374+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Virginia
  3. Cape Charles
  4. Cheriton

Cheriton pickleball Stays, Resort Rentals, & Homes

About Cheriton Vacation Rentals

Discover over 374 amazing vacation rental options in Cheriton 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 Cheriton.

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 766.18 ft², with prices averaging US $437 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 Cheriton.

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Top Pickleball-Ready Accommodation Types in Cheriton

Type Count
Vacation Homes 315
Holiday Apartments 12
Cottages 6
Villas 2

Use these Quick Filters to Find a Vacation Rental in Cheriton

★ 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 Cheriton with PickleTrip™.

Weather in Cheriton, VA

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

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


Cape Charles Beach
Chesapeake Bay Bridge-Tunnel
Barrier Islands Center
Kiptopeke State Park
Eastern Shore of Virginia National Wildlife Refuge
Bay Creek Golf Club
Northampton Shopping Center
Chatham Vineyards
Barrier Island Museum
Eyre Hall
Cape Charles Museum & Welcome Center
Holly Grove Vineyards
Bethel Beach
Savage Neck Dunes Natural Area Preserve
John Custis' Tomb
Bethel Beach Natural Area Preserve

Frequently Asked Questions About Cheriton?

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

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

Discover 6 accommodations with private or nearby pickleball courts in Cheriton. Some of the best destinations to stay and play pickleball are:

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

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

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 374 properties listed in Cheriton 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.


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There are 374 Cheriton, VA Vacation Rentals

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