120+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Virginia
  3. Chincoteague
  4. Deep Hole

Deep Hole pickleball Stays, Resort Rentals, & Homes

About Deep Hole Vacation Rentals

Discover over 120 amazing vacation rental options in Deep Hole 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 Deep Hole.

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 215.92 ft², with prices averaging US $321 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 Deep Hole.

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Top Pickleball-Ready Accommodation Types in Deep Hole

Type Count
Vacation Homes 116
Cottages 2

Use these Quick Filters to Find a Vacation Rental in Deep Hole

★ 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 Deep Hole with PickleTrip™.

Weather in Deep Hole, VA

View the weather forecast for Deep Hole before booking your Deep Hole 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 Deep Hole, VA

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


Chincoteague National Wildlife Refuge
Wallops Flight Facility
Assateague Point
Museum of Chincoteague
Bloxom Winery
Assateague Lighthouse
Pocomoke River State Park
Pocomoke River Canoe Company
Cypress Park
Delmarva Discovery Center
Oyster Bay
Kegotank Bay
Robert N. Reed Downtown Waterfront Park
Nassawango Golf Course
Bishop's Stock Fine Art
Coventry Parish Ruins
Julia A. Purnell Museum
Captain Timothy Hill House
Maui Jack's Waterpark

Frequently Asked Questions About Deep Hole?

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

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

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

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 120 properties listed in Deep Hole 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.


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There are 120 Deep Hole, VA Vacation Rentals

Recently Booked Vacation Rentals in Deep Hole