17 Quirky and Cool Vacation Rentals in Wisconsin to Book ASAP

Looking for a comfortable accommodation for a weekend getaway? There are plenty of unique places to stay in Wisconsin that will make you want to book an entire week in the name of total relaxation. Whether you're booking a romantic retreat for you and your significant other, planning a quick trip for the family, or hoping to get some alone time out in nature, there's a house rental for almost every type of traveler in the Badger State.

Whether you're looking for a quirky experience, like a covered wagon camping adventure, or something a little more luxurious (say, a slow-travel cabin retreat), you'll find a perfect vacation rental match out of the following 17 listings. Stay out in the woods, by the water, or in the state's historic districts, fully immersing yourself in what beautiful Wisconsin has to offer. Without further ado, let’s check out some of the coolest and most unique places to stay in Wisconsin.

Tiny Home Rentals in Wisconsin That Make Perfect Weekend Escapes

There's no denying the uniqueness of tiny homes, with all the comforts of a house tucked perfectly into a compact space. The following three vacation rentals have far more to offer than meets the eye, and are really cool places to stay in Wisconsin. Find solace along the Black River, near Lake Superior, or in the woods of Wisconsin Dells.

1. Tiny House on the River, Black River Falls

• Address: Black River Falls, WI
• Size: 1 bedroom, 1 bath
• Price: $223/night
• Amenities: River view, Heating/AC, indoor fireplace, BBQ, Wifi, outdoor fire pit, EV charger
• Ratings: 4.9/5 stars

Sitting right over the Black River in a quiet neighborhood, this adorable Tiny House on the River offers a fully stocked kitchen, plush furnishings (including a comfy daybed on the screened porch), a wall of windows to soak up river views in any season, and everything you need for the perfect getaway. It's located in a quiet neighborhood, in the backyard of a main house, but still offers lots of seclusion and privacy for those in need of an escape. Spend the day sitting by the fire, fishing on the river, or driving minutes toward downtown Black River Falls to enjoy quaint shops, restaurants, walking trails, parks, and more.

Whether you're hoping for a cozy winter getaway or a fun summer vacation vibe, this cabin is available year-round and is a great acommodation for all seasons.

2. Blue Belle Tiny House Dells Adventure, Grand Marsh

• Address: Grand Marsh, WI
• Size: 2 bedroom (plus living room futon), 1 bath
• Price: $153/night (a two-night minimum booking is required)
• Amenities: Lake access, Wifi, crib, pet-friendly, AC, heating, BBQ, fire pit, patio
• Ratings: 4.56/5 stars

Enjoy tiny living surrounded by nature at Blue Belle Tiny House—a charming 400-square-foot home situated on a nearly 100-acre property with a stunning lake and several trails to hike and explore. Despite its size, the home sleeps six guests, with a queen bed, two twin beds, and a pull-out sofa in the living room. It's ideal for families who love outdoor adventures, plus it's close to local attractions like Chula Vista Waterpark, Pirate's Cove Adventure Golf, and Timber Falls Adventure Park. And with it less than 20 minutes from downtown Wisconsin Dells, you'll still feel connected to civilization.

The only downsides to this cute powder blue home? There's no in-unit washer and dryer, so you'll have to go to a laundromat nearby. You'll also need to bring your own drinking water, as the property only has well water suitable for bathing and dishwashing.

3. Lupine Landing, Cornucopia

• Address: Cornucopia, WI
• Size: 2 bedroom, 1 bath
• Price: $342/night (a two-night minimum booking is required)
• Amenities: Waterfront, indoor fireplace, heating, Wifi, BBQ, board games
• Ratings: 4.9/5 stars

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 home is situated on Spirit Point, a peninsula on Lake Superior and Siskiwit Bay, offering spectacular waterfront views. Take in the scenery from the fully screened-in porch or from the plush couch inside, next to big windows overlooking the outdoors. The vaulted ceilings, fully stocked kitchen (it even has a popcorn maker!), and ideal location will make you fall in love. We also highly recommend exploring nearby beaches while you're there, including Cornucopia Beach, Meyers Beach, Port Wing, and the Apostle Islands.

