72+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Virginia
  3. Pennington Gap

Pennington Gap pickleball Stays, Resort Rentals, & Homes

About Pennington Gap Vacation Rentals

Discover over 72 amazing vacation rental options in Pennington Gap 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 Pennington Gap.

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 321.12 ft², with prices averaging US $197 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 Pennington Gap.

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Top Pickleball-Ready Accommodation Types in Pennington Gap

Type Count
Vacation Homes 25
Holiday Apartments 6
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Pennington Gap

★ 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 Pennington Gap with PickleTrip™.

Weather in Pennington Gap, VA

View the weather forecast for Pennington Gap before booking your Pennington Gap 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 Pennington Gap, VA

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


Cave Spring Park
Jefferson National Forest
Cherokee Reservoir
Black Mountain
Elrod Falls
Harlan Appalachian Regional Healthcare Hospital
Natural Tunnel State Park
Crooked Road Heritage Music Trail
Martins Fork Lake - Smith Recreation Area
Southwest Virginia Museum
Kingdom Come State Park
Rapid River Lodge & Water Park
The Harlan Center
Black Mountain Offroad Adventure Area - Putney Trailhead
Smith Recreation Area Beach
The Trail of the Lonesome Pine Outdoor Drama
Miner's Park
Lonesome Pine Hospital
Hancock County Hospital

Other Places to Stay in Pennington Gap, VA


Cave Spring Park 54 Properties
Ben Hur 53 Properties

Frequently Asked Questions About Pennington Gap?

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

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

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

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 72 properties listed in Pennington Gap 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 72 Pennington Gap, VA Vacation Rentals

Recently Booked Vacation Rentals in Pennington Gap