102+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  3. Fairplay

Fairplay pickleball Stays, Resort Rentals, & Homes

About Fairplay Vacation Rentals

Discover over 102 amazing vacation rental options in Fairplay 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 Fairplay.

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 747.95 ft², with prices averaging US $268 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 Fairplay.

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Top Pickleball-Ready Accommodation Types in Fairplay

Type Count
Vacation Homes 50
Holiday Apartments 8
Cottages 6

Use these Quick Filters to Find a Vacation Rental in Fairplay

★ 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 Fairplay with PickleTrip™.

Weather in Fairplay, MD

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

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


Whitetail Ski Resort
Hollywood Casino at Charles Town Races
Harpers Ferry National Historical Park
Hagerstown Premium Outlets
Catoctin Mountain Park
Hagerstown Speedway
Antietam National Battlefield
Maryland Theater
Fort Detrick
Greenbrier State Park
Shepherd University
Big Cork Vineyards
Antietam National Cemetery
Cunningham Falls State Park
Greencastle Coffee Roasters
For the Kids
Appalachian Trail Conservancy Headquarters
Catoctin Wildlife Preserve and Zoo
Blue Ridge Center for Environmental Stewardship
Charles Town Library

Frequently Asked Questions About Fairplay?

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

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

Discover 1 accommodations with private or nearby pickleball courts in Fairplay. Some of the best destinations to stay and play pickleball are:

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

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

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 102 properties listed in Fairplay 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 102 Fairplay, MD Vacation Rentals

Recently Booked Vacation Rentals in Fairplay