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4 Excellent Rental Getaways in Driving Distance from Chicago

The end of winter is getting closer by the day, which has many Chicagoans excited to fully enjoy the outdoors again soon–one of few certainties we do have in 2021. But even before then, now could be an excellent time to recharge the batteries with a quick weekend getaway. While vacation home rentals within a few hours in Chicago were busy last summer and should be busy again this year, it’s the offseason where the best deals can be had. And the Upper Midwest has no shortage of homes you’ll want to curl up within and not come back, warm weather or not.


Mix modern and remote at Northwest Indiana’s “Dune Farm House”

Looking for the modern comforts of an ornately furnished and designed home, while still being in a remote oasis? That will be a common theme throughout this list, but Michigan City’s Dune Farm House isn’t one to overlook. These comforts are combined with direct access to over five miles of trails through vast acreage of woods and prairies. The family-friendly operation features plenty of games inside and two bedrooms, along with a studio with an added daybed. The setting may be remote, but the overall location isn’t, as this home is just over an hour away from Chicago in Michigan City (which, no, is not in Michigan).


Amenities-packed A-frame delight in the northwest suburbs

This glorious architectural style would be worth a cozy weekend visit regardless, but what really sets this one apart are the entertainment options. The 20 acre property includes access to some amenities shared with the owner, including a swimming pool, hot tub, tennis court, sauna, sand beach, bonfire area, kayaks and other watercraft to utilize on the private lake. The pool and hot tub may not be available until summer, but this could be an ideal place to celebrate the non-freezing outdoors again come springtime. Despite its remote appearance, this home too is only around 50 miles from Chicago near Volo.


Door County “Peace of Beach” waterfront cottage

Is this a view you could get used to? Few homes can provide this level of intimacy with the open water, just 10 yards away. The home has two bedrooms and a hide-away sofa that can sleep two more, plus a fully equipped kitchen. The owner specifically markets the home as a “four season” getaway and the reviews back this up–if it’s too cold to enjoy the beach, it’s definitely prime time for the nice fireplace. The home is in Sturgeon Bay, Wisconsin, about a four hour drive from Chicago.


Scandanavian modern home near Traverse City

If you ever wanted a treehouse when you were younger but never got around to building one, this might be the next best thing. Alternatively, if you’ve ever wanted to live within an IKEA (without all of the other customers), this might be the next best thing for that as well. At around five hours from Chicago, this one is better suited if you enjoy road trips and perhaps want to make some stops along the beautiful Western Michigan shoreline along the way. But the home itself is an absolute treat, sleeping up to six people in three bedrooms. The euro-style kitchen and tasteful furnishings throughout (hello, bright yellow couch) look straight out of a magazine. Return from the lake beach to the comfy fire pit, where reviewers report excellent star gazing. Be sure to check the listing’s photos to get the full vibe.