26+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Virginia
  3. Gwynn

Gwynn pickleball Stays, Resort Rentals, & Homes

About Gwynn Vacation Rentals

Discover over 26 amazing vacation rental options in Gwynn 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 Gwynn.

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 1205.23 ft², with prices averaging US $392 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 Gwynn.

Show more
Show less

Top Pickleball-Ready Accommodation Types in Gwynn

Type Count
Vacation Homes 22
Cottages 3

Use these Quick Filters to Find a Vacation Rental in Gwynn

★ 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 Gwynn with PickleTrip™.

Weather in Gwynn, VA

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

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


Gwynn's Island Musuem
Deltaville Marina
Rosewell Ruins
Deltaville Maritime Museum
Chatham Vineyards
White Stone Beach
Good Luck Cellars
Holly Point Nature Park
Gloucester Museum of History
Bethel Beach
Golden Eagle Golf Club
Middlesex County Museum
Savage Neck Dunes Natural Area Preserve
The Dog and Oyster Vineyard
Historic Christ Church
Hughlett Point Natural Area
Steamboat Era Museum
Bethel Beach Natural Area Preserve
Riverside Walter Reed Hospital

Other Places to Stay in Gwynn, VA


Gwynn's Island Musuem 80 Properties

Frequently Asked Questions About Gwynn?

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

How many PickleTrip vacation rentals or resorts are available in Gwynn?

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 26 properties listed in Gwynn 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 26 Gwynn, VA Vacation Rentals

Recently Booked Vacation Rentals in Gwynn