66+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  4. Callicoon

Callicoon pickleball Stays, Resort Rentals, & Homes

About Callicoon Vacation Rentals

Discover over 66 amazing vacation rental options in Callicoon 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 Callicoon.

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 616.09 ft², with prices averaging US $414 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 Callicoon.

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Top Pickleball-Ready Accommodation Types in Callicoon

Type Count
Vacation Homes 46
Holiday Apartments 3
Cottages 2

Use these Quick Filters to Find a Vacation Rental in Callicoon

★ 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 Callicoon with PickleTrip™.

Weather in Callicoon, NY

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

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


Grover M. Hermann Hospital
Bethel Woods Center For The Arts
Resorts World Catskills
Monticello Casino and Raceway
Ski Big Bear at Masthope Mountain
Bethel Woods
White Sulphur Springs Synagogue
Wayne Memorial Hospital
Forestburgh Playhouse
Fort Delaware Museum
Upper Delaware Scenic and Recreational Area
Tarry Brae Golf Course
Honesdale Golf Club
Hancock Golf Course
Lake Superior
Sullivan County Dramatic Workshop - Rivoli Theatre
Concord Monster Golf Course
Carousel Water and Fun Park
Neversink Dam
Roscoe Presbyterian Church

Other Places to Stay in Callicoon, NY


Hankins 78 Properties
Hortonville 45 Properties
Grover M. Hermann Hospital 42 Properties
Town of Delaware 40 Properties

Frequently Asked Questions About Callicoon?

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

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

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

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 66 properties listed in Callicoon 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 66 Callicoon, NY Vacation Rentals

Recently Booked Vacation Rentals in Callicoon