Because this home does not have central air conditioning, it can get hot in the summertime. So if that's not your thing, plan a staycation during the fall or spring when the weather is cooler. Also, outdoor fires are not allowed on this property; however, you can use the propane-type fire table outside.

Rustic A-Frame Rentals in Wisconsin

Something about an A-frame home takes the appeal of a cozy cabin to a whole new level. Whether you want to feel like you're nestled high in the treetops or on a beachside summer vacation, these homes are certainly ideal. From spacious cottages near Lake Pepin to enchantingly romantic cabins in Sister Bay, here are four worth booking ASAP.

4. A-Frame Cabin With Private Boat Dock, Butternut

• Address: Butternut, WI
• Size: 3 bedroom (plus sofa bed), 1 bath
• Price: $247/night (two-night minimum booking required)
• Amenities: Washer/dryer, AC/heater, Wifi, fireplace, two fire pits, private boat dock, pet-friendly
• Ratings: 4.8/5 stars

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.

While you can visit this cozy waterfront cabin any time of year, we highly recommend booking in the summer so you can go swimming and boating on Butternut Lake. You can even park your trailer here, too, if you need a place to rest during a Wisconsin road trip. And if you're hoping to travel with friends? Contact the hosts to book another 2-bedroom property down the street.

5. Beechwood Cottage, Sister Bay

• Address: Sister Bay, WI
• Size: 2 bedroom, 1 bath
• Price: $478/night (two-night minimum booking required)
• Amenities: Wifi, AC/heating, washer/dryer, fireplace, record player, pack 'n play crib, children's toys, screened all-season porch, outdoor furniture, BBQ grill, beach essentials
• Ratings: 5/5 stars

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 getaway in Wisconsin.

Spend the day exploring the 1.6 acres of woods on the property, or take a five-minute drive down to Ellison Bay to enjoy the water. This house is considered a rare find on Airbnb, meaning it books up quickly. So if you're considering visiting a "guest favorite" in the Badger State, secure your vacation dates soon!

6. Lakefront A-Frame, Merrimac

• Address: Merrimac, WI
• Size: 4 bedrooms, 2 baths
• Price: $712/night (two-night minimum booking required)
• Amenities: Lake view, waterfront, private dock, Wifi, washer/dryer, pool table, game console, Bluetooth sound system, children's books and toys, AC/heating, indoor fireplace, private backyard, fire pit, outdoor furniture, BBQ grill, kayaks, sun loungers, beach essentials, cleaning available during stay
• Ratings: 4.85/5 stars

If you're looking for a spacious home for a family summer vacation, this lakefront A-frame in Merrimac is the perfect spot. It easily sleeps up to eight guests and has all the modern amenities one could hope for. Spend time admiring the gorgeous views of Lake Wisconsin from the spacious windows or outside on the private dock. Go kayaking or swimming and then cook a delicious dinner with the state-of-the-art kitchen and outdoor grill. After a long day of activities, curl up by the fire, or play pool and video games with the kids.

This cozy rustic cabin is super kid-friendly; it even has two sets of twin beds and children's books and toys, perfect for kiddos. If you come in the wintertime, drive 15 minutes to Devil's Head Ski Resort. Or go for a day of shopping in Madison or Wisconsin Dells, just 45 minutes away.

7. Lake Pepin Cottage, Stockholm

• Address: Stockholm, WI
• Size: 2 bedroom + loft, 1 bath
• Price: $429/night (two-night minimum booking is required)
• Amenities: Private beach access, beachfront, pet-friendly, Wifi, fireplace, outdoor dining, BBQ, AC/heating,
• Ratings: 4.93/5 stars

Lake Pepin Cottage in Stockholm is right on its own private beach, and despite its small stature, it's surprisingly spacious, sleeping up to six guests in its two bedrooms and upstairs loft. The large furnished deck, high ceilings, and full wall of picture windows allow guests to enjoy natural beauty, whether inside or out. Once you arrive, head right out to the 100 feet of private waterfront space, where you can enjoy fishing, swimming, and boating along the gorgeous Lake Pepin and Mississippi River.

