82+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Philipstown pickleball Stays, Resort Rentals, & Homes

About Philipstown Vacation Rentals

Discover over 82 amazing vacation rental options in Philipstown 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 Philipstown.

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 817.48 ft², with prices averaging US $660 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 Philipstown.

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Top Pickleball-Ready Accommodation Types in Philipstown

Type Count
Vacation Homes 60
Cottages 9
Holiday Apartments 5

Use these Quick Filters to Find a Vacation Rental in Philipstown

★ 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 Philipstown with PickleTrip™.

Weather in Philipstown, NY

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

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


Highlands Country Club
Garrison Golf Club
Boscobel House and Gardens
Constitution Marsh Audubon Center and Sanctuary
Hudson Highlands State Park
Garrison Art Center
Graymoor - The Holy Mountain
Foundry Dock Park
Manitoga The Russel Wright Design Center
Stonecrop Gardens
Chapel Restoration
Constitution Island
West Point Foundry Preserve
Little Stony Point Park
Putnam History Museum
Woodbury Common Premium Outlets
Bear Mountain State Park
United States Military Academy
Marist College
Vassar College

Other Places to Stay in Philipstown, NY


Graymoor - The Holy Mountain 77 Properties
Highlands Country Club 73 Properties
Manitoga The Russel Wright Design Center 72 Properties
Garrison Art Center 71 Properties
Constitution Marsh Audubon Center and Sanctuary 59 Properties
Garrison Golf Club 59 Properties
Constitution Island 57 Properties
Chapel Restoration 50 Properties
Foundry Dock Park 50 Properties
Garrison 36 Properties
Nelsonville 30 Properties
Cold Spring 28 Properties

Frequently Asked Questions About Philipstown?

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

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

Discover 2 accommodations with private or nearby pickleball courts in Philipstown. Some of the best destinations to stay and play pickleball are:

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

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

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 82 properties listed in Philipstown 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.


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There are 82 Philipstown, NY Vacation Rentals

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