868+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Monticello pickleball Stays, Resort Rentals, & Homes

About Monticello Vacation Rentals

Discover over 868 amazing vacation rental options in Monticello 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 Monticello.

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 839.78 ft², with prices averaging US $424 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 Monticello.

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Top Pickleball-Ready Accommodation Types in Monticello

Type Count
Vacation Homes 472
Holiday Apartments 54
Cottages 44
Villas 16

Use these Quick Filters to Find a Vacation Rental in Monticello

★ 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 Monticello with PickleTrip™.

Weather in Monticello, NY

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

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


Resorts World Catskills
Monticello Casino and Raceway
Holiday Mountain Ski and Fun Park
Forestburgh Playhouse
Straus Center - Frost Valley YMCA
Tarry Brae Golf Course
Hancock Golf Course
Sullivan County Dramatic Workshop - Rivoli Theatre
Concord Monster Golf Course
Red Hill Fire Tower
Mongaup Pond Campground
Shadowland Theater
Neversink Dam
Catskill Fly Fishing Center and Museum
Roscoe Presbyterian Church
Brook House Gallery Incorporated
South Fallsburg Hebrew Association Synagogue
Grossinger Country Club
Sullivan County Golf and Country Club
Hancock Riverpark

Other Places to Stay in Monticello, NY


The Catskills 4,462 Properties
Town of Thompson 113 Properties
Town of Colchester 104 Properties
Roscoe 87 Properties
Town of Rockland 64 Properties
Livingston Manor 64 Properties
Town of Highland 59 Properties
Hancock 46 Properties
Town of Delaware 40 Properties
Callicoon 40 Properties
Swan Lake 40 Properties
Parksville 36 Properties

Frequently Asked Questions About Monticello?

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

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

Discover 41 accommodations with private or nearby pickleball courts in Monticello. Some of the best destinations to stay and play pickleball are:

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

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

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 868 properties listed in Monticello 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 868 Monticello, NY Vacation Rentals

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