Upperville pickleball Stays, Resort Rentals, & Homes
About Upperville Vacation Rentals
Discover over 52 amazing vacation rental options in Upperville 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 Upperville.
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 1327.72 ft², with prices averaging US $636 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 Upperville.
Top Pickleball-Ready Accommodation Types in Upperville
| Type | Count |
|---|---|
| Vacation Homes | 28 |
| Cottages | 9 |
| Villas | 2 |
| Holiday Apartments | 1 |
Use these Quick Filters to Find a Vacation Rental in Upperville
★ 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 Upperville with PickleTrip™.
Weather in Upperville, VA
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Top Attractions Around Upperville, VA
PickleTrip offers a large selection of top attractions around Upperville . Research things to do on your vacation before you visit Upperville.
Frequently Asked Questions About Upperville?
What are the top vacation rentals, resorts, and hotels in Upperville 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 Upperville. 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 Upperville!
- The Mill House in Upperville -
- Blue Mountain Log Cabin
- Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!
- 18th Century Stone Cottage minutes from historic Middleburg
- Lovely Guest House 2.5 miles from downtown Middleburg
- Historic house in Upperville! Wineries, equestrian events, great location!
- Hunt Country cottage in Upperville!
- Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More
- Cozy Country Getaway in the Heart of Upperville
- Renovated 1880s farmhouse near the Blue Ridge and Sky Meadows with amazing views
Which vacation rentals, resorts, or hotels in Upperville is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Upperville? 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.
- Charming 3-Bedroom Farmhouse In Virginia Horse & Wine Country
- Guest House at Mt. Independence
- Cozy, Pet-friendly Cottage in the Middleburg Wine region
How many PickleTrip vacation rentals or resorts are available in Upperville?
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 52 properties listed in Upperville in 2026, 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.
