94+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  3. Cunningham

Cunningham pickleball Stays, Resort Rentals, & Homes

About Cunningham Vacation Rentals

Discover over 94 amazing vacation rental options in Cunningham 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 Cunningham.

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 779.52 ft², with prices averaging US $488 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 Cunningham.

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Top Pickleball-Ready Accommodation Types in Cunningham

Type Count
Vacation Homes 47
Cottages 17
Holiday Apartments 13

Use these Quick Filters to Find a Vacation Rental in Cunningham

★ 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 Cunningham with PickleTrip™.

Weather in Cunningham, VA

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

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


Layz S Ranch
University of Virginia
Monticello
Downtown Mall
John Paul Jones Arena
University of Virginia Hospital
Trump Winery
The Jefferson Theater
Barboursville Vineyards
Walton's Mountain Museum
Paramount Theater
Charlottesville Pavilion
Pippin Hill Farm & Vineyards
Scott Stadium
Keswick Vineyards and Winery
Michie Tavern
Fashion Square Mall
University Hall at University of Virginia
Jefferson Vineyards
Arcady Vineyard
Glentivar Plantation
Corner district
Barracks Road Shopping Center
Goochland Drive-In Theater
Carter Mountain Orchard
Rivanna Trails
Migration: A Gallery
Rotunda
Bear Creek Lake State Park
Albemarle County Court House

Other Places to Stay in Cunningham, VA


Layz S Ranch 78 Properties
Palmyra 67 Properties

Frequently Asked Questions About Cunningham?

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

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

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

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 94 properties listed in Cunningham 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 94 Cunningham, VA Vacation Rentals

Recently Booked Vacation Rentals in Cunningham