41+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Indiana
  3. Hagerstown

Hagerstown pickleball Stays, Resort Rentals, & Homes

About Hagerstown Vacation Rentals

Discover over 41 amazing vacation rental options in Hagerstown 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 Hagerstown.

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 749.38 ft², with prices averaging US $190 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 Hagerstown.

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Top Pickleball-Ready Accommodation Types in Hagerstown

Type Count
Vacation Homes 25
Holiday Apartments 9

Use these Quick Filters to Find a Vacation Rental in Hagerstown

★ 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 Hagerstown with PickleTrip™.

Weather in Hagerstown, IN

View the weather forecast for Hagerstown before booking your Hagerstown 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 Hagerstown, IN

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


Abbott's Candy Shop
Earlham College
Richmond Art Museum
Richmond Mall
Winchester Golf Club
New Castle Motorsports Park
Richmond Civic Theatre
Glenn Miller Park
Depot District
Prairie Creek Reservoir and Campground
Rose Garden
Warm Glow Candle Company
Whitewater Valley Railroad
Joseph Moore Museum
Connersville Community Flea Market
Wayne County Historical Museum
Westwood Park
Hayes Arboretum
Veterans Memorial Park
Wayne County Fairgrounds

Other Places to Stay in Hagerstown, IN


Abbott's Candy Shop 40 Properties

Frequently Asked Questions About Hagerstown?

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

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

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 41 properties listed in Hagerstown 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 41 Hagerstown, IN Vacation Rentals

Recently Booked Vacation Rentals in Hagerstown