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Cozy Airbnbs Near Chicago for a Long Weekend Getaway

Last year due to the global pandemic, we spent much of our time exploring the Midwest and taking short road trips from Chicago. Since staying in Airbnbs was among the safest ways to travel, we ended up visiting quite a few of them. Our mission was to find the most charming rentals. Here is a list of our favorite cabins near Chicago for long weekend getaways and road trips.

the glass house on birch bluff in door county, wi


This charming Airbnb in Fish Creek, Wisconsin was named in honor of Fredrica “Fritzie” Glass, the artist, teacher, and writer who built this cottage in 1969. The cottage sits atop a private bluff, surrounded by trees. It’s a perfect place for a quiet escape from the hustle and bustle of city life. 

This stylish design-oriented vacation rental is a true gem. The moment we saw this listing on the Airbnb website, we had to book it right away! The cottage is beautiful and charming, and it’s thoughtfully designed. There were fresh flowers in every room, as well as plants, books, and lots of board games. A bottle of wine and chocolates were waiting for us upon arrival—small touches that always make us feel right at home.

The cottage has a beautiful wrap-around deck, perfect for barbecue dinners in the summer.  There is also a fire pit only 10 yards away from the house. We spent one afternoon sitting by the fire, sipping wine, and roasting marshmallows while snow fell around us. 

The house itself is very compact. It has two small bedrooms and will fit three guests comfortably. There is a small but very functional kitchen, a living room with a comfortable couch, an electric fireplace, and a TV.

Our favorite thing about The Glass House is that it is very secluded and at the same time, it’s close to state parks, hiking trails, and other areas of interest. It’s an amazing home base for exploring Door County.

fernside a-frame in indian river, mi


FERNSIDE A-FRAME IN INDIAN RIVER, MI

This gorgeous a-frame cabin, situated on the banks of the Sturgeon River in Indian River, Michigan, was everything we ever dreamed of! It’s picture-perfect both inside and out and combines rustic charm with modern decor elements—the best of both worlds!


There is one bedroom on the first floor and another loft bedroom on the second floor. The cabin sleeps up to 4 people, but no pets are allowed. The open floor concept makes the place feel very spacious. In the morning it’s filled with sunshine, and at night you can see the stars through the big windows. 

Upon arrival, we found a bag of fresh coffee and some pastries from a local coffee shop waiting for us on the countertop, as well as a bottle of wine and a beautiful cheese plate in the fridge. Delicious and considerate touches that made us feel very welcome!

The cabin sits on the edge of the river and is surrounded by wildlife. Expect to be greeted by ducks in the morning, and to see lots of fish, birds, and other animals. The backyard is secluded and is perfect for enjoying a picnic or a bonfire with s’mores. 

One of the amazing things about this part of Michigan is how dark the sky gets at night. On a clear night, you can see the stars from inside the cabin or out on the back deck. Such a magical getaway spot!

ski chalet in harbor springs, mi


Last November we spent almost an entire week in this charming cabin in Northern Michigan, and we only wish we could have stayed there longer (maybe even forever?). This newly remodeled a-frame is located in a quiet little neighborhood at the base of Nub’s Nob Ski Resort. 

The cabin itself is not huge, but it feels really spacious and airy inside because of the huge windows on both sides. There is a lot of natural light inside even on a gloomy day. There is only one loft bedroom with a queen-size bed, so this place will fit two people comfortably, and pets are allowed too!

The cabin truly feels like a home away from home with its fully equipped kitchen where we cooked all our meals (including a Thanksgiving dinner for two), a lovely dining area with a big wooden table, and a living room area with two couches and a fireplace. The fireplace wasn’t hooked up when we were staying there, but it should be working now. 

If you’re looking for a place to disconnect from the outside world, this place is it. There is no wifi or TV, which may be an issue for some guests, but not for us! We enjoyed spending a few days off the grid. There are so many board games, books, and cozy nooks for reading. And if you do get bored, there are plenty of fun things you can do in this part of Michigan! 

The owners have a pottery business, so this cabin is filled with gorgeous handmade ceramic products—from dishes and mugs in the kitchen, to vases, trinket plates, and soap holders in the bathrooms. 

camp wandawega


Only a two-hour drive from Chicago, Camp Wandawega has become one of our favorite weekend getaway spots. We have already visited twice, in the winter and the summer. No matter the season, this rustic campground is a great place to escape the city for a while.

Camp Wandawega offers various accommodation types, ranging from vintage cabins and camping clusters to a renovated 3-bedroom cottage. All of these options will provide you with a slightly different experience. Read a more detailed review of Camp Wandawega HERE.

