264+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Virginia
  3. Charlottesville
  4. Roseland

Roseland pickleball Stays, Resort Rentals, & Homes

About Roseland Vacation Rentals

Discover over 264 amazing vacation rental options in Roseland 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 Roseland.

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 1315.95 ft², with prices averaging US $485 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 Roseland.

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Top Pickleball-Ready Accommodation Types in Roseland

Type Count
Vacation Homes 158
Cottages 10
Holiday Apartments 8
Villas 3

Use these Quick Filters to Find a Vacation Rental in Roseland

★ 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 Roseland with PickleTrip™.

Weather in Roseland, VA

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

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


Crabtree Falls
Woodson's Mill
Reids Gap Trailhead
Wintergreen Resort
Virginia Military Institute
Blue Ridge Parkway North Entrance
George Washington National Forest
Jefferson National Forest
Virginia Horse Center
Bold Rock Hard Cider Nellysford Cidery
Walton's Mountain Museum
Washington and Lee University
Mary Baldwin College
Pippin Hill Farm & Vineyards
Rockfish Gap Entrance SheNonedoah
Sweet Briar College
Afton Mountain Vineyards
Southern Virginia University
Sherando Lake Recreation Area
Frontier Culture Museum

Other Places to Stay in Roseland, VA


Reids Gap Trailhead 1,193 Properties
Chestnut Springs 85 Properties
Tyro 81 Properties
Crabtree Falls 66 Properties
Piney River 47 Properties
Woodson's Mill 40 Properties
Lowesville 39 Properties
Massies Mill 34 Properties

Frequently Asked Questions About Roseland?

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

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

Discover 2 accommodations with private or nearby pickleball courts in Roseland. Some of the best destinations to stay and play pickleball are:

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

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

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 264 properties listed in Roseland 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.

Nearby Neighborhood (3) 
Neighborhood Property Count
Chestnut Springs Vacation Rentals in Charlottesville, Virginia 85
Laurel Ridge Vacation Rentals in Charlottesville, Virginia 1312
Deer Springs Vacation Rentals in Charlottesville, Virginia 1281

People Also Ask

There are 264 Roseland, VA Vacation Rentals

Recently Booked Vacation Rentals in Roseland