165+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Chester Highlands pickleball Stays, Resort Rentals, & Homes

About Chester Highlands Vacation Rentals

Discover over 165 amazing vacation rental options in Chester Highlands 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 Chester Highlands.

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 693.08 ft², with prices averaging US $292 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 Chester Highlands.

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Top Pickleball-Ready Accommodation Types in Chester Highlands

Type Count
Vacation Homes 78
Holiday Apartments 70
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Chester Highlands

★ 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 Chester Highlands with PickleTrip™.

Weather in Chester Highlands, IL

View the weather forecast for Chester Highlands before booking your Chester Highlands 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 Chester Highlands, IL

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


Navy Pier
Wrigley Field
McCormick Place
Millennium Park
Union Station
Soldier Field
Willis Tower
Art Institute of Chicago
United Center
Grant Park
John G. Shedd Aquarium
Chicago Museum of Science and Industry
Chicago Theatre
Chicago Riverwalk
Field Museum of Natural History
University of Chicago
Brookfield Zoo
John Hancock Center
Lincoln Park Zoo
Water Tower Place

Other Places to Stay in Chester Highlands, IL


Gresham 149 Properties
Auburn Gresham 140 Properties

Frequently Asked Questions About Chester Highlands?

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

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

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

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 165 properties listed in Chester Highlands 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.

Nearby Neighborhood (1) 
Neighborhood Property Count
Chatham Vacation Rentals in Chicago, Illinois 273

People Also Ask

There are 165 Chester Highlands, IL Vacation Rentals

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