3127+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Skylands Region

Skylands Region pickleball Stays, Resort Rentals, & Homes

About Skylands Region Vacation Rentals

Discover over 3127 amazing vacation rental options in Skylands Region 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 Skylands Region.

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 913.89 ft², with prices averaging US $383 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 Skylands Region.

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Top Pickleball-Ready Accommodation Types in Skylands Region

Type Count
Vacation Homes 1478
Holiday Apartments 349
Cottages 61
Villas 49

Use these Quick Filters to Find a Vacation Rental in Skylands Region

★ 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 Skylands Region with PickleTrip™.

Weather in Skylands Region, US

View the weather forecast for Skylands Region before booking your Skylands Region 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 Skylands Region, US

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


Bushkill Falls
Mountain Creek Ski Resort
Princeton University
Shawnee Mountain Ski Area
Crystal Springs Golf Resort
Rutgers New Brunswick
East Stroudsburg University
Peddler's Village
Rutgers University
Delaware Water Gap National Recreation Area
Mountain Creek Waterpark
Sherman Theater
Pocono Mountains Visitors Bureau
Mall at Short Hills
Morristown Memorial Hospital
Turtle Back Zoo
The Funplex
South Mountain Reservation
New Jersey Convention and Exposition Center
Palmer Square

Other Places to Stay in Skylands Region, US


East Stroudsburg 497 Properties
Middle Smithfield Township 495 Properties
Somerset 451 Properties
Union County 432 Properties
Middlesex County 392 Properties
Parsippany 285 Properties
Sussex County 277 Properties
Morris County 195 Properties
Passaic County 192 Properties
Smithfield Township 176 Properties
Shawnee On Delaware 175 Properties
Somerset County 160 Properties

Frequently Asked Questions About Skylands Region?

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

How many pickleball-ready properties have private pools in Skylands Region?

Discover 222 accommodations with private or nearby pickleball courts in Skylands Region. Some of the best destinations to stay and play pickleball are:

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

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

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 3127 properties listed in Skylands Region 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.

Nearby Neighborhood (11) 
Neighborhood Property Count
Downtown Historic District Vacation Rentals in Skylands Region, US 25
Lake Mohawk Vacation Rentals in Skylands Region, US 96
Kendall Park Vacation Rentals in Skylands Region, US 41
West Caldwell Vacation Rentals in Skylands Region, US 242
South Side Vacation Rentals in Skylands Region, US 44
Green Pond Vacation Rentals in Skylands Region, US 498
Oak Ridge Vacation Rentals in Skylands Region, US 485
North Caldwell Vacation Rentals in Skylands Region, US 53
Murray Hill Vacation Rentals in Skylands Region, US 49
Pocono Mountain Lake Estates Vacation Rentals in Skylands Region, US 43
Convent Station Vacation Rentals in Skylands Region, US 42

People Also Ask

There are 3127 Skylands Region, US Vacation Rentals

Recently Booked Vacation Rentals in Skylands Region