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10 Unique Places To Stay In Wisconsin In Winter

A great guide to the most unique places to stay in Wisconsin in Winter for a magical holiday

Welcome to the winter wonderland of Wisconsin, where the snow-covered landscapes and frosty air set the stage for a magical getaway. 

If you’re seeking a winter escape with a touch of uniqueness, you’re in for a treat. In this blog post, I’ll be your guide to some of the most extraordinary and cozy cabins in Wisconsin that promise not just a stay, but an unforgettable experience. 

You’ll find a variety of unique places to stay in Wisconsin in winter that will make your getaway truly special. 

Join me as I explore the distinctive charm of these accommodations and discover the hidden gems that make winter in Wisconsin a season to remember.

a pin with a cabin in winter at one of the most unique places to stay in Wisconsin in Winter.

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1. The Turtle Cottage – Rice Lake

cozy living room with sofa, wooden furniture and kitchen at The Turtle Cottage in Rice Lake, Wisconsin
Courtesy of VRBO

The Turtle Cottage can easily be one of the most unique places to stay in Wisconsin in Winter.

When I stepped inside, I was immediately struck by the vaulted ceiling, giving me the sense that I was inside a real turtle shell. 

The kitchen was fully updated and offered all the amenities I needed to make a delicious meal. I was pleasantly surprised to find free WiFi and air conditioning in the cottage – what a treat! 

The outdoor space was truly exceptional, complete with a barbecue grill, a lakeside deck, and a stunning Tuscobia Lake view. 

This intimate space has everything you need for an unforgettable adventure in Wisconsin, making this cabin one of the best winter cabins in Wisconsin.

2. 1954 Rail Road Caboose Cabin with Relaxing Hot Tub – Aspen

hot tub with view of the 1954 Rail Road Caboose Cabin with Relaxing Hot Tub in Aspen, Wisconsin
Courtesy of VRBO

As I immersed myself in the warm bubbles of the hot tub, I couldn’t help but feel grateful for stumbling upon this unique cabin. 

The 1954 Rail Road Caboose Cabin offered everything I could ask for – a relaxing hot tub, free WiFi, air conditioning, and a gas fireplace to keep me cozy. 

The updated kitchen and new bath added to the luxurious ambiance, not to mention the outdoor space. 

And, best of all, my furry companion was welcomed – it’s pet-friendly! Located on five wooded acres just four miles from the Mississippi River, this cabin is the perfect destination for romantic winter getaways in Wisconsin. 

Not only was my stay incredibly comfortable, but I also enjoyed a peaceful stroll to the nearby trout fishing spot. All in all, I can’t imagine ever staying anywhere else for my winter escapes.

3. Renovated Dairy Barn – Briggsville

garden at the Renovated Dairy Barn in Briggsville, Wisconsin
Courtesy of VRBO

Upon my recent trip to Wisconsin, I had the pleasure of staying in an amazing renovated 70-year-old dairy barn located just footsteps away from the sparkling waters of Mason Lake in Briggsville. 

From rustic furniture, farm decor and antiques, to a spacious deck and cozy fire pit, every detail of the barn has been thoughtfully curated to create a charming and inviting atmosphere. 

What’s more, the barn boasts an open kitchen and living room concept, with three levels of living space to explore. 

As I spent my days lounging in the barn’s comfortable quarters and admiring its unique character, I couldn’t help but feel grateful for the opportunity to experience such a distinctive and one-of-a-kind place to stay. 

And if I ever found myself hungry or in need of some entertainment, I was delighted to find that the charming restaurants of Briggsville were only a few short minutes away. 

Truly, this space is a gem among unique places to stay in Wisconsin and I just had to add it to the list of the most rustic cabin rentals in Wisconsin.

4. The Lighthouse – Algoma

exterior of the Lighthouse in Algoma, Wisconsin
Courtesy of VRBO

The Lighthouse in Algoma is the ultimate waterfront adventure destination in Wisconsin. When I arrived, I was amazed by the stunning 265 feet of waterfrontage and the private pebble beach on-site. 

