71+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Skokie pickleball Stays, Resort Rentals, & Homes

About Skokie Vacation Rentals

Discover over 71 amazing vacation rental options in Skokie 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 Skokie.

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 535.3 ft², with prices averaging US $295 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 Skokie.

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Top Pickleball-Ready Accommodation Types in Skokie

Type Count
Vacation Homes 27
Holiday Apartments 23

Use these Quick Filters to Find a Vacation Rental in Skokie

★ 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 Skokie with PickleTrip™.

Weather in Skokie, IL

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

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


Skokie Theatre
North Shore Center for the Performing Arts
Illinois Holocaust Museum and Education Center
Adagio Teas
Emily Oaks Nature Center
Illinois Science and Technology Park
Schaefer's Wines and Liquors
Northshore University Health System Skokie Hospital
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 Skokie, IL


Schaefer's Wines and Liquors 227 Properties
Emily Oaks Nature Center 224 Properties
Northshore University Health System Skokie Hospital 219 Properties
North Shore Center for the Performing Arts 205 Properties
Illinois Science and Technology Park 176 Properties
Adagio Teas 146 Properties
Skokie Theatre 144 Properties
Illinois Holocaust Museum and Education Center 133 Properties
Niles Township 54 Properties

Frequently Asked Questions About Skokie?

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

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

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

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 71 properties listed in Skokie 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
Wildwood Vacation Rentals in Chicago, Illinois 141

People Also Ask

There are 71 Skokie, IL Vacation Rentals

Recently Booked Vacation Rentals in Skokie