411+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Dickerson pickleball Stays, Resort Rentals, & Homes

About Dickerson Vacation Rentals

Discover over 411 amazing vacation rental options in Dickerson 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 Dickerson.

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 735.78 ft², with prices averaging US $279 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 Dickerson.

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Top Pickleball-Ready Accommodation Types in Dickerson

Type Count
Vacation Homes 180
Holiday Apartments 77
Cottages 25
Villas 6

Use these Quick Filters to Find a Vacation Rental in Dickerson

★ 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 Dickerson with PickleTrip™.

Weather in Dickerson, MD

View the weather forecast for Dickerson before booking your Dickerson 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 Dickerson, MD

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


Sugarloaf Mountain Park
Sugarloaf Mountain Vineyard
Reston Town Center
Tysons Corner Center
National Air and Space Museum Steven F. Udvar-Hazy Center
Wolf Trap National Park for the Performing Arts
Walter Reed National Military Medical Center
Rockville Town Center
Harpers Ferry National Historical Park
RIO Washingtonian Center
Dulles Town Center
National Institute of Health Campus
Leesburg Corner Premium Outlets
Tysons Galleria
Great Falls Park
One Loudoun
Stone Tower Winery
Reston Hospital Center
Westview Promenade
Dulles Expo Conference Center

Other Places to Stay in Dickerson, MD


Sugarloaf Mountain Vineyard 388 Properties
Comus 30 Properties
Sugarloaf Mountain Park 26 Properties

Frequently Asked Questions About Dickerson?

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

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

Discover 15 accommodations with private or nearby pickleball courts in Dickerson. Some of the best destinations to stay and play pickleball are:

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

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

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 411 properties listed in Dickerson 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 411 Dickerson, MD Vacation Rentals

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