After a day outdoors, head back inside for a cozy dinner in the wonderfully equipped kitchen, followed by a nightcap near the warm fireplace. Be sure to venture during your stay, too. Stockholm has a really charming shopping and dining scene, as well as Villa Bellezza for wine tasting. Book a stay any time of year—just note it fills up fast. So plan ahead!

Historic Homes for Rent in Wisconsin With Charm

One of the most popular things to do while traveling is visiting historic places that take you back in time. But it's not every day that you can actually stay in these places, too. From Civil War-era homes to ornate Victorian homes, there are plenty of beautiful places to stay in Wisconsin with a notable past. Here are three of our favorite places to book a stay, in the well-established neighborhoods of Baraboo, Milwaukee, and La Crosse.

8. The Rest Is History: A Whimsical Victorian Escape, Baraboo

• Address: Baraboo, WI
• Size: 5 bedrooms, 5 baths
• Price: $440/night (two-night minimum booking is required)
• Amenities: Wifi, AC, washer/dryer, movie theater, board games, AC/heating, indoor fireplace, portable fans, outdoor furniture, EV charger, long-term stays allowed
• Ratings: 4/5 stars

This whimsical Victorian home may look like it's stuck in the past, but the interior has been upgraded with all the modern luxuries you need. Families and large groups will love this five-bedroom, five-bathroom historical home, with plenty of room to gather and enjoy quality time together. Guests will enjoy cozy sitting rooms, a wraparound porch swing out front, and even a private movie theater room with a popcorn station. The warm, plush interiors make it an ideal autumn or winter escape. It almost feels like it was once a historic inn in Wisconsin.

After spending some time making meals, watching movies, and resting at this charming home, walk over to downtown Baraboo. It's just two blocks away and boasts delicious restaurants and cafes, and quaint boutique shops. If nature explorations are more your vibe, the home is also minutes away from Devil's Lake and Wisconsin Dells.

9. Historic Carter House-Rivertown Romance, La Crosse

• Address: La Crosse, WI
• Size: 3 bedroom (plus futon and air beds), 1.5 baths
• Price: $169/night (two-night minimum booking required)
• Amenities: Wifi, washer/dryer, AC, pet-friendly
• Ratings: 4.8 Exceptional

The Historic A.C. Carter House is like a living art museum. It was first owned by Civil War veteran, merchant, and patent medicine man, Amos Claude Carter, and his family in the 1880s. But now, the Victorian-era "gingerbread house" is a historical landmark. It was even nominated for the National Register of Historic Places in 1986, and is a must-see spot along La Crosse's historical walking tour.

Despite being fully restored and appointed with modern amenities, the Carter House boasts 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. History buffs will adore how this home whisks guests away to the elegance of the 1800s.

10. Upper East Side Victorian With 9 Bedrooms, Milwaukee

• Address: Milwaukee, WI
• Size: 9 bedrooms, 3 baths
• Price: $1178/night (two-night minimum booking is required)
• Amenities: Wifi, pet-friendly, AC/heating, indoor fireplace, washer/dryer, TV, piano, crib, pack 'n play, children's toys and books, high chair, private backyard, BBQ grill, long-term stays allowed, early luggage dropoff allowed
• Ratings: 4.95/5 stars

This Victorian Home in Milwaukee is located in one of the top three "Historic Registered" neighborhoods in the U.S. Built in 1897, this spectacular mansion on the Upper East Side features antique fixtures, arched windows, stunning views, hand-sewn quilts, a rec room, multiple fireplaces, a beautiful half-round front porch, and a furnished outdoor area to enjoy. You can sleep up to 20 guests here(!), so it's perfect for weddings, family events and gatherings, reunions, and more.

So many luxurious activities await you when staying here. Enjoy a boat day at Lake Michigan, play a round of golf or tennis at the nearby Lake Park, or spend a day at Bradford Beach—a hidden gem with soft sand. You could even use the bicycles on the property to explore the historic neighborhood.

