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

About Oswego Vacation Rentals

Discover over 73 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 554.11 ft², with prices averaging US $226 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 34
Holiday Apartments 21
Cottages 1

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, NY

View the weather forecast for Oswego before booking your Oswego 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 Oswego, NY

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


State University of New York-Oswego
Oswego Speedway
Oswego Country Club
Breitbeck Park
Wright's Landing Marina
Scriba Town Park
Fort Ontario State Historic Site
Richardson-Bates House Museum
Salmon River
Fair Haven Beach State Park
Salmon River Fish Hatchery
Fulton Speedway
Southwick Beach State Park
Oneida Shores Park
Sodus Bay
Thunder Island
Radisson Greens Golf Club
Salmon River Falls
Brewerton Speedway
Beaver Lake Nature Center

Other Places to Stay in Oswego, NY


Scriba Town Park 58 Properties
Town of Scriba 57 Properties
Minetto 52 Properties
Oswego Speedway 51 Properties
Richardson-Bates House Museum 44 Properties
Wright's Landing Marina 44 Properties
Fort Ontario State Historic Site 43 Properties
Breitbeck Park 43 Properties
State University of New York-Oswego 42 Properties
Oswego Country Club 41 Properties
Lycoming 35 Properties
New Haven 27 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 Oswego? 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 73 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.


People Also Ask

There are 73 Oswego, NY Vacation Rentals

Recently Booked Vacation Rentals in Oswego