1594+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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West Side pickleball Stays, Resort Rentals, & Homes

About West Side Vacation Rentals

Discover over 1594 amazing vacation rental options in West Side 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 West Side.

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 772.6 ft², with prices averaging $354 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 West Side.

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Top Pickleball-Ready Accommodation Types in West Side

Type Count
Holiday Apartments 1109
Vacation Homes 225
Villas 2

Use these Quick Filters to Find a Vacation Rental in West Side

★ 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 West Side with PickleTrip™.

Weather in West Side, IL

View the weather forecast for West Side before booking your West Side 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 West Side, IL

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


Union Station
United Center
University of Illinois Chicago
Douglas Park
UIC Pavilion
Rush University Medical Center
Humboldt Park
Union Park
Garfield Park Conservatory
Chicago Arts District
National Museum of Mexican Art
Garfield Park
Old St Patrick’s Church
Flat Iron Building
Maxwell Street Market
Holy Innocents Church
Addams/Medill Park
Canalport Riverwalk Park
Paseo Boricua
St. Basil Greek Orthodox Church

Other Places to Stay in West Side, IL


Near West Side 361 Properties
West Town 315 Properties
West Loop 205 Properties
East Village 154 Properties
University Village / Little Italy 113 Properties
River West 53 Properties
Lower West Side 51 Properties
Wicker Park 50 Properties
Pulaski Park 40 Properties
Noble Square 40 Properties
Heart of Chicago 38 Properties
Tri-Taylor 26 Properties

Frequently Asked Questions About West Side?

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

How many pickleball-ready properties have private pools in West Side?

Discover 6 accommodations with private or nearby pickleball courts in West Side. Some of the best destinations to stay and play pickleball are:

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

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

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 1594 properties listed in West Side 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 (16) 
Neighborhood Property Count
Downtown Chicago Vacation Rentals in Chicago, Illinois 1703
Near North Side Vacation Rentals in Chicago, Illinois 785
The Loop Vacation Rentals in Chicago, Illinois 713
River North Vacation Rentals in Chicago, Illinois 434
Near West Side Vacation Rentals in Chicago, Illinois 361
West Town Vacation Rentals in Chicago, Illinois 315
West Loop Vacation Rentals in Chicago, Illinois 205
Lincoln Park Vacation Rentals in Chicago, Illinois 158
University Village / Little Italy Vacation Rentals in Chicago, Illinois 113
Logan Square Vacation Rentals in Chicago, Illinois 78
Wicker Park Vacation Rentals in Chicago, Illinois 50
Bucktown Vacation Rentals in Chicago, Illinois 27
Austin Vacation Rentals in Chicago, Illinois 159
Chinatown Vacation Rentals in Chicago, Illinois 3053
North Lawndale Vacation Rentals in Chicago, Illinois 443
Illinois Medical District Vacation Rentals in Chicago, Illinois 3502

People Also Ask

There are 1594 West Side, IL Vacation Rentals

Recently Booked Vacation Rentals in West Side