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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 PickleTrip

Searching for cottages to rent near Chicago? PickleTrip™ features more than 46 cottages that are perfect for your next pickleball getaway. Plan your ultimate holiday and discover luxury cottage rentals that are a few miles away from the lake or beach and have access to private courts or nearby facilities. 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. PickleTrip™’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? PickleTrip™’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.

PickleTrip™ boasts of 46 holiday cottages and places to stay in Chicago. The site provides unique Airbnb, VRBO, pickleball-ready 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.

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Frequently Asked Questions About Chicago Rental Cottages

The average cost for a cottage rental in Chicago is $367 per night. PickleTrip 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 PickleTrip

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 PickleTrip 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 PickleTrip
Yes, there are luxury cottages in Chicago. Find more luxury, lakefront, winter, & last-minute cottage rentals near Chicago.