77+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  4. River West

River West pickleball Stays, Resort Rentals, & Homes

About River West Vacation Rentals

Discover over 77 amazing vacation rental options in River West 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 River West.

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 644.18 ft², with prices averaging US $393 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 River West.

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Top Pickleball-Ready Accommodation Types in River West

Type Count
Holiday Apartments 64
Vacation Homes 5

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

★ 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 River West with PickleTrip™.

Weather in River West, IL

View the weather forecast for River West before booking your River West 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

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Frequently Asked Questions About River West?

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

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

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

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 77 properties listed in River West 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 (6) 
Neighborhood Property Count
Downtown Chicago Vacation Rentals in Chicago, Illinois 1518
Near North Side Vacation Rentals in Chicago, Illinois 600
River North Vacation Rentals in Chicago, Illinois 315
West Town Vacation Rentals in Chicago, Illinois 313
Pulaski Park Vacation Rentals in Chicago, Illinois 34
Killgubbin Vacation Rentals in Chicago, Illinois 32

People Also Ask

There are 77 River West, IL Vacation Rentals

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