5 cozy cottages perfect for an escape from Chicago

Frank Lloyd Wright cottage, secluded treehouse, and log cabin with character

By Ryan Smith and Sara Freund Updated Jan 27, 2020, 4:36pm CST

A cabin with a chimney, overgrown vines, and warm light coming from inside. — Grandpa’s Cabin

Let’s face it: Chicago can get bit a bleak during the winter months. From the slushy streets, salty sidewalks, and skyscraper-aided wind tunnels that blast you with cold air, to the chilly social vibes that come with the infamous tradition of parking “dibs”—sometimes you need an escape.

Thankfully, there are plenty of charming cabins tucked away in the woods or quiet rural areas a short distance away that are perfect for quick hibernations or weekend getaways. Here’s a roundup of several cabins or hideaways for rent in Wisconsin, Michigan, Indiana and elsewhere in Illinois that are within a four-hour drive of the city.

Seth Peterson Cottage in Mirror Lake State Park in Lake Delton, Wisconsin

A small brick and wood home in the middle of a wooded area.

A sloped roof living room with a built-in bench around the perimeter. There is a fireplace with two chairs in front of it.

There’s a long tale behind this secluded cottage at the edge of Mirror Lake near the Wisconsin Dells. But the short of it is—yes—you can actually rent a Frank Lloyd Wright-designed home for the weekend. The 900-square-foot might be the iconic architect’s smallest residential design, but it’s no less impressive (“It contained more architecture per square foot than any building Wright ever built,” said Wright’s assistant William Wesley Peters). Sleeps up to four for $300 a night.

Outpost Treehouse near East Leroy, Michigan

A cabin with a raised porch on the upper level. there are tall trees and a corn field surrounding the property.

A wooded cabin with a small kitchen area, a blue door, and table with coffee, fruit and muffins.

Inspired by fire lookout towers and hunting blinds, this quirky cabin is truly away from it all. It sits in the midst of a white pine forest in a 65-acre farm southwest of Kalamazoo. You can warm-up from the winter weather by building a campfire in the fire pit or take a hot shower in the first-level “bathhouse.” Climb the wooden path to the top to get a breathtaking view of nature from inside the second floor or from the wraparound deck—where wild turkeys, owls, and coyotes have been spotted. Sleeps up to two for $120 a night.

Four-acre estate near Ingleside, Illinois

An enclosed patio with a table, large deck, and beautiful views of a private lakefront.

A view outside the property shows a serene lake with a snow covered yard.

Here’s a perfect retreat for a large group. The 2,600-square foot home is just an hour long drive from Chicago. Get toasty near the fireplace and admire the views overlooking private stretch of Brandenburg Lake. If you want to squeeze in some winter activities, Wilmot Mountain is just 20-minute drive away and has skiing, snowboarding, and tubing. Sleeps up to 10 for $419 per night.

Grandpa’s Cabin near Savanna, Illinois

A rough stone fireplace with a wood mantel. There are two wooden rocking chairs and a window with sheer drapes.

It’s called Grandpa’s Cabin, but this snug log cabin in the rolling hills of western Illinois just minutes from the Mississippi River feels more like great-grandpa. Originally built in 1837, it was recently restored and filled with early 20th century antiques and oddities. It sleeps four for $150 a night.

Hilltop home near Fontana-on-Geneva Lake, Wisconsin

A home with asymmetrical gables, a grassy front yard, and a grey-black exterior.

An open kitchen and dining area surrounded by paned windows with views of trees.

Lake Geneva is Chicago’s getaway in the summer but fun can be had in the winter as well. Nestled behind a sanctuary of trees is this five-bedroom home on a hilltop. The original house was built in 1926, with an addition designed and built in 2000. It’s walking distance from a 21-mile path around the lakefront, restaurants, coffee shops, and the Abbey Resort which has an award-winning spa. Sleeps up to 10 for $464 per night.