26440+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Chesapeake Bay

Chesapeake Bay pickleball Stays, Resort Rentals, & Homes

About Chesapeake Bay Vacation Rentals

Discover over 26440 amazing vacation rental options in Chesapeake Bay 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 Chesapeake Bay.

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 741.87 ft², with prices averaging US $335 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 Chesapeake Bay.

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Top Pickleball-Ready Accommodation Types in Chesapeake Bay

Type Count
Vacation Homes 11009
Holiday Apartments 7423
Cottages 609
Villas 274

Use these Quick Filters to Find a Vacation Rental in Chesapeake Bay

★ 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 Chesapeake Bay with PickleTrip™.

Weather in Chesapeake Bay, US

View the weather forecast for Chesapeake Bay before booking your Chesapeake Bay 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 Chesapeake Bay, US

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


White House
Busch Gardens Williamsburg
National Mall
Virginia Beach Boardwalk
Washington Monument
National Aquarium in Baltimore
Colonial Williamsburg
Walter E. Washington Convention Center
George Washington University
Arlington National Cemetery
Smithsonian National Air and Space Museum
Naval Station Norfolk
Lincoln Memorial
Baltimore Cruise Terminal
University of Maryland-College Park
Johns Hopkins University
Capital One Arena
United States Capitol
Baltimore Convention Center
National Museum of Natural History

Other Places to Stay in Chesapeake Bay, US


Maryland 16,551 Properties
Northern Chesapeake Bay 10,004 Properties
Washington 3,542 Properties
District of Columbia 3,412 Properties
Norfolk - Virginia Beach 3,079 Properties
Northwest 2,037 Properties
Virginia Beach 2,007 Properties
Anne Arundel County 1,423 Properties
Baltimore 1,407 Properties
Northeast Virginia Beach 1,159 Properties
Alanton 1,121 Properties
Arlington 1,077 Properties

Frequently Asked Questions About Chesapeake Bay?

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

How many pickleball-ready properties have private pools in Chesapeake Bay?

Discover 1306 accommodations with private or nearby pickleball courts in Chesapeake Bay. Some of the best destinations to stay and play pickleball are:

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

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

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 26440 properties listed in Chesapeake Bay in 2026, 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.

Nearby Neighborhood (16) 
Neighborhood Property Count
Northwest Vacation Rentals in Chesapeake Bay, US 2037
Northeast Virginia Beach Vacation Rentals in Chesapeake Bay, US 1159
Northeast Vacation Rentals in Chesapeake Bay, US 792
Capitol Hill Vacation Rentals in Chesapeake Bay, US 661
Downtown Washington D.C. Vacation Rentals in Chesapeake Bay, US 660
Downtown Baltimore Vacation Rentals in Chesapeake Bay, US 565
Crystal City Vacation Rentals in Chesapeake Bay, US 253
Dupont Circle Vacation Rentals in Chesapeake Bay, US 213
Rosslyn Vacation Rentals in Chesapeake Bay, US 194
Downtown Vacation Rentals in Chesapeake Bay, US 138
Old Town Alexandria Vacation Rentals in Chesapeake Bay, US 134
Fells Point Vacation Rentals in Chesapeake Bay, US 65
Georgetown Vacation Rentals in Chesapeake Bay, US 56
Foggy Bottom Vacation Rentals in Chesapeake Bay, US 49
Pentagon City Vacation Rentals in Chesapeake Bay, US 40
Chic's Beach Vacation Rentals in Chesapeake Bay, US 38

People Also Ask

There are 26440 Chesapeake Bay, US Vacation Rentals

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