Winter Vacation Rentals near Chicago

From cozy tree houses to charming river cottages, Chicago weekend getaways ready to book here

Chicago is one of the largest cities in the US, and sits on the banks of the wonderful Lake Michigan. Despite being such a large city, the area surrounding Chicago is also one of distinct beauty that will make for a great winter getaway. Rolling farmland, lush forests, gentle hills, and acres of wetlands characterise this region. Sights such as Lake Michigan, Starved Rock State Park, Buckingham Fountain, Ohio River, the Shawnee National Forest, and the Chicago Lakefront Trail will be rendered a winter wonderland when covered in powdery snow and icy frost. The winter vacation rentals near Chicago will make choosing somewhere to stay a delight. Choose from deluxe log cabins with stunning interiors, luxurious lakeside retreats or charming river cottages, Chicago weekend getaways offer something of everything!


There are no more accommodations that exactly fit your criteria. You can try broadening your search by changing some of the filters or move and zoom-out into the map to show more results.

Accommodations without filters:

Oops! There are no results for your search.

Please try again with another location or different dates.