1992+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Williamsburg pickleball Stays, Resort Rentals, & Homes

About Williamsburg Vacation Rentals

Discover over 1992 amazing vacation rental options in Williamsburg 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 Williamsburg.

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 581.14 ft², with prices averaging US $234 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 Williamsburg.

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Top Pickleball-Ready Accommodation Types in Williamsburg

Type Count
Holiday Apartments 118
Vacation Homes 118
Villas 42
Cottages 6

Use these Quick Filters to Find a Vacation Rental in Williamsburg

★ 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 Williamsburg with PickleTrip™.

Weather in Williamsburg, VA

View the weather forecast for Williamsburg before booking your Williamsburg 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 Williamsburg, VA

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


Busch Gardens Williamsburg
Colonial Williamsburg
Water Country USA
Colonial Williamsburg Visitor Center
Jamestown Settlement
Williamsburg Winery
College of William and Mary
Williamsburg Premium Outlets
Historic Jamestowne
Ripley's Believe It or Not!
Colonial National Historical Park
Merchants Square
Governor's Palace
Ford's Colony at Williamsburg
Bear Track Landing
Williamsburg Botanical Garden
Kingsmill Plantation Golf Course
Greensprings Greenway Interpretative Trail
Carter's Grove Plantation
Freedom Park

Other Places to Stay in Williamsburg, VA


James City County 1,565 Properties
Busch Tennis Courts 1,399 Properties
College of William and Mary 1,394 Properties
Cary Stadium 1,379 Properties
Muscarelle Museum of Art 1,331 Properties
Walter J. Zable Stadium at Cary Field 1,292 Properties
Colonial National Historical Park 316 Properties
Berkeley 168 Properties
Lightfoot 165 Properties
Stonehouse 54 Properties
Norge 52 Properties
Kingsmill 38 Properties

Frequently Asked Questions About Williamsburg?

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

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

Discover 317 accommodations with private or nearby pickleball courts in Williamsburg. Some of the best destinations to stay and play pickleball are:

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

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

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 1992 properties listed in Williamsburg 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 (2) 
Neighborhood Property Count
North Newport News Vacation Rentals in Williamsburg, Virginia 139
Kingsmill Vacation Rentals in Williamsburg, Virginia 38

People Also Ask

There are 1992 Williamsburg, VA Vacation Rentals

Recently Booked Vacation Rentals in Williamsburg