314+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  3. Chester County

Chester County pickleball Stays, Resort Rentals, & Homes

About Chester County Vacation Rentals

Discover over 314 amazing vacation rental options in Chester County 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 Chester County.

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 883.59 ft², with prices averaging US $297 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 Chester County.

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Top Pickleball-Ready Accommodation Types in Chester County

Type Count
Vacation Homes 132
Holiday Apartments 52
Cottages 14
Villas 3

Use these Quick Filters to Find a Vacation Rental in Chester County

★ 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 Chester County with PickleTrip™.

Weather in Chester County, PA

View the weather forecast for Chester County before booking your Chester County 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 Chester County, PA

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


Longwood Gardens
West Chester University of Pennsylvania
Valley Forge Casino
Valley Forge Convention Center
Brandywine Valley
Valley Forge National Historic Park
Exton Square Mall
QVC Studio Park
Dowington Country Club
Chaddsford Winery
September Farm Cheese
Marsh Creek State Park
Wyncote Golf Club
Victory Brewing Company
Phoenixville Farmers Market
Phoenixville Taste
People's Light
Anson B. Nixon Park
Play-A-Round Golf
Brandywine Picnic Park
Baldwin's Book Barn
J. Maki Winery
Hopewell Furnace National Historic Site
Freedoms Foundation
American Helicopter Museum and Education Center
Pennsbury-Chadds Ford Antique Mall
Daylesford Abbey
Loch Nairn Golf Club
World of Scouting Museum
The Mill at Anselma

Other Places to Stay in Chester County, PA


Exton 155 Properties
Honey Brook 86 Properties
Wayne 82 Properties
Brandywine Valley 72 Properties
Tredyffrin Township 54 Properties
Kennett Township 34 Properties
Kennett Square 32 Properties
Phoenixville 32 Properties
West Chester 29 Properties
West Whiteland Township 28 Properties
Malvern 28 Properties
Pottstown 27 Properties

Frequently Asked Questions About Chester County?

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

How many pickleball-ready properties have private pools in Chester County?

Discover 18 accommodations with private or nearby pickleball courts in Chester County. Some of the best destinations to stay and play pickleball are:

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

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

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 314 properties listed in Chester County in 2026, 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 314 Chester County, PA Vacation Rentals

Recently Booked Vacation Rentals in Chester County