Worldwide icon-chevron-right North America icon-chevron-right United States icon-chevron-right Illinois icon-chevron-right Chicago icon-chevron-right The coziest Airbnbs you can rent near Chicago this winter

Heads up! We’re working hard to be accurate – but these are unusual times, so please always check before heading out.

cozy airbnb
Photograph: Courtesy Airbnb

The coziest Airbnbs you can rent near Chicago this winter

Whether you're looking to stay in Chicago or go for a weekend trip, these Airbnbs offer an ultra-cozy wintertime escape.

By Emma Krupp
Advertising

Love it or hate it, winter is the coziest time of year in the Midwest—you might as well lean into the season with a stay at a warm, inviting vacation rental. Take a day trip from Chicago and check out Airbnb cabins just over the border in Wisconsin and Michigan, or stick closer to home for a cozy Chicago staycation; both options provide ample possibilities for intimate evenings away from the elements. Banish your fears of freezing temps and transform them into daydreams about toasty hearths at these cozy Airbnbs near Chicago.

Note: please check the latest travel guidance before booking your trip

This article includes affiliate links. These links have no influence on our editorial content. For more information, click here.

RECOMMENDED: The most secluded getaways from Chicago

The coziest Airbnbs near Chicago

Southwest Michigan cozy Airbnb
Southwest Michigan cozy Airbnb
Photograph: Courtesy Airbnb

Modern farmhouse cottage in southwest Michigan

Looking to unplug among nature for a couple of days? Ditch the city and drive just under an hour and a half from downtown Chicago to reach this sweet farmhouse cottage in Sawyer, Michigan. The 14-acre premises feature pastures dotted with farm animals, woods and a barn. Inside the cottage, an elegant, modern kitchen—equipped with warm wooden butcher block counters and a bounty of cooking tools—offers opportunity for whipping up a hot meal after a long day of hiking and exploring.

Batavia cozy Airbnb
Batavia cozy Airbnb
Photograph: Courtesy Airbnb

Log cabin in the woods

Few styles of homes scream "cozy" more than a log cabin—and this rental, located in suburban Batavia along the Fox River, is no exception. Settle in among the surrounding oak forest and relax in front of a wood-burning stove, or bundle up and gaze at the scenery from a covered deck (doing so with a warm beverage in hand makes the views that much better). The home has three bedrooms, but we're especially fond of the loft option, which features a sky window perfect for soaking up the morning light.

Advertising
cozy airbnb
cozy airbnb
Photograph: Courtesy Airbnb

Bright and homey Albany Park apartment

You don't need to leave Chicago for a cozy getaway! Just book a weekend at this plant-filled Albany Park apartment, which manages to be airy and intimate all at once. Grab takeout and a growler from one of the many excellent restaurants and breweries nearby and settle in for an evening on a plush couch in front of the fireplace. Once you've finished eating, you'll find plenty of entertainment in the form of games and coloring books.

christmas tree farm cozy Airbnb
christmas tree farm cozy Airbnb
Photograph: Courtesy Airbnb

Glamping cabin on Cold Spring Tree Farm

For a more rustic experience, head just over the border to this single-room cabin in Whitewater, Wisconsin, which is nestled on the premises of a 40-acre Christmas tree farm. You'll have to be comfortable with giving up certain conveniences (there's no running water or toilets, though fresh water in thermoses, an outhouse and indoor bucket toilet are provided), but it's tough to beat the cabin's stone-walled charms: Just imagine curling up in front of the toasty wood-burning stove after a long day of ice fishing. 

Advertising
cozy airbnb
cozy airbnb
Photograph: Courtesy Airbnb

Floyd's Cottage

This southwest Michigan rental is the home of your cottagecore dreams, complete with eclectic decor, wood floors and a jacuzzi in the master bathroom. Sit down with a good book in a rocking chair on the wraparound porch, and don't forget to make the most of the cottage's proximity to Lake Michigan by taking a walk on the beach—some say the lake is even more beautiful in the winter!

cozy airbnb
cozy airbnb
Photograph: Courtesy Airbnb

The Northwoods on the North Side of Chicago

Who would have ever thought a garden unit could look so much like a Wisconsin lodge? This Rogers Park rental somehow manages to pull the effect off, utilizing soft carpet, fish-themed decor and wood-paneled walls to transport guests to the boreal environs of the Northwoods (minus the six-hour drive). Crack open a can of Schlitz in front of the fireplace and it'll be just like the real deal.

Advertising
cozy airbnb
cozy airbnb
Photograph: Courtesy Airbnb

Historic Racine retreat home

Steal away from Chicago to this 1858 historic abode in Racine, Wisconsin—located just five blocks away from the shores of Lake Michigan—that's full of homey character. A couple of deep leather couches and some board games will make for lovely evenings spent by the hearth, while a two-story sunroom allows you to make the most out of winter light. Remember to read up on the history of the home before you leave!

cozy airbnb
cozy airbnb
Photograph: Courtesy Airbnb

Bright Madison Street loft

Hop on the Blue Line for a cozy escape to this luxe Forest Park loft located on the top floor of a renovated Masonic Temple. The apartment's exposed brick, leather and burnished decor make for an almost speakeasy-type feel—but you'll also have access to a balcony if you'd like to take a break from the fireplace for crisp winter air and incredible views.

Advertising
cozy airbnb
cozy airbnb
Photograph: Courtesy Airbnb

Country cabin, birder's paradise

This farmhouse cabin just south of Madison is small and snug, making it a perfect getaway for a couple (and even a pet, as long as you ask ahead of time). Go cross-country skiing on the sprawling premises and bring your binoculars to keep an eye out for birds—up to 46 species have been known to make an appearance on a good day. In the evening, soothe your tired muscles with a relaxing rest in the cabin's outdoor sauna. 

cozy airbnb
cozy airbnb
Photograph: Courtesy Airbnb

The Bay Chalet

Enjoy the bustle of Lake Geneva at this peaceful cabin—billed as a "chalet" thanks to its ski resort vibes—tucked into the woods (even though it's only a two-minute drive to Williams Bay beach and other attractions). Cuddle up indoors under a furry blanket or endeavor to build a roaring fire in the pit in the backyard; either way, you're in for a restful weekend. 

More places to escape to this winter

Recommended

    More from Airbnb

      You may also like

        Advertising