Converted Buildings in Wisconsin Perfect for Vacation

If you are looking for something completely out of the ordinary, skip the boutique hotel and book a truly one-of-a-kind getaway. From a caboose hotel in Wisconsin to stores-turned-vacation homes, these unique rentals may have kitchens and beds and sofas now, but they had a whole other life before this, making them among the coolest places you can stay.

11. Blue Store, Milwaukee

• Address: Milwaukee, WI
• Size: 5 bedrooms (plus sofa bed), 2 baths
• Price: $348/night (two-night minimum booking required)
• Amenities: Golf course view, garden view, lake access, window AC units, radiant heating, washer/dryer, custom arcade, travel crib, party friendly, BBQ
• Ratings: 4.7/5 stars

Aptly called the Blue Store, this historic building—constructed in 1923—was, in fact, a neighborhood grocery store in the 1950s. The 2,000-square-foot space 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. It's a fantastic home for family or friend vacations, or any large group in need of a fun place to stay.

After exploring all the fun amenities inside the home, head outside to enjoy the backyard, where cornhole, outdoor furniture, and a grill—perfect for a summer barbecue. The home is also close to Miller Brewing Company, New Berlin Hills Golf Course, Pettit National Ice Center, and more. If you're not sure what time of year you'd like to visit, check out the booking's seasonal discounts on Airbnb.

12. Devils Lake Schoolhouse, Baraboo

• Address: Baraboo, WI
• Size: 4 bedrooms (plus 2 queen beds in living space), 2 baths
• Price: $533/night (three-night minimum booking required)
• Amenities: Lake access, wifi, washer, sound system, AC/heating, travel crib (available upon request), fireplace, screened porch, outdoor furniture, fire pit, games, BBQ grill, outdoor kitchen, luggage dropoff allowed, pet-friendly
• Ratings: 4.9 Exceptional

If you've ever wondered what it could be like to stay in an old schoolhouse, now's your chance. Devil's Lake Schoolhouse in Baraboo is a one-of-a-kind vacation rental, with plenty of classic charm and modern amenities. The red house, which was built in 1877, sleeps up to 12 guests and has spacious living and entertainment spaces. Each room is furnished with authentic Amish-crafted decor, and even some remnants of the building's old life, including a chalkboard.

After you've taken in the nostalgic charm of this unique rental, head outdoors. The home is close to hiking trails, the North Shore Beach of Devil's Lake, and the rolling bluffs of Devil's Lake State Park. After a few hours in the sunshine, grab a drink at Tumbled Rock Micro Brewery in downtown Baraboo or a restaurant near the Wisconsin Dells. If you're visiting in summer, the home is near Devil's Head Ski Resort, too. Airbnb says it's a rare find—book soon!

13. Historic Calderwood Lodge, Luck

• Address: Luck, WI
• Size: 7 bedrooms, 4 baths
• Price: $1,825/night
• Amenities: Beach access, washer, pool table, board games, AC/heating, Wifi, patio, fire pit, outdoor furniture, BBQ grill, beach essentials, boat slip, RV parking, pet-friendly
• Ratings: 5/5 stars

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 Ts 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.

When you're not cozied up indoors during the winter, head out to Bone Lake for swimming and fishing in the summer. Also, you can contact the host if you'd like to host a reunion, large gathering, or party here; while parties aren't generally permitted, you can get permission in advance for special occasions.

Spacious Wisconsin Rentals for Large Groups

We've already mentioned a few amazing rentals to accommodate larger family or friend groups. But the following four estates are massive and can perfectly handle group events or getaways. The activity possibilities, both inside and outside, are almost endless at these large rentals. While they're close to stunning nature and charming towns, you won't even feel like you need them to stay entertained.