We might be biased, but we think that winter might be one of the best times to visit Camp Wandawega. It’s quiet and peaceful. The frozen lake and surrounding areas will be your playground for the day, and at night you can relax by the fire and play board games at the lodge.

Camp Wandawega’s Treehouse is like a magical portal back into childhood. Up high in the branches, far from the cares of the world, you’ll feel like a kid again. Here you’ll find lots of books and interesting nooks for reading them. 

spring lake cabin in iron mountain, mi


We stayed at the Spring lake Cabin at the end of September, just when all the trees in the area started to change color. This is, hands down, the best time to be here! 

This single-room cabin is quite small, but surprisingly feels very spacious! There are two beds and a couch, so it can fit 2-4 people comfortably. We loved the rustic design and cozy atmosphere of this place. 

The Spring Lake Cabin is pet-friendly, and you can bring your dog for an extra fee. 

One of the best features of this property is the back deck that overlooks a spacious yard that slopes down to Spring Lake. The trees in the yard were already turning yellow and orange—such a beautiful sight! They have a nice little patio setup on the deck, and this is where we liked to drink our morning coffee.

All guests have access to their own fire pit, and a dock with two kayaks and a paddleboat. The lake is literally steps away from the cabin. It doesn’t have public access, so it’s very quiet here, especially during the off-season.

We enjoyed these peaceful moments by the lake surrounded by autumn foliage. It was such a lovely and relaxing escape. 

Kodiak on Long Lake


Kodiak on Long Lake Cabin in Wisconsin is a beautiful vacation rental situated on the shores of Long Lake in the heart of Wisconsin’s Northwoods. It’s one of the most beautiful cabins we’ve stayed in – definitely worth a 6-hour drive from Chicago!

The cabin is surrounded by towering pines and is just a short walk from the lake, making it the perfect spot for nature lovers. We arrived there during a big snowstorm and we couldn’t imagine a more perfect place to be snowed in. Even on the coldest days, the cabin stays warm and toasty!


The interior of the cabin is beautifully decorated with a style that combines both modern and rustic elements. We loved the modern Scandinavian design with high ceilings in the main living room/dining area, big windows, and an abundance of light.

Kodiak cabin faces west and overlooks the lake, so all guests have a front-row seat to the stunning colors of the sunset reflected on the water or snow. The natural surroundings of the cabin, with its towering pines and peaceful setting, would only add to the serenity of the experience.

Kodiak on Long Lake Cabin features all the amenities you need for a comfortable and enjoyable stay. There you’ll find two bedrooms, a fully equipped kitchen, and a dining and living area with a fireplace. You can come with you pup since the cabin is dog-friendly! It’s a wonderful place to relax and unwind.

Lake Cabin in Kohler, WI


The Lake Cabin at the American Club in Kohler, Wisconsin is a luxurious cabin near Chicago. It’s only a 2.5-hour drive away from the city! The cabin overlooks lake Michigan and is surrounded by lush forests and beautiful gardens. It’s a truly special place to escape to.

The decor of the cabin is very elegant yet cozy. Most of the time we spent curling up with a good book and watching movies by the fireplace in the living room.

The fully equipped kitchen has everything you might need. One of the best features of this cabin is the grocery delivery service that is offered by The American Club. By the time we arrived, the fridge was stocked with all the necessary ingredients for preparing gourmet meals as well as coffee, tea, and various snacks.

The cabin offers panoramic views of the serene Lake Michigan. We took advantage of this location and woke up in time to watch the sun rise above the lake. During the warmer months, the private deck is the perfect place to unwind after a day of exploring the surrounding area.


Guests of the Lake Cabin can also enjoy access to the amenities of the American Club resort, including fine dining restaurants, a spa, and a fitness center. Whether you’re looking for a romantic escape or a family vacation, the Lake Cabin at the American Club is the perfect destination. We truly enjoyed our stay at the Lake Cabin and can’t wait to come back!

Hayward Haus in Hayward, WI


Hayward Haus is one of my favorite cabins in Wisconsin. It sits on the shore of Upper Twin Lake in Hayward, Wisconsin, not far from Chequamegon-Nicolet National Forest. As it takes just over 6 hours to drive there from Chicago.

Hayward Haus was inspired by minimalist Scandinavian architecture that blends into the surrounding environment. The mono-pitched roof and natural interior elements such as wood paneling, plants, and floor-to-ceiling windows help the cabin achieve just that—they make you feel like you’re part of the outdoors.

This space is bright and airy, as the tall windows allow ample light to pour in even on overcast, dreary days. The furniture throughout is simple but beautiful, complementing the minimalist cabin structure. 

Outside is a wrap-around wooden deck that spans the back and side of the cabin. Here there are lounge chairs, a grilling area, a table for dining, and a stone fire pit.

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