Downtown Chicago Winter Rentals & Holiday Homes

Discover winter rentals Downtown Chicago - We found 371 exact matches

About Downtown Chicago Winter Rental on Float Homes

Float Homes offers a diverse array of floating homes and water-based accommodations in Downtown Chicago, IL, perfect for your winter retreat or seasonal escape. Our listings include luxurious houseboats, overwater villas, floating cabins, and other unique water accommodations, ensuring travelers find their ideal stay. Our floating accommodations boast premier amenities such as Wi-Fi, heated outdoor swimming pools, hot tubs, private decks, and panoramic water views, perfect for an unforgettable getaway.

Whether you're looking to relax by the water in a serene setting or enjoy thrilling water adventures, Float Homes connects you to the finest floating homes, houseboats, and other luxury rentals. From tropical climates or scenic, snow-capped regions, our collection ensures your winter escape on the water is nothing short of amazing.

Float Homes offers great deals for travelers seeking rentals in Downtown Chicago. Choose from thousands of winter vacation rentals hassle-free. Use our interactive map to discover all floating home options in and around Downtown Chicago.

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Frequently Asked Questions About Downtown Chicago Winter Rentals

There are a lot of options in Downtown Chicago. If you plan on staying in the Downtown Chicago area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Downtown Chicago:

The average cost for winter rentals in Downtown Chicago is $546 per night. FloatHomes.com has a wide list of great winter places to stay near Downtown Chicago that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage/chalet rentals in Downtown Chicago that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Downtown Chicago on Float Homes

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Downtown Chicago to find what works for you.
As of 2025, the data from Float Homes shows that there are over 371 private swimming pools or indoor pools accommodations near Downtown Chicago along with other great amenities.

About 371 holiday rentals in Downtown Chicago boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:

Yes, there are many luxury places to stay in Downtown Chicago for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Downtown Chicago with all the best amenities for your next trip.