133+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Waukegan pickleball Stays, Resort Rentals, & Homes

About Waukegan Vacation Rentals

Discover over 133 amazing vacation rental options in Waukegan 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 Waukegan.

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 529.86 ft², with prices averaging US $237 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 Waukegan.

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Top Pickleball-Ready Accommodation Types in Waukegan

Type Count
Vacation Homes 70
Holiday Apartments 27
Villas 1

Use these Quick Filters to Find a Vacation Rental in Waukegan

★ 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 Waukegan with PickleTrip™.

Weather in Waukegan, IL

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

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Waukegan, IL

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


Genesee Theater
Waukegan Harbor
Waukegan SportsPark
Bonnie Brook Golf Course
Jack Benny Center for the Arts
Three Brothers Theatre
The People's Choice Family Fun Center
Waukegan BMX Track
Urban Edge Gallery
Visual Arts Center
North Beach
Vista Medical Center - East
Naval Base Great Lakes
Six Flags Great America
Gurnee Mills
Wilmot Mountain
Illinois Beach State Park
Volo Auto Museum
Pleasant Prairie RecPlex
Pleasant Prairie Premium Outlets

Other Places to Stay in Waukegan, IL


Waukegan SportsPark 210 Properties
Park City 137 Properties
The People's Choice Family Fun Center 132 Properties
Visual Arts Center 73 Properties
Urban Edge Gallery 67 Properties
Genesee Theater 67 Properties
Three Brothers Theatre 67 Properties
Waukegan Harbor 65 Properties
Vista Medical Center - East 62 Properties
North Beach 54 Properties
Bonnie Brook Golf Course 52 Properties
Jack Benny Center for the Arts 47 Properties

Frequently Asked Questions About Waukegan?

What are the top vacation rentals, resorts, and hotels in Waukegan 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 Waukegan. 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 Waukegan!

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

Looking for a fun and active getaway with pickleball courts in Waukegan? 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 Waukegan?

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 133 properties listed in Waukegan in 2025, 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.


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There are 133 Waukegan, IL Vacation Rentals

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