98+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Virginia
  3. Winchester
  4. Ashby

Ashby pickleball Stays, Resort Rentals, & Homes

About Ashby Vacation Rentals

Discover over 98 amazing vacation rental options in Ashby 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 Ashby.

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 1022.21 ft², with prices averaging US $425 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 Ashby.

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Top Pickleball-Ready Accommodation Types in Ashby

Type Count
Vacation Homes 46
Cottages 8
Holiday Apartments 4
Villas 1

Use these Quick Filters to Find a Vacation Rental in Ashby

★ 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 Ashby with PickleTrip™.

Weather in Ashby, VA

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

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


SheNonedoah University
Front Royal Entrance SheNonedoah National Park
Winchester Medical Center
George Washington National Forest
Bluemont Vineyard
Summit Point Raceway
Skyline Caverns
Dinosaur Land
Apple Blossom Mall
Cobbler Mountain Cellars
SheNonedoah River State Park
Barrel Oak Winery
Linden Vineyards
Delaplane Cellars
Mt Hebron Cemetery
Jim Barnett Park
SheNonedoah Valley Discovery Museum
Wilson's Wild Animal Park
Virginia Wine Country Tours
Naked Mountain Winery & Vineyards

Frequently Asked Questions About Ashby?

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

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

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

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 98 properties listed in Ashby 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 98 Ashby, VA Vacation Rentals

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