Last Updated January 20, 2021 1/20/2021

17 Coolest Airbnbs in Wisconsin

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Wisconsin is most popularly known as being America’s Dairyland. Expect to find an abundance of world-class cheesemakers in this northern state. But nature, skiing and access to two of the Great Lakes adds to the natural appeal. Come to Wisconsin, and experience the city life, then, venture into its breathtaking forests. We found more than a handful of unique and intriguing Airbnbs that will enhance any trip to the Scandinavian-influenced state.

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Beechwood Cottage, Secluded A-Frame - Sister Bay Beechwood Cottage - Secluded A-Frame in Sister Bay
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Beechwood Cottage - Secluded A-Frame in Sister Bay

Beechwood Cottage, Secluded A-Frame - Sister Bay

Stay amongst the trees in Sister Bay. The A-frame cabin has an interesting curve to its architecture, which is evident both from the outside and in. While paneled wood walls add warmth, the kitchen is quite up to date, and the bathroom has a trendy chic theme.

Kodiak on Long Lake - Comstock Kodiak on Long Lake
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Kodiak on Long Lake

Kodiak on Long Lake - Comstock

Taking several pages from the Scandinavian book of design, the brand new cabin is light, yet warm, with clean-cut touches. High ceilings open the space up, and the overall look is completely stunning. Being right on the lake, the views enhance the structure’s beauty.

Off-Grid Inn - Fall Creek Off-Grid Inn - Fall Creek
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Off-Grid Inn - Fall Creek

Off-Grid Inn - Fall Creek

There’s nothing quite like going completely off-grid. Find yourself, or just decompress. Each wooden structure is light and airy, with extra plush bedding. Huge windows bring the outdoors into your super comfy nook.

Springbrook's 1850's Cottage - Burnett Springbrook's 1850's Cottage
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Springbrook's 1850's Cottage

Springbrook's 1850's Cottage - Burnett

Transport back to the 1850s, and stay in this simplistic cottage that still has its original appeal. Keep in mind, things really are like they were in the 1800s in many ways, as there is no running water, and guests will have to use an outhouse. But not just any outhouse, it’s definitely been modernized. Disconnect, reflect, find inner peace.

Tiny on the River - Black River Falls Tiny on the River
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Tiny on the River

Tiny on the River - Black River Falls

Experience tiny living for a few days, while on a scenic river in Wisconsin. Wood flows throughout the interior space, and the fireplace is excellent for snuggling by and enjoying a cup of hot cocoa. Wake up to views from a massive picture window, right beside the bed.

Charming Milkhouse Cottage, Minutes from Madison - Sun Prairie Charming Milkhouse Cottage, minutes from Madison
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Charming Milkhouse Cottage, minutes from Madison

Charming Milkhouse Cottage, Minutes from Madison - Sun Prairie

Welcome to the milk house, literally living up to its name since the 1800s. Designed in a lightly colored, French cottage aesthetic, you’ll feel as if in a totally timeless dimension. On the property, enjoy goats, chickens, and rows of apple and maple trees.

Fancy Fireflies, Charming Studio Cabin - Hayward Fancy Fireflies-Charming studio Cabin in Hayward
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Fancy Fireflies-Charming studio Cabin in Hayward

Fancy Fireflies, Charming Studio Cabin - Hayward

Whether draped in snow or surrounded by vibrant green foliage, the Fireflies cabin is a magical oasis in the woods. Dazzling lights twinkle above the structure, and inside. A basic studio layout is perfect for couples, or that solo traveler looking for solace. Enjoy onsite amenities like a fire pit and grill—the lake isn’t far away either.

Lost Creek Retreat - Pepin Lost Creek Retreat
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Lost Creek Retreat

Lost Creek Retreat - Pepin

When a home is featured in Martha Stewart Living, you know it has that incredible traditional home charm. With touches of country vibes, guests will also literally be next to chicken coops and barns. The best part? The home is enveloped in an apple orchard.

Northwoods Chalet - Bayfield Northwoods Chalet
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Northwoods Chalet

Northwoods Chalet - Bayfield

Cozy up by the fireplace, sit out on the massive screened porch that provides a little protection from the elements and breathe in the silence of the woods. Various trails weave to the shores of Lake Superior. Either summer or winter, this modern rustic escape is ideal.

Life UnContained - Viroqua Life UnContained
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Life UnContained

Life UnContained - Viroqua

See how utterly gorgeous container homes can be! While from the exterior, the structure looks like something that could have just been unloaded from a cargo ship, the inside is traditional, with loads of modern farmhouse attributes. In the yard is a lovely outdoor dining area, that will let you soak up the sun and enjoy a glass of lemonade.

The Plaza Hotel and Apartments - Milwaukee The Plaza Hotel and Apartments
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The Plaza Hotel and Apartments

The Plaza Hotel and Apartments - Milwaukee

Looking for somewhere trendy, yet classic to say in Milwaukee? You found it. Come explore the big city and all of the adventures that come along. Then return to the comfiest beds, and relaxing bathrooms at night.

The Croquet Cabin Cozy - Arbor Vitae The Croquet Cabin Cozy
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The Croquet Cabin Cozy

The Croquet Cabin Cozy - Arbor Vitae

A cobblestone exterior, an interior fireplace, the most intricately precious shutters, and lanterns that add ambient light – this place is an absolute fairytale. When visiting the Northwoods of Wisconsin, the hosts provide a dreamy escape. Perfect for a skiing vacation, or even a summer escape!

Charming Sailboat Stay - Racine Charming Sailboat Stay
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Charming Sailboat Stay

Charming Sailboat Stay - Racine

Not sure you would love the sea life? Give it a test run, while staying on this sailboat that stays stationary in a marina. Experience the gentle rocking at night, while being close to phenomenal restaurants. A pool and other amenities are also at the guest’s disposal.

Chic Loft Surrounded by Nature - Helenville Chic Loft Surrounded by Nature
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Chic Loft Surrounded by Nature

Chic Loft Surrounded by Nature - Helenville

Likely the first thing that will catch your eye in this chic loft is the suspended king-size bed! Many of the newly remodeled features have been handcrafted, giving it an intricate appeal. Located in between Madison and Milwaukee, you’ll be in the country, but still not terribly far from neat sites. Soak up plenty of sun via the skylights!

Cozy Camp Near Lake Michigan and State Parks - Cedar Grove Cozy Camp Near Lake Michigan and State Parks
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Cozy Camp Near Lake Michigan and State Parks

Cozy Camp Near Lake Michigan and State Parks - Cedar Grove

Close to the coast of Lake Michigan, this basic yet extremely welcoming abode has a kitchen, living area and snug sleeping loft accessible by ladder. However, there is not any running water. Biking trails weave through the property, and a fire pit area is surrounded by comfortable seating.

Peaceful Bayside Cottage - Wautoma Peaceful Bayside Cottage
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Peaceful Bayside Cottage

Peaceful Bayside Cottage - Wautoma

Bring the family to this relaxing cottage with ample space and a fantastic kitchen. But most of the time will likely be spent outside, in the yard, peering outward toward the water. Folks love to come here to fish, kayak and do all sorts of other outdoor activities.

Repurposed Turn of the Century Silo - Helenville Repurposed Turn of the Century Silo
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Repurposed Turn of the Century Silo

Repurposed Turn of the Century Silo - Helenville

Loads of history lie within this old turn of the century silo. Foliage envelopes the structure, adding to its storybook allure and beauty. Inside remains all of the old charms, and it is completely romantic.

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