130+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. New York
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  4. Peekskill

Peekskill pickleball Stays, Resort Rentals, & Homes

About Peekskill Vacation Rentals

Discover over 130 amazing vacation rental options in Peekskill 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 Peekskill.

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 769.89 ft², with prices averaging US $402 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 Peekskill.

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Top Pickleball-Ready Accommodation Types in Peekskill

Type Count
Vacation Homes 77
Holiday Apartments 19
Cottages 14

Use these Quick Filters to Find a Vacation Rental in Peekskill

★ 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 Peekskill with PickleTrip™.

Weather in Peekskill, NY

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

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


Paramount Hudson Valley Theater
Peekskill Landing Park
Blue Mountain Reservation
Hudson Valley Center for Contemporary Art
Depew Park
Charles Point Pier Park
Peekskill Museum
Lincoln Depot Museum
Woodbury Common Premium Outlets
Bear Mountain State Park
United States Military Academy
Palisades Center
Westchester County Center
Purchase College
Dia Beacon
Storm King Art Center
Westchester Broadway Theatre
Tarrytown Music Hall
Mount Peter Ski Area
The Westchester Mall

Other Places to Stay in Peekskill, NY


Hudson Valley Center for Contemporary Art 46 Properties
Lincoln Depot Museum 41 Properties
Depew Park 40 Properties
Blue Mountain Reservation 40 Properties
Peekskill Museum 39 Properties
Paramount Hudson Valley Theater 39 Properties
Peekskill Landing Park 39 Properties
Charles Point Pier Park 38 Properties

Frequently Asked Questions About Peekskill?

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

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

Discover 3 accommodations with private or nearby pickleball courts in Peekskill. Some of the best destinations to stay and play pickleball are:

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

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

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 130 properties listed in Peekskill 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 130 Peekskill, NY Vacation Rentals

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