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Annapolis pickleball Stays, Resort Rentals, & Homes

About Annapolis Vacation Rentals

Discover over 1254 amazing vacation rental options in Annapolis 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 Annapolis.

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 981.84 ft², with prices averaging US $558 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 Annapolis.

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Top Pickleball-Ready Accommodation Types in Annapolis

Type Count
Vacation Homes 886
Holiday Apartments 128
Cottages 34
Villas 6

Use these Quick Filters to Find a Vacation Rental in Annapolis

★ 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 Annapolis with PickleTrip™.

Weather in Annapolis, MD

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

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


U.S. Naval Academy
Six Flags America
Westfield Annapolis Mall
Annapolis City Dock
Chesapeake Bay Bridge
Sandy Point State Park
Bowie State University
Anne Arundel Medical Center
Maryland State House
Navy-Marine Corps Memorial Stadium
Annapