859+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Orange County pickleball Stays, Resort Rentals, & Homes

About Orange County Vacation Rentals

Discover over 859 amazing vacation rental options in Orange County 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 Orange County.

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 953.1 ft², with prices averaging US $479 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 Orange County.

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Top Pickleball-Ready Accommodation Types in Orange County

Type Count
Vacation Homes 472
Holiday Apartments 145
Villas 41
Cottages 37

Use these Quick Filters to Find a Vacation Rental in Orange County

★ 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 Orange County with PickleTrip™.

Weather in Orange County, NY

View the weather forecast for Orange County before booking your Orange County 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 Orange County, NY

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


Woodbury Common Premium Outlets
United States Military Academy
Storm King Art Center
Mount Peter Ski Area
Brotherhood Winery
Mount Saint Mary's College Newburgh
Orange County Choppers
Frederick Franck's Pacem in Terris
Warwick Valley Winery and Distillery
Paramount Theatre
Bear Mountain State Park
Chadwick Lake Park
Algonquin Park
Orange County Fairgrounds
Upper Delaware River
ANoneda Ashram
Tuxedo Ridge Ski Center
Galleria at Crystal Run
Michie Stadium
West Point Museum
Cronomer Hill Park
Monroe Federal Plaza Shopping Center
National Purple Heart Hall of Honor
Motorcyclepedia Museum
New York Military Academy
Goshen Historic Track
Ritz Theater
Washington Headquarters
Sterling Forest State Park
Thomas Bull Memorial Park

Other Places to Stay in Orange County, NY


Newburgh 547 Properties
Woodbury 121 Properties
Sparrow Bush 53 Properties
Monroe 52 Properties
Town of Highlands 46 Properties
Greenwood Lake 42 Properties
Highland Falls 41 Properties
Town of Deerpark 38 Properties
Warwick 38 Properties
Middletown 35 Properties
Goshen 33 Properties
Montgomery 24 Properties

Frequently Asked Questions About Orange County?

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

How many pickleball-ready properties have private pools in Orange County?

Discover 75 accommodations with private or nearby pickleball courts in Orange County. Some of the best destinations to stay and play pickleball are:

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

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

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 859 properties listed in Orange County 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.


People Also Ask

There are 859 Orange County, NY Vacation Rentals

Recently Booked Vacation Rentals in Orange County