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

About Oswego Vacation Rentals

Discover over 71 amazing vacation rental options in Oswego 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 Oswego.

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 893.53 ft², with prices averaging $303 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 Oswego.

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Top Pickleball-Ready Accommodation Types in Oswego

Type Count
Vacation Homes 45
Holiday Apartments 14
Cottages 2

Use these Quick Filters to Find a Vacation Rental in Oswego

★ 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 Oswego with PickleTrip™.

Weather in Oswego, IL

View the weather forecast for Oswego before booking your Oswego Vacation Rentals to confirm your best time to go.

December - February
High 47°F       Low 28°F
March - May
High 70°F       Low 41°F
June - August
High 87°F       Low 55°F
September - November
High 78°F       Low 42°F

Top Attractions Around Oswego, IL

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


Hudson Crossing Park
Fox Valley Winery
Route 66 Raceway
Chicago Premium Outlets
Wheaton College
Morton Arboretum
Hollywood Casino Joliet
Hollywood Casino Aurora
Arcada Theater
Raging Waves Waterpark
Rialto Square Theater
Harrah's Casino
Paramount Theater
Chicagoland Speedway
Bolingbrook Golf Club
Yorktown Shopping Center
Hollywood Casino
Joliet Junior College
Lewis University
iPic Theaters

Other Places to Stay in Oswego, IL


Fox Valley Winery 98 Properties
Montgomery 30 Properties
Hudson Crossing Park 26 Properties

Frequently Asked Questions About Oswego?

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

Which vacation rentals, resorts, or hotels in Oswego 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 Oswego?

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 Oswego 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.


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There are 71 Oswego, IL Vacation Rentals

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