Chicagoland Speedway Cottage Rentals & Holiday Homes

Find the best cottages in Chicagoland Speedway - We found 52 exact matches

About Chicagoland Speedway Cottage Rentals on PickleTrip

Searching for cottages to rent near Chicagoland Speedway? PickleTrip™ features more than 52 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 Chicagoland Speedway 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 Chicagoland Speedway.

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 52 holiday cottages and places to stay in Chicagoland Speedway. 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.

Show more
Show less

Frequently Asked Questions About Chicagoland Speedway Rental Cottages

Yes, here are the top cottage rentals in Chicagoland Speedway that allow you to bring your pet:

See all pet-friendly vacation rentals in Chicagoland Speedway on PickleTrip

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Chicagoland Speedway to find one that works for you.
As of 2025, the data from PickleTrip shows that there are Over 52 private swimming pools or cottages with indoor pools in the Chicagoland Speedway area along with other great amenities.
About 52 cottages in Chicagoland Speedway boast of premium hot tubs. Some of the popular places to stay with hot tubs include:See all holiday vacation rentals in Chicagoland Speedway on PickleTrip
Yes, there are luxury cottages in Chicagoland Speedway. Find more luxury, lakefront, winter, & last-minute cottage rentals near Chicagoland Speedway.