1402+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Virginia
  3. Staunton
  4. Sherando

Sherando pickleball Stays, Resort Rentals, & Homes

About Sherando Vacation Rentals

Discover over 1402 amazing vacation rental options in Sherando 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 Sherando.

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 1132.86 ft², with prices averaging US $408 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 Sherando.

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Top Pickleball-Ready Accommodation Types in Sherando

Type Count
Vacation Homes 671
Holiday Apartments 96
Cottages 30
Villas 1

Use these Quick Filters to Find a Vacation Rental in Sherando

★ 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 Sherando with PickleTrip™.

Weather in Sherando, VA

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

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


Wintergreen Resort
Blue Ridge Parkway North Entrance
George Washington National Forest
Bold Rock Hard Cider Nellysford Cidery
Walton's Mountain Museum
Mary Baldwin College
Pippin Hill Farm & Vineyards
Rockfish Gap Entrance SheNonedoah
Afton Mountain Vineyards
Crabtree Falls
Sherando Lake Recreation Area
Frontier Culture Museum
Veritas Vineyard and Winery
Grand Caverns
The Woodrow Wilson Presidential Library
Starr Hill Brewery
Zeus Digital Theater
Cardinal Point Vineyard and Winery
Staunton Public Library
Wayne Theatre

Frequently Asked Questions About Sherando?

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

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

Discover 45 accommodations with private or nearby pickleball courts in Sherando. Some of the best destinations to stay and play pickleball are:

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

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

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 1402 properties listed in Sherando 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 1402 Sherando, VA Vacation Rentals

Recently Booked Vacation Rentals in Sherando