectacular group vacation just 30 miles west of Madison - essentially a private resort!
16. The Castle Vineyard
- Address: Cleveland, WI
- Size: 4 bedroom, 3 + 1/2 bath
- Price: $754/night
- Amenities: Hot tub, Wifi, AC, theater, fireplace, fire pit, BBQ, pool table, foosball, arcade game, travel crib, child’s highchair, basketball
- Ratings: 5.0 Exceptional
A European-style castle on the Great Lakes? Yes indeed! Sitting majestically on a working vineyard, The Castle Vineyard provides the ultimate luxury to travelers wanting to experience the Tuscan countryside without ever boarding a plane. The magic of the rolling vineyard hills and stone walls of the castle only hint at what awaits inside. A gorgeous piano room features a mini baby grand piano chandelier overhead and a grand piano for musical guests to enjoy. Vintage details like a gas streetlamp from Fort Wayne in the entry, church lights from an 1800s church in Plymouth, a dining table made from a 1914 John Deere plow, and more, add to the elegant country charm. Unmatched amenities include a wine hall, game tables, a video arcade, an incredible home theater, a hot tub, a sauna, an indoor putting green, a state-of-the-art kitchen, and comfortable spaces throughout.
17. Garden of Eden
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- Address: New Berlin, WI
- Size: 6 bedroom, 7 bath
- Price: $1,764/night
- Amenities: Wifi, indoor pool, AC/heating, washer/dryer, fire pit, kayaks, stand-up paddle boards, canoes, BBQ, game room, arcade, baby and toddler supplies
- Ratings: 4.7 Exceptional
Did we leave the most unique rental until last? You be the judge, but the quirkiness of this custom-designed rental, named The Garden of Eden by the host, definitely sets it apart from the rest. Secluded on 17 acres of forest, this one-of-a-kind group rental has to be seen to be believed. Dine together at the stunning dining table with its 16 hand-made custom butterfly chairs. The almost prehistoric jungle-themed great room, indoor koi pond, stone interior walls, quirky murals, indoor stone pool, incredible game room with vintage popcorn maker, and individually designed bedrooms with boutique hotel linens just touch the surface of this unforgettable escape. Outdoors, enjoy a private spring-fed lake with a sandy beach, fire pits with s’mores kits, and various outdoor seating areas, and plenty of water toys.
From tiny living to massive private lodges, there are unique places to stay in Wisconsin that will make your trip unforgettable. Which of these rentals would you love to stay in? Feel like you need a few more options? We’ve got you – check out even more amazing places to stay in Wisconsin.
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More to Explore
Unique Places To Stay In Wisconsin
What are the best unique hotels in Wisconsin?
- Saint Kate Arts Hotel, Milwaukee
- Castle La Cross Bed and Breakfast, La Crosse
- The Edgewater Hotel, Madison
- The Delafield Hotel, Delafield
- The Charmant Hotel, La Cross
- Find out about these unique properties and a few other amazing hotels in this article.
Where are some unique cities and towns in Wisconsin?
If you ask us, every destination in the state has something special to offer! That being said, these are some of the unique cities and towns in Wisconsin that everyone should visit: