Best Cabins and Airbnb Rentals in Wisconsin
When the travel pace slows down and we’re not embarking on major international journeys, we’re busy plotting quick weekend escapes to cabins and unique vacation rentals in Wisconsin.
The Badger State’s proximity to Chicago makes it a perfect destination for an easy getaway. Over the last few years, the vacation rental landscape there has become increasingly diverse. We’ve witnessed a surge of beautifully designed cabins and homes appearing on platforms like Airbnb and Vrbo.
In this blog post, we’ve gathered some of the most beautiful Wisconsin cabins we’ve had the pleasure of staying in. Be sure to bookmark this post, as we’re looking forward to updating it as we visit more places!
Kodiak on Long Lake in Comstock, WI
Driving distance: Approximately 5 hours and 20 minutes. Since it’s a bit further from Chicago, we recommend spending at least 3 nights.
Starting off strong with one of the most beautiful properties in Wisconsin—Kodiak on Long Lake, a modern Scandinavian cabin in Comstock, Wisconsin. The cabin is tucked away in a lush forest with direct access to a small lake, and the surrounding area feels very secluded and private. The interior design is minimalistic, yet still feels inviting and cozy.
What makes this cabin special are the floor-to-ceiling windows that flood the main living room, dining room, and kitchen area with natural light even on dismal days! These windows overlook the lake, which provides a peaceful backdrop to enjoy no matter the season.
We visited The Kodiak right after an intense winter storm that transformed the cabin’s surroundings into a winter wonderland. In weather conditions like that, The Kodiak is a perfect place to spend time snuggling by the fireplace, playing games, and making delicious meals in the fully equipped kitchen.
Summer is also a great time to visit as The Kodiak offers kayaks and paddle boards, as well as opporunities to swim in the lake, lounge in the hammock, and much more.
Hayward Haus in Hayward, WI
Driving distance from Chicago: Approximately 6 hours. We recommend staying for at least 3 nights.
Hayward Haus is another stylish Scandinavian cabin in Wisconsin we can’t get enough of! Located a short distance from Hayward, Wisconsin, on Upper Twin Lake, it offers a peaceful retreat in beautiful natural surroundings.
Cassidy, the owner, really put his heart into decorating the cabin with simple, well-crafted furniture that complements the minimalist aesthetic. A special touch is added by the houseplants thriving in the space, all thanks to the massive windows.
Hayward Haus is a year-round destination, perfect for both summer and winter getaways. In warmer weather, you can enjoy activities like hiking, fishing, and kayaking. When the snow falls, the area transforms into a winter wonderland, offering opportunities for snowshoeing and cross-country skiing.
Plus, when it’s chilly out, you have everything you need to stay cozy inside: a fireplace, blankets, books, games, and candles strategically placed throughout to add warmth and ambiance.
The Asher Field & Lake in Belgium, WI
Driving distance from Chicago: 2 hours.
Fancy spending a weekend in a house overlooking Lake Michigan? The Asher, one of two thoughtfully designed properties in Belgium, Wisconsin, owned by the design and hospitality firm Field & Lake, might be just the place for you!
The Asher is a stunning property that combines traditional and modern styles in its design. You’ll see vintage furniture and wall art mixed with modern furniture pieces and high-end amenities.
With three bedrooms, the house can accommodate up to 8 guests. The open-concept ground floor includes a spacious, fully-equipped kitchen, dining area, and living room with a gas fireplace. The house’s special feature: east-facing floor-to-ceiling windows overlooking Lake Michigan. Looking out these windows is better than watching TV; you can enjoy beautiful views of the lake without even having to step outside!
Both upstairs bedrooms have access to a balcony overlooking the lake. Imagine sleeping with the door open and listening to the sound of waves!
On the outdoor patio, you’ll find a brand new 8-person hot tub. A few steps further toward the lake there’s a fire pit for those cozy stargazing nights with s’mores and hot cocoa. Firewood is provided by the property.
The Asher provides a peaceful retreat year-round. In fact, it’s so beautiful that you might never want to leave!
Lake Cabin in Kohler, WI
Driving distance from Chicago: 2 hours
The Lake Cabin at the American Club in Kohler, Wisconsin, offers a stunning lakeside retreat just 2 hours from Chicago. Decorated with cozy, cottage-style charm, the cabin has two bedrooms and two bathrooms, accommodating up to six guests. It’s perfect for get-togethers with family and friends.
The fully-equipped kitchen, coupled with the American Club’s grocery delivery service, ensures you have all you need without the hassle of grocery shopping. Because the cabin is part of the American Club resort, guests have access to fine dining, a spa, a fitness center, and more!
Nestled in a secluded area surrounded by trees and the beauty of Lake Michigan, the Lake Cabin offers a serene escape. You can even watch the sunrise over the lake from inside! It’s an ideal place to disconnect, rest, and recharge.
Our winter stay by Lake Michigan was truly special, and we can only imagine the beauty of a summer getaway there! We’re definitely planning to return.
the glass house on Birch Bluff in Door County, wi
Driving distance from Chicago: around 4 hours
If you’re planning a visit to Door County, Wisconsin, you should stay at the charming Glass House on Birch Bluff, named in honor of Fredrica “Fritzie” Glass, the artist, teacher, and writer who built the cottage in 1969.
This cottage is a Door County gem! It’s quaint and cozy with a thoughtfully designed interior. You’ll find little things like fresh flowers, houseplants, books, and comfy spots for reading all around. You’re meant to feel right at home.
The cottage’s beautiful kitchen deserves a special mention. It’s equipped with all the essentials, making the cooking experience easy and enjoyable.
The Glass House sits on three gorgeous acres in Fish Creek surrounded by trees. The area is quiet and secluded, but still close to the main attractions in Door County, including many hiking trails. It provides a great home base to explore the area.
Whether you like going out on adventures or staying in to cook, play board games, and sit by the fire, this Airbnb in Door County, Wisconsin is great!
Pepin Forest Treehouse in Pepin, WI
Driving distance from Chicago: Approximately 5 hours and 30 minutes. Since it’s a bit further from Chicago, we recommend spending at least 3 nights.
This is a brand-new cabin built in 2023 in Pepin, Wisconsin. As you may have guessed, the cabin was constructed in the treehouse style, elevated from the ground with a big tree trunk in the center running from floor to ceiling.
Pepin Forest Treehouse can accommodate up to 4 people, but it’s probably most comfortable for a couple. There’s a sleeper sofa and a twin bed under the stairs on the first floor, and a cozy lofted bedroom with a queen bed upstairs. The cabin itself feels compact and cozy, and it’s ideal for a romantic getaway!
We visited Pepin Forest Treehouse in frigid winter weather, so we spent most of our time inside enjoying all the amenities the cabin has to offer, including its well-curated collection of books and games, a smart TV, and an outdoor hot tub. One of our favorite activities was birdwatching. Pepin Forest Treehouse is surrounded by trees, and you can see lots of birds playing around through the big windows.
The treehouse features a sleek and modern design, effortlessly combining luxury amenities with natural elements like wooden branches. Decorated in soothing, neutral colors reminiscent of a forest—think greens, beiges, and browns—the ambiance is just perfect. Large windows frame views of the surrounding trees, immersing you in nature. Pepin Forest Treehouse is your go-to for a relaxing getaway, and the drive from Chicago is worth it!
Elkhart A-frame in Elkhart Lake, WI
Driving distance from Chicago: 2 hours
Do you like A-frame cabins as much as we do? Then be excited about this relatively new A-frame rental in Elkhart Lake, Wisconsin!
Built in the 1970s, this unique cabin got a makeover with a modern Scandinavian style. The cabin is best suited for 2-3 adults but can accommodate up to 5 people.
The cabin looks mid-century modern, yet cozy with a staircase connecting the two floors. Upstairs, there’s a bedroom with a queen bed and a TV loft area. Downstairs, you’ll find a twin bedroom, living room, bathroom, and a kitchen with a dining nook. Outside, there’s a wraparound deck and a fire pit in the backyard.
The Elkhart A-frame is perfect for those seeking a quiet retreat while also being close to everything exciting. The house stands on three private acres surrounded by trees, just a mile from Elkhart Lake, Road America, and golf courses.
Even if you decide to spend the majority of your time at the cabin, there is plenty to do. You’ll find books, board games, and a smart TV to keep you entertained.
Camp Wandawega Hillhouse in Elkhorn, WI
Driving distance from Chicago: 2 hours
Introducing The Hillhouse, a charming rental property in Elkhorn, Wisconsin. Originally a cozy summer cabin dating back to 1930, it has undergone a recent facelift. While maintaining its historic charm, the house now offers modern comforts and amenities.
This two-story gem accommodates up to 6 people, featuring 3 bedrooms, a fully-equipped kitchen, a roomy living area with a fireplace, and a sprawling deck on the main level.
Step inside, and you’ll be greeted by a delightful blend of vintage decor, unique art pieces, and standout furniture. The living room’s fireplace promises warmth and a homey feel, perfect for chilly winter days.
As part of Camp Wandawega, The Hillhouse grants guests access to an array of amenities, including a beach on serene Lake Wandawega, inviting fire pits, a whimsical treehouse, and more. Surrounded by nature, the house’s proximity to Chicago makes it an ideal spot for a weekend getaway with friends or family.
