37+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Kentucky
  3. Lexington
  4. Winchester

Winchester pickleball Stays, Resort Rentals, & Homes

About Winchester Vacation Rentals

Discover over 37 amazing vacation rental options in Winchester 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 Winchester.

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 759.87 ft², with prices averaging US $158 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 Winchester.

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Top Pickleball-Ready Accommodation Types in Winchester

Type Count
Vacation Homes 15
Holiday Apartments 4

Use these Quick Filters to Find a Vacation Rental in Winchester

★ 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 Winchester with PickleTrip™.

Weather in Winchester, KY

View the weather forecast for Winchester before booking your Winchester 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 Winchester, KY

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


Clark Regional Medical Center
Bluegrass Heritage Museum
Lykins Park
Community Park
Southwind Golf Course
Cassell Creek Golf Course
Rupp Arena
University of Kentucky
Kentucky Horse Park
Red River Gorge
Keeneland Racing Course
Fayette Mall
Kroger Field
University of Kentucky Albert B. Chandler Hospital
Natural Bridge State Park
The Mall At Lexington Green
Lexington Opera House
Lexington Convention Center
Eastern Kentucky University
Hamburg Place

Other Places to Stay in Winchester, KY


Clark County 45 Properties
Cassell Creek Golf Course 31 Properties
Southwind Golf Course 29 Properties
Bluegrass Heritage Museum 28 Properties
Lykins Park 27 Properties
Community Park 27 Properties
Clark Regional Medical Center 27 Properties

Frequently Asked Questions About Winchester?

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

How many PickleTrip vacation rentals or resorts are available in Winchester?

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 37 properties listed in Winchester 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 37 Winchester, KY Vacation Rentals

Recently Booked Vacation Rentals in Winchester