63+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  3. Chestertown

Chestertown pickleball Stays, Resort Rentals, & Homes

About Chestertown Vacation Rentals

Discover over 63 amazing vacation rental options in Chestertown 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 Chestertown.

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 935.77 ft², with prices averaging US $530 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 Chestertown.

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Top Pickleball-Ready Accommodation Types in Chestertown

Type Count
Vacation Homes 41
Holiday Apartments 9
Cottages 3

Use these Quick Filters to Find a Vacation Rental in Chestertown

★ 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 Chestertown with PickleTrip™.

Weather in Chestertown, MD

View the weather forecast for Chestertown before booking your Chestertown Vacation Rentals to confirm your best time to go.

December - February
High 56°F       Low 33°F
March - May
High 73°F       Low 38°F
June - August
High 90°F       Low 69°F
September - November
High 80°F       Low 42°F

Top Attractions Around Chestertown, MD

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


Washington College
Wilmer Park
Rolphs Wharf Marina
Historical Society of Kent County Maryland
River Arts Chestertown
Garfield Center for the Arts at the Prince Theater
U.S. Naval Academy
Ripken Stadium
White Marsh Mall
Chesapeake Bay Bridge
Fort McHenry
Sandy Point State Park
Canton Waterfront Park
Queenstown Premium Outlets
Annapolis Maritime Museum
Queenstown Harbor Golf Club
Liriodendron Mansion
Havre de Grace Promenade
Bay Hills Golf Club
Maryland World War II Memorial

Other Places to Stay in Chestertown, MD


Kent County 172 Properties
Great Oak Landing 147 Properties
Georgetown 137 Properties
Tolchester Beach 66 Properties
Pomona 48 Properties
Fairlee 43 Properties
Wilmer Park 40 Properties
River Arts Chestertown 40 Properties
Garfield Center for the Arts at the Prince Theater 40 Properties
Historical Society of Kent County Maryland 40 Properties
Washington College 40 Properties
Rolphs Wharf Marina 27 Properties

Frequently Asked Questions About Chestertown?

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

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

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

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 63 properties listed in Chestertown 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 63 Chestertown, MD Vacation Rentals

Recently Booked Vacation Rentals in Chestertown