92+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. New York
  3. Monticello
  4. Town of Highland

Town of Highland pickleball Stays, Resort Rentals, & Homes

About Town of Highland Vacation Rentals

Discover over 92 amazing vacation rental options in Town of Highland 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 Town of Highland.

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 822.4 ft², with prices averaging US $495 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 Town of Highland.

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Top Pickleball-Ready Accommodation Types in Town of Highland

Type Count
Vacation Homes 52
Cottages 11
Holiday Apartments 4

Use these Quick Filters to Find a Vacation Rental in Town of Highland

★ 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 Town of Highland with PickleTrip™.

Weather in Town of Highland, NY

View the weather forecast for Town of Highland before booking your Town of Highland 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 Town of Highland, NY

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


Brook House Gallery Incorporated
Minisink Battlefield County Park
Eagle Institute
Minisink Battleground Park
Lake Wallenpaupack
Bethel Woods Center For The Arts
Resorts World Catskills
Delaware Water Gap National Recreation Area
Monticello Casino and Raceway
Ski Big Bear at Masthope Mountain
Bethel Woods
High Point State Park
Holiday Mountain Ski and Fun Park
Promised Land State Park
White Sulphur Springs Synagogue
Dingmans Falls
Wayne Memorial Hospital
Forestburgh Playhouse
Upper Delaware River
George W. Childs Park

Other Places to Stay in Town of Highland, NY


Minisink Battlefield County Park 86 Properties
Minisink Battleground Park 75 Properties
Barryville 45 Properties
Yulan 43 Properties
Eagle Institute 40 Properties
Brook House Gallery Incorporated 40 Properties
Highland Lake 31 Properties
Eldred 24 Properties

Frequently Asked Questions About Town of Highland?

What are the top vacation rentals, resorts, and hotels in Town of Highland 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 Town of Highland. 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 Town of Highland!

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

Looking for a fun and active getaway with pickleball courts in Town of Highland? 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 Town of Highland?

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 92 properties listed in Town of Highland 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 92 Town of Highland, NY Vacation Rentals

Recently Booked Vacation Rentals in Town of Highland