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Chicago Cottage Rentals & Holiday Homes

Find the best cottages in Chicago - We found 46 exact matches

About Chicago Cottage Rentals on BedroomVillas

Seeking incredible premium cottages to rent near Chicago? BedroomVillas features more than 46 cottages that are ideal for your next trip. Discover high-end 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 attractions, to give guests the best travel experience they could ever wish for. BedroomVillas’ cottage listings come in all shapes and sizes for large groups, friends, or couples in Chicago.

Are you planning to travel to a lakeside, beach, or mountain area? Then we've got the places for you. BedroomVilla’s cottage rentals and boutique resorts and rentals offer a great selection, giving you direct access to the owners of these cottage properties, and providing you the best opportunity to find a great price for a great stay.

BedroomVillas offers 46 luxury holiday cottages and places to stay in Chicago. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting within your budget. Relax with BedroomVillas.

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Frequently Asked Questions About Chicago Rental Cottages

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:

The average cost for a cottage rental in Chicago is $361 per night. BedroomVillas 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.
Yes, here are the top cottage rentals in Chicago that allow you to bring your pet:

See all pet-friendly vacation rentals in Chicago on BedroomVillas

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.
As of 2025, the data from BedroomVillas shows that there are Over 46 private swimming pools or cottages with indoor pools in the Chicago area along with other great amenities.
About 46 cottages in Chicago boast of premium hot tubs. Some of the popular places to stay with hot tubs include:See all holiday vacation rentals in Chicago on BedroomVillas
Yes, there are luxury cottages in Chicago. Find more luxury, lakefront, winter, & last-minute cottage rentals near Chicago.