37+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Virginia
  3. Luray
  4. Skyland

Skyland pickleball Stays, Resort Rentals, & Homes

About Skyland Vacation Rentals

Discover over 37 amazing vacation rental options in Skyland 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 Skyland.

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 1304.18 ft², with prices averaging US $349 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 Skyland.

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Top Pickleball-Ready Accommodation Types in Skyland

Type Count
Vacation Homes 11
Cottages 6

Use these Quick Filters to Find a Vacation Rental in Skyland

★ 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 Skyland with PickleTrip™.

Weather in Skyland, VA

View the weather forecast for Skyland before booking your Skyland Vacation Rentals to confirm your best time to go.

December - February
High 56°F       Low 24°F
March - May
High 73°F       Low 31°F
June - August
High 87°F       Low 58°F
September - November
High 80°F       Low 32°F

Top Attractions Around Skyland, VA

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


Luray Caverns
SheNonedoah Caverns
Little Washington Winery
Swift Run Gap Entrance SheNonedoah
Old Rag Mountain
Skyland
Luray Zoo - A Rescue Zoo
Thorton Gap Entrance SheNonedoah
New Market Battlefield
Yogi Bear's Jellystone Park
Early Mountain Vineyards
Rose River Falls
SheNonedoah River State Park
The Garden Maze at Luray Caverns
Meems Bottom Covered Bridge
Verity Blue
Rapidan Camp
Dukes of Hazzard Museum
Luray Valley Museum
Mary's Rock Summit Trailhead

Frequently Asked Questions About Skyland?

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

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

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

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 37 properties listed in Skyland 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 37 Skyland, VA Vacation Rentals

Recently Booked Vacation Rentals in Skyland