97+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  4. Des Plaines

Des Plaines pickleball Stays, Resort Rentals, & Homes

About Des Plaines Vacation Rentals

Discover over 97 amazing vacation rental options in Des Plaines 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 Des Plaines.

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 950.02 ft², with prices averaging US $332 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 Des Plaines.

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Top Pickleball-Ready Accommodation Types in Des Plaines

Type Count
Vacation Homes 59
Holiday Apartments 15
Villas 4

Use these Quick Filters to Find a Vacation Rental in Des Plaines

★ 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 Des Plaines with PickleTrip™.

Weather in Des Plaines, IL

View the weather forecast for Des Plaines before booking your Des Plaines 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 Des Plaines, IL

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


Rivers Casino
McDonald's Museum
Apache Park
Lake Park
Arndt Park
AMITA Health Holy Family Medical Center Des Plaines
Holy Family Hospital
Holy Family
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
John G. Shedd Aquarium

Other Places to Stay in Des Plaines, IL


Rivers Casino 234 Properties
Arndt Park 233 Properties
Apache Park 227 Properties
Lake Park 221 Properties
Oakton 195 Properties
Norma 160 Properties
McDonald's Museum 128 Properties
AMITA Health Holy Family Medical Center Des Plaines 105 Properties
Holy Family Hospital 105 Properties
Holy Family 105 Properties

Frequently Asked Questions About Des Plaines?

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

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

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

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 97 properties listed in Des Plaines 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.

Nearby Neighborhood (1) 
Neighborhood Property Count
O'Hare Vacation Rentals in Chicago, Illinois 65

People Also Ask

There are 97 Des Plaines, IL Vacation Rentals

Recently Booked Vacation Rentals in Des Plaines