84+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Flossmoor pickleball Stays, Resort Rentals, & Homes

About Flossmoor Vacation Rentals

Discover over 84 amazing vacation rental options in Flossmoor 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 Flossmoor.

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 830.21 ft², with prices averaging US $337 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 Flossmoor.

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Top Pickleball-Ready Accommodation Types in Flossmoor

Type Count
Vacation Homes 72
Holiday Apartments 4
Villas 1

Use these Quick Filters to Find a Vacation Rental in Flossmoor

★ 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 Flossmoor with PickleTrip™.

Weather in Flossmoor, IL

View the weather forecast for Flossmoor before booking your Flossmoor 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 Flossmoor, IL

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


Coyote Run Golf Course
Chicago Museum of Science and Industry
University of Chicago
Hollywood Casino Amphitheatre
Tinley Park Convention Center
State Street
Ameristar Casino East Chicago
Indiana Dunes National Park
Horseshoe Hammond Casino
SeatGeek Stadium
Jackson Park
University of Chicago Medicine
Majestic Star Casino
Midway Plaisance
Robie House
Orland Park Sportsplex
Lakefront Trail
River Oaks Center
Harrah's East Chicago Casino
Smart Museum of Art

Other Places to Stay in Flossmoor, IL


Coyote Run Golf Course 70 Properties

Frequently Asked Questions About Flossmoor?

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

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

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

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 84 properties listed in Flossmoor 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 84 Flossmoor, IL Vacation Rentals

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