61+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. New York
  3. White Plains
  4. Ossining

Ossining pickleball Stays, Resort Rentals, & Homes

About Ossining Vacation Rentals

Discover over 61 amazing vacation rental options in Ossining 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 Ossining.

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 1131.06 ft², with prices averaging US $610 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 Ossining.

Show more
Show less

Top Pickleball-Ready Accommodation Types in Ossining

Type Count
Vacation Homes 36
Holiday Apartments 10
Cottages 5
Villas 1

Use these Quick Filters to Find a Vacation Rental in Ossining

★ 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 Ossining with PickleTrip™.

Weather in Ossining, NY

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

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


Sing Sing Correctional Facility
Thomas J. Watson Research Center
Sing Sing Prison Museum
Teatown Lake Reservation
Hudson Hills Golf Course
Ossining Historical Society
Nelson Park
Louis Engel Waterfront Park
Merchants Square
Pleasant Square
Snowden Avenue Park
Depot Square
Kitchawan Preserve
Woodbury Common Premium Outlets
Bear Mountain State Park
United States Military Academy
Capitol Theatre
Campgaw Mountain Ski Area
Empire City Casino
Palisades Center

Other Places to Stay in Ossining, NY


Nelson Park 94 Properties
Sing Sing Correctional Facility 91 Properties
Louis Engel Waterfront Park 88 Properties
Depot Square 85 Properties
Pleasant Square 77 Properties
Sing Sing Prison Museum 77 Properties
Snowden Avenue Park 77 Properties
Merchants Square 76 Properties
Ossining Historical Society 56 Properties
Maryknoll 51 Properties
Hudson Hills Golf Course 47 Properties
Teatown Lake Reservation 46 Properties

Frequently Asked Questions About Ossining?

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

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

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

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 61 properties listed in Ossining 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 61 Ossining, NY Vacation Rentals

Recently Booked Vacation Rentals in Ossining