269+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. New York
  3. Kingston
  4. Round Top

Round Top pickleball Stays, Resort Rentals, & Homes

About Round Top Vacation Rentals

Discover over 269 amazing vacation rental options in Round Top 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 Round Top.

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 1128.4 ft², with prices averaging US $512 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 Round Top.

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Top Pickleball-Ready Accommodation Types in Round Top

Type Count
Vacation Homes 166
Holiday Apartments 9
Cottages 9
Villas 5

Use these Quick Filters to Find a Vacation Rental in Round Top

★ 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 Round Top with PickleTrip™.

Weather in Round Top, NY

View the weather forecast for Round Top before booking your Round Top 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 Round Top, NY

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


Blackhead Mountain Country Club
Hunter Mountain
Windham Mountain Resort
Catskill Mountains
Kaaterskill Falls
Bard College
Copperhood Retreat & Spa
Saugerties Lighthouse
Olana State Historic Site
Hudson Valley Mall
Windham Vineyards and Winery
Windham Country Club
Zoom Flume
Emerson Place Kaleidoscope
Bethel Woods Museum
Opus 40
The Clermont Mansion
Hudson Opera House
Van Alen House
Esopus Bend Nature Preserve

Other Places to Stay in Round Top, NY


Blackhead Mountain Country Club 29 Properties

Frequently Asked Questions About Round Top?

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

How many pickleball-ready properties have private pools in Round Top?

Discover 9 accommodations with private or nearby pickleball courts in Round Top. Some of the best destinations to stay and play pickleball are:

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

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

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 269 properties listed in Round Top 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 269 Round Top, NY Vacation Rentals

Recently Booked Vacation Rentals in Round Top