Downtown Chicago Cottage Rentals & Holiday Homes

Find the best cottages in Downtown Chicago - We found 2393 exact matches

About Downtown Chicago Cottage Rentals on Rent By Owner

Searching for cottages to rent near Downtown Chicago? Rent By Owner features more than 2393 cottages that are perfect for your next trip. Discover luxury cottage rentals that are a few miles away from the lake or beach. These cottage rentals in Downtown Chicago have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. RBO’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Downtown Chicago.

Are you planning to travel to the lakeside, beach, or mountain area? RBO’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.

Rent By Owner boasts of 2393 holiday cottages and places to stay in Downtown Chicago. The site provides unique Airbnb, VRBO, RBO-style cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting within your budget.

Show more
Show less

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 $450 per night. RBO 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 Rent By Owner

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 Rent By Owner shows that there are Over 2393 private swimming pools or cottages with indoor pools in the Downtown Chicago area along with other great amenities.