14. Door County Area Waterfront Estate, Algoma

• Address: Algoma, WI
• Size: 6 bedrooms (20 beds), 3.5 baths
• Price: $1,387/night (two-night minimum booking required)
• Amenities: Private lake access, beachfront, garden view, AC/heating, 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, outdoor playground, BBQ grill, beach essentials, long-term stays allowed
• Ratings: 4.8/5 stars

This Door County Area Waterfront Estate is a storybook-like mansion on a huge private estate near Algoma. It's located just south of Sturgeon Bay, directly on the shore of Lake Michigan. Families, corporate retreats, or large gatherings can find just about anything they desire here, including private lake access, an epic game room, a bar room, a theater room, multiple fireplaces, and stunning views from every room. It even has a little lighthouse in the backyard! You can sleep up to 28 guests in this mega home... and never run out of things to do.

Start by taking the complimentary kayaks and fishing gear on the lake, or sunbathe on the private pebble beach right outside the door. Kids will love playing a game of basketball or tennis on the private court or running around the outdoor playground. After time outdoors, head inside for meals in the spacious kitchen, watch a movie, or play some pool in the game room. If you're visiting in winter, you can even use complimentary gear like snowshoes and sleds!

15. Big Sky Barnhouse, Arena

• Address: Arena, WI
• Size: 6 bedrooms, 3.5 baths
• Price: $2,146/night (two-night minimum booking required)
• Amenities: River view, valley view, washer/dryer, exercise equipment, ping pong table, pool table, mini golf course, movie theater, arcade games, children's books and toys, high chair, outdoor playground, AC/heating, Wifi, private patio and balcony, fire pit, BBQ grill, outdoor furniture, private pool and hot tub, private sauna, pets allowed, luggage dropoff allowed
• Ratings: 4.79/5 stars

Similar to Calderwood Lodge, Big Sky Barnhouse is a historic building turned outstanding vacation rental. It's so popular, in fact, that it's received a great deal of national attention. Formerly a typical Wisconsin dairy barn, this gorgeous 7,000-square-foot rental is full of modern luxury and extravagant amenities. Quirky and elegant, guests can enjoy indoor mini golf, a spiral tube slide, an indoor playground, private pool and hot tub, a stunning home theater, fitness center, epic game room, tiki bar... we could go on for days. Between all the super fun things to do and the stunning natural scenery, Big Sky Barnhouse is essentially a private resort.

Invite large groups to this vacation dream home just 30 miles west of Madison and learn what it's like to live in absolute luxury. It's ideal for wedding guests, bachelor/bachelorette parties, corporate retreats, or family reunions. You won't even need to leave the property, but if you do, there's plenty to do nearby, too!

16. The Castle Vineyard, Cleveland

• Address: Cleveland, WI
• Size: 4 bedrooms, 3.5 baths
• Price: $1,298/night (two-night minimum booking required)
• Amenities: Garden view, vineyard view, washer/dryer, piano, record player, sound system, game console, pool table, arcade games, movie theater, AC/heating, Wifi, fireplace, fire pit, BBQ, travel crib, child’s highchair, basketball, private hot tub, private sauna
• Ratings: 4.99/5 stars

A European-style castle on the Great Lakes? Yes, please! 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 hints at what awaits inside. A gorgeous piano room features a mini baby grand piano, a 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. You'll want for nothing at this elegant vineyard escape. It's one of the most wishlisted Airbnbs in the world!

17. Garden of Eden, New Berlin

• Address: New Berlin, WI
• Size: 6 bedrooms, 7 baths
• Price: $2,625/night (two-night minimum booking required)
• Amenities: Private beach access, waterfront, Wifi, indoor pool, private hot tub, AC/heating, washer/dryer, fire pit, kayaks, stand-up paddle boards, canoes, BBQ grill, game room, pool table, Bluetooth sound system, outdoor furniture, baby and toddler supplies
• Ratings: 4.71/5 stars

Did we leave the most unique rental for last? You be the judge! 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. Enjoy a meal 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, various outdoor seating areas, and plenty of water toys. It may seem out of the box, but trust us: You'll appreciate every attention to detail the hosts put into this incredible home.

Which of these rentals would you love to stay in? From tiny living to massive private lodges, there are unique places to stay in Wisconsin that will make your trip unforgettable. Feel like you need a few more options? We’ve got you. Check out even more amazing places to stay in Wisconsin.