1. USA
  2. Illinois
  3. Chicago
  4. Cottage Rentals

Cottages in Chicago

Stay in a Cottages in Chicago – Plan Your Next Vacation to Chicago Today!

About Chicago Luxury Rental on Smartours

Searching for cottages to rent near Chicago? Smartours features more than 52 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 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. Smartours’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Chicago.

Are you planning to travel to the lakeside, beach, or mountain area? Smartours’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.

Smartours boasts of 52 holiday cottages and places to stay in Chicago. The site provides unique Airbnb, VRBO, Smartours-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.

Frequently Asked Questions About Chicago Cottage Rentals

What are the top rated Cottage Rentals in Chicago?

There are a lot of options in Chicago. If you plan on staying in the 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 Chicago:

How much does it cost to rent a cottage in Chicago?

The average cost for a cottage rental in Chicago is $361 per night. Smartours has a wide list of great cottages near Chicago that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Do you have any rental cottages in Chicago that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Chicago to find one that works for you.

Are there quality cottages in Chicago that have indoor swimming pools?

As of 2026, the data from Smartours shows that there are Over 52 private swimming pools or cottages with indoor pools in the Chicago area along with other great amenities.