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Woodbury pickleball Stays, Resort Rentals, & Homes

About Woodbury Vacation Rentals

Discover over 106 amazing vacation rental options in Woodbury 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 Woodbury.

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 616.25 ft², with prices averaging US $728 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 Woodbury.

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Top Pickleball-Ready Accommodation Types in Woodbury

Type Count
Vacation Homes 63
Villas 12
Cottages 5
Holiday Apartments 1

Use these Quick Filters to Find a Vacation Rental in Woodbury

★ 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 Woodbury with PickleTrip™.

Weather in Woodbury, NY

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

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


Woodbury Common Premium Outlets
Old Glory Mall Shopping Center
Palaia Vineyards Winery
Lake Tiorati Beach
Bear Mountain State Park
United States Military Academy
Campgaw Mountain Ski Area
Palisades Center
Dia Beacon
Storm King Art Center
Westchester Broadway Theatre
Tarrytown Music Hall
Mount Peter Ski Area
Brotherhood Winery
Nyack College
SplashDown Beach
Harriman State Park
Governor Mario M. Cuomo Bridge
Ramapo College of New Jersey
Lyndhurst Mansion

Other Places to Stay in Woodbury, NY


Lake Tiorati Beach 42 Properties
Highland Mills 40 Properties
Palaia Vineyards Winery 39 Properties
Woodbury Common Premium Outlets 29 Properties
Central Valley 26 Properties
Old Glory Mall Shopping Center 26 Properties
Harriman 24 Properties

Frequently Asked Questions About Woodbury?

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

How many pickleball-ready properties have private pools in Woodbury?

Discover 5 accommodations with private or nearby pickleball courts in Woodbury. Some of the best destinations to stay and play pickleball are:

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

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

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 106 properties listed in Woodbury 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 106 Woodbury, NY Vacation Rentals

Recently Booked Vacation Rentals in Woodbury