The lighthouse was completely custom-built with a charming nautical theme and had five decks with water views from all of the rooms. 

The spacious 6000 sq ft living space and 6 bedrooms made it the perfect place for a group retreat or family vacation. 

What’s more, with a capacity to sleep 28 people, there is more than enough room for everyone at one of the best lake cabins in Wisconsin.   

Located on 2.5 acres of private and secluded land, the Lighthouse in Algoma is just 14 minutes from Sturgeon Bay, making it one of the best places to go in Wisconsin in the winter.

5. Clarance Cottage in Prairie Style – Mt Horeb

Clarance Cottage in Prairie Style in Mt Horeb with garden and grounds in Wisconsin
Courtesy of VRBO

As a lover of architecture and cozy cabins in Wisconsin, I couldn’t resist the charm of the Clarance Gonstead Guest Cottage. 

This beautiful stone and tidewater cypress cottage is a prime example of the iconic Prairie Style made famous by Frank Lloyd Wright, and its sleek lines and natural materials had me enchanted from the moment I arrived. 

But the real highlight of my trip was exploring the hiking and biking trails nearby, followed by a leisurely skate at the outdoor rink just a few blocks away. 

And with a fully equipped gym and free WiFi, I could stay active and connected even when snowed in. 

I can’t imagine a better Wisconsin winter getaway than the Clarance Gonstead Guest Cottage.

6. Treehouse at Plum Bottom – Egg Harbor

exterior of the Treehouse at Plum Bottom in Egg Harbor, Wisconsin
Courtesy of VRBO

The Treehouse at Plum Bottom is one of the most unique rentals in Wisconsin. Located amidst the rolling prairies and woods of Plum Bottom, this rental sits on 20 acres of land, providing ample space to explore and unwind. 

The treehouse is a cozy retreat with a full kitchen, living room, and dining room, complete with Internet and satellite cable TV. 

But the real highlight of this rental is the spacious 1 bedroom loft above the trees, giving you a birds-eye view of the gardens and walking paths of Plum Bottom Gallery. 

It’s hard not to feel completely immersed in nature when surrounded by the lush greenery and chirping birds. 

So if you’re looking for one-of-a-kind Door County cabins on Lake Michigan, the Treehouse at Plum Bottom is just what you need. 

7. Frank Lloyd Wright-Designed House – Milwaukee

bedroom with natural light at Frank Lloyd Wright-Designed House in Milwaukee, Wisconsin
Courtesy of VRBO

Walking through this Frank Lloyd Wright-designed house in Milwaukee is like stepping into a different world. 

The Stickley sofa and other built-in furniture pieces that he has designed fit so perfectly with the entire aesthetic of the house. 

The natural fireplace that illuminates the room adds a warmth unmatched by any other heating system. 

The vintage Danish-designed Poggenpohl kitchen is the perfect place to cook a warm winter meal when it’s especially chilly outside. 

The washer, dryer, free WiFi, air conditioning, and gym amenities add comfort and convenience, making this stay unforgettable. 

And, the location just 1.1 miles from the Milwaukee Domes makes it the perfect place to stay while exploring unique places in Wisconsin in winter. 

It’s a must-visit destination for anyone who loves architecture and history at one of the best luxury cabins in Wisconsin. 

8. Ghost cabin in Waushara County –  Saxeville

river that flows next to the Ghost cabin in Waushara County in Saxeville, Wisconsin
Courtesy of VRBO

Winter retreats in Wisconsin are the perfect excuse to enjoy log cabins nestled among the captivating scenery of the state. 

I recently had the pleasure of visiting the iconic Stone Bridge Cabin, which did not disappoint. 

The classic log cabin is 10 feet from the famous Pine River in Waushara County. 

But, don’t let the rustic exterior fool you! The interior has been newly renovated and comfortably sleeps four people. 

As an avid fly-fishing enthusiast, I was excited to learn that this stretch of the Pine River is known for its prolific caddis and hexagenia hatches, with 18″ plus inch Brown trout commonly caught. 

