18479+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Illinois

Illinois pickleball Stays, Resort Rentals, & Homes

About Illinois Vacation Rentals

Discover over 18479 amazing vacation rental options in Illinois with pickleball courts or nearby facilities. From resorts to hotels, villas to condos, PickleTrip connects you with a vast selection of pickleball-ready amenities at great prices, providing you with the perfect spot to base your next pickleball vacation. Stay and Play pickleball When You Travel and uncover great stays in Illinois.

Find exclusive last-minute deals on vacation rentals, resorts, and hotels with private courts and nearby facilities with PickleTrip™, whether you're traveling solo or with a group. Our platform offers a variety of stay options, from vacation rentals to Airbnb-style properties, all with private pickleball courts or nearby facilities. Compare options from multiple suppliers with a single click to find the perfect stay that fits your budget and style. Places to stay near pickleball courts are an average of 752.28 ft², with prices averaging US $305 per night.

With PickleTrip™, you can easily search for and book your next pickleball vacation rental with courts or nearby facilities. Our platform connects you with the ideal holiday rental to create a lifetime of travel memories. Prices listed are often discounted versus rack rates, so you can secure your perfect place to stay today and get ready to play pickleball in Illinois.

Show more
Show less

Top Pickleball-Ready Accommodation Types in Illinois

Type Count
Holiday Apartments 6531
Vacation Homes 6519
Cottages 197
Villas 79

Use these Quick Filters to Find a Vacation Rental in Illinois

★ Pro Tip: PickleTrip™ is a travel platform, connecting avid pickleball players and enthusiasts with a variety of vacation rentals, resorts, and hotels featuring private pickleball courts or nearby facilities. We curate a vast selection of properties from trusted sources, providing you with unbeatable options and pricing to find the perfect pickleball getaway. Experience unforgettable pickleball matches in Illinois with PickleTrip™.

Weather in Illinois, US

View the weather forecast for Illinois before booking your Illinois Vacation Rentals to confirm your best time to go.

December - February
High 52°F       Low 19°F
March - May
High 73°F       Low 33°F
June - August
High 86°F       Low 57°F
September - November
High 81°F       Low 31°F

Top Attractions Around Illinois, US

PickleTrip offers a large selection of top attractions around Illinois . Research things to do on your vacation before you visit Illinois.


Navy Pier
Wrigley Field
McCormick Place
Millennium Park
Union Station
Soldier Field
Willis Tower
Art Institute of Chicago
Naval Base Great Lakes
United Center
Grant Park
University of Illinois at Urbana-Champaign
John G. Shedd Aquarium
Chicago Museum of Science and Industry
Chicago Theatre
Peoria Civic Center
Chicago Riverwalk
Field Museum of Natural History
Six Flags Great America
University of Chicago
Brookfield Zoo
Northwestern University
John Hancock Center
Allstate Arena
Lincoln Park Zoo
Starved Rock State Park
Water Tower Place
Loyola University Chicago
Schaumburg Convention Center
Rosemont Theatre

Other Places to Stay in Illinois, US


Chicago 6,938 Properties
Cook County 5,408 Properties
Chicago 4,189 Properties
Central Chicago 1,686 Properties
Downtown Chicago 1,548 Properties
West Side 806 Properties
The Loop 717 Properties
North Side 654 Properties
Jo Daviess County 646 Properties
Near North Side 617 Properties
Lake County 574 Properties
Galena 571 Properties

Frequently Asked Questions About Illinois?

What are the top vacation rentals, resorts, and hotels in Illinois with Courts?

Experience the ultimate pickleball vacation with PickleTrip™. We offer a variety of premium rental properties, resorts, and hotels with private pickleball courts or nearby facilities in Illinois. Whether you're a beginner or a seasoned player, we have the perfect destination for you to stay and play. Book now and discover the best pickleball vacation spots in Illinois!

How many pickleball-ready properties have private pools in Illinois?

Discover 739 accommodations with private or nearby pickleball courts in Illinois. Some of the best destinations to stay and play pickleball are:

Which vacation rentals, resorts, or hotels in Illinois is best for families looking for a pickleball-getaway?

Looking for a fun and active getaway with pickleball courts in Illinois? With PickleTrip™, you'll have access to a wide selection of top-rated properties that offer private pickleball courts or nearby facilities. Make the most of you getaway and ace your A-game while you travel.

How many PickleTrip vacation rentals or resorts are available in Illinois?

PickleTrip™ offers a diverse selection of properties with private pickleball courts or nearby facilities to enhance your pickleball experience on your next trip. With a combination of established great stays and new options in top locations, PickleTrip™ has over 18479 properties listed in Illinois in 2026, and the number only continues to grow. By consolidating listings from various providers, PickleTrip™ brings you the best luxury stays for a sporty, professional, and fun travel experience.


People Also Ask

There are 18479 Illinois, US Vacation Rentals

Recently Booked Vacation Rentals in Illinois