84+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Illinois
  3. Chicago
  4. Uptown

Uptown pickleball Stays, Resort Rentals, & Homes

About Uptown Vacation Rentals

Discover over 84 amazing vacation rental options in Uptown 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 Uptown.

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 881.53 ft², with prices averaging US $248 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 Uptown.

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Top Pickleball-Ready Accommodation Types in Uptown

Type Count
Holiday Apartments 62
Vacation Homes 10

Use these Quick Filters to Find a Vacation Rental in Uptown

★ 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 Uptown with PickleTrip™.

Weather in Uptown, IL

View the weather forecast for Uptown before booking your Uptown 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

Other Places to Stay in Uptown, IL


Graceland Cemetery 1,273 Properties
Sheridan Park 1,255 Properties
Our Lady of Lourdes Church 1,244 Properties
About Face Theater 1,212 Properties
Buena Park 1,207 Properties
Essanay Studios 1,204 Properties
Pegasus Players 1,202 Properties
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Methodist Hospital of Chicago 1,192 Properties
Aragon Ballroom 1,186 Properties
Aragon Entertainment Center 1,181 Properties
Hutchinson Street District 1,159 Properties

Frequently Asked Questions About Uptown?

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

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

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

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 Uptown 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 (8) 
Neighborhood Property Count
Lakeview Vacation Rentals in Chicago, Illinois 266
Edgewater Vacation Rentals in Chicago, Illinois 78
Ravenswood Vacation Rentals in Chicago, Illinois 33
Edgewater Beach Vacation Rentals in Chicago, Illinois 30
Andersonville Vacation Rentals in Chicago, Illinois 1110
Lakewood-Balmoral Vacation Rentals in Chicago, Illinois 1081
Buena Park Vacation Rentals in Chicago, Illinois 1207
Sheridan Park Vacation Rentals in Chicago, Illinois 1255

People Also Ask

There are 84 Uptown, IL Vacation Rentals

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