Plus, dozens of other productive Central Sands trout streams are within a 30-minute drive. To top it off, a traditional “up-north tavern” is conveniently located across the river, offering a cozy and warm ambiance in winter. 

So, add Stone Bridge Cabin to your list of winter log cabin rentals in Wisconsin, and you won’t be disappointed!

9. Unique Cabin in the Woods – Pepin

living room with sofa in front of a fireplace at Unique Cabin in the Woods in Pepin, Wisconsin
Courtesy of VRBO

This spacious and unique cabin in Pepin boasts three cozy bedrooms, two pristine bathrooms, and all the necessary amenities, including a fully equipped kitchen, washer, dryer, and even air conditioning. 

The outdoor space is perfect for enjoying the serene surroundings. 

It includes a barbecue grill for family cookouts, the reason why it’s considered one of the best secluded cabins in Wisconsin.  

The upper loft provides a stunning view of Lake Pepin, and the large stone fireplace creates an inviting atmosphere for relaxation and gatherings. 

While the cabin provides plenty of peace, it is also within walking distance of many local attractions such as Villa Bellezza, Pepin Marina, and the Pickle Factory. 

A short drive will take you to Stockholm or even The Hidden Meadows, where you can enjoy the scenic views and activities all year round. 

As someone who loves exploring new places, I recommend considering this charming cabin if you’re wondering what to do in Wisconsin in winter.  

It’s the perfect getaway for family and friends, and I can guarantee it will quickly become a favorite vacation spot.

10. Riverdance Cabin – Amherst

living room seen from the first floor at the Riverdance Cabin in Amherst, Wisconsin
Courtesy of VRBO

If you’re looking for a one-of-a-kind place to stay in the heart of Wisconsin, the Riverdance Cabin in Amherst will sweep you off your feet.  

Every detail in this beautiful cabin was carefully considered, from the handcrafted countertops to the exquisite tree staircase. 

And with a hot tub and air conditioning, you will be comfortable no matter the weather. 

The cabin is pet-friendly so that you can bring your furry friend along for the adventure. 

Outside, you’ll find plenty of space to relax and enjoy the beautiful surroundings, including a barbecue grill and outdoor seating. 

And with biking, canoeing, trout fishing, hiking, cross-country skiing, and snowshoeing all nearby, you’ll have plenty of things to do in Winter in Wisconsin. 

This cabin was built sustainably, with repurposed materials and green insulation, so you can enjoy your stay knowing that you’re helping to protect the environment. 

Amherst Riverdance Cabin is the perfect choice for a unique and unforgettable vacation.

My final thoughts on the most unique places to stay in Wisconsin in Winter

exterior of one of the most unique places to stay in Wisconsin in winter

My exploration of unique places to stay in Wisconsin in Winter was enlightening and led me to conclude that winter can provide us with a wealth of wonderful experiences. 

As daunting and challenging as winter can be, there are many ways to embrace its unique draw and enjoy its magical beauty. 

With embracing the spirit of the season comes unique opportunities for travel experiences. 

In Wisconsin, you can access some incredible places for winter getaways — from local ski resorts, cabins in rugged landscapes, or deliciously cozy retreats. 

Don’t let another winter pass without taking advantage of these beautiful attractions — make time for yourself this year by checking out one of these fantastic places! 

FAQ about the most unique places to stay in Wisconsin in Winter

What are the most unique places to stay in Wisconsin in winter for couples?

Some of the most unique places to stay in Wisconsin in winter for couple are Rustic Ridge Log Cabins in Merrimac, the 1954 Rail Road Caboose Cabin with Relaxing Hot Tub in Aspen, or the Secret Cottage in Oxford.

What are the best romantic places to stay in Wisconsin?

Some of the best romantic places to stay in Wisconsin are the Pfister Hotel, Hilton Garden Inn Milwaukee Downtown, or Stout’s Island Lodge in Birchwood.

What are the most unique places to stay in Wisconsin Dells?

Some of the most unique places to stay in Wisconsin Dells are Natura Treescape Resort, Aloha Beach Resort & Suites, or Cedar Lodge and Settlement.