Downtown Chicago Cottage Rentals & Holiday Homes

Find the best cottages in Downtown Chicago - We found 2486 exact matches

About Downtown Chicago Cottage Rentals on Float Homes

Looking for charming lakeside or dock cottages near Downtown Chicago for your next getaway? Float Homes offers more than 2486 luxury lakeside and dock cottage and floating home rentals, perfect for your family or group trip. Discover cottages located just a few steps from the water, featuring amenities like hot tubs, kid-friendly accommodations, and easy access to top local attractions. These rentals ensure an exceptional experience on the water, with options that cater to large groups, families, friends, or couples.

Planning a lakeside retreat or a water-based getaway for your group? Float Homes provides a variety of floating home rentals including dock and lakeside cottages, houseboats, floating cabins, and more, connecting you directly with owners to secure the best prices.

Explore 2486 lakeside cottages and exceptional water-based accommodations in Downtown Chicago with Float Homes. Find unique Airbnb-style and VRBO-style cottages perfect for your weekend escape, spring break, or annual vacation, all within your budget.

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Frequently Asked Questions About Downtown Chicago Rental Cottages

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 Cottage Rentals in Downtown Chicago:

The average cost for a cottage rental in Downtown Chicago is $399 per night. FloatHomes.com has a wide list of great cottages near Downtown Chicago that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage rentals in Downtown Chicago that allow you to bring your pet:

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

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Downtown Chicago to find one that works for you.
As of 2025, the data from Float Homes shows that there are Over 2486 private swimming pools or cottages with indoor pools in the Downtown Chicago area along with other great amenities.
About 2486 cottages in Downtown Chicago boast of premium hot tubs. Some of the popular places to stay with hot tubs include:See all holiday vacation rentals in Downtown Chicago on Float Homes
Yes, there are luxury cottages in Downtown Chicago. Find more luxury, lakefront, winter, & last-minute cottage rentals near Downtown Chicago.