The Coziest Airbnb’s Within Road-Tripping Distance of Chicago

The Coziest Airbnb’s Within Road-Tripping Distance of Chicago

Average Reviews


Looks outside at snow slowly melting into grey slush. Looks at accumulation of takeout containers. Refreshes Netflix.

Yeah, it might be time to get out of the house…

… and into an even better house. Specifically, one of these six cozy Airbnbs that mean a beer in front of the fireplace or a dip in the hot tub are just a short drive away. Yes, they all have fireplaces and/or fire pits. Yes, they all have hot tubs.

And, yes, they’re all right this way…

Welcome to Galena, the quaintest little town this side of the Iowa border. Once you get here, you’ll be staying in a wood-paneled masterpiece surrounded by dense forest, none of which you’ll notice as you bounce back-and-forth between the fire and foosball tables. Galena, IL, $950, book here

This five-bedroom, five-bathroom manse is located in Oconomowoc, Wisconsin. Or, as you like to call it, “Your Private Peninsula,” where you are the king and court is held in front of a stone fireplace. Or maybe in the hot tub overlooking the lake. Remember, you’re the king. Oconomowoc, Wisconsin, $455, book here

Maybe it was the buffalo head over the fireplace that drew you to this quirky Wisconsin ranch. Or the vintage slot machines. Or the wooden bar illuminated by stained glass fixtures and decorated with fishing memorabilia. Either way, you’re here, and there’s more than a lot to take in. Markesan, Wisconsin, $300, book here

It might not look like much at first, but step inside and, bam: Mid-Century Modern wonderland. Is there a sunken living room with a slab fireplace? Absolutely. A rose-tinted bathroom with a gold-accented bathtub? Of course. Teepee out back? Why not. Clearly, that “bam” was called for. Lakeside, Michigan, $500, book here

Picture this: You’re sitting on the veranda overlooking Lake Michigan and sipping on beers that you picked up from nearby Greenbush. The urge to hop in the hot tub strikes, so you hot tub. Then you fire pit. Then you repeat as necessary. Three Oaks, Michigan, $545, book here

Did we save the best for last? That depends on if you think a log cabin castle with a movie theater and fireplace-adjacent leather furniture is the “best.” Did we mentioned the lakeside fire pit and barrel-shaped sauna? Yes. Yes we did. Eagle River, Wisconsin, $1,100, book here


0 Rating
0 Favorite

Claim Business

Is this your business?

Claim listing is the best way to manage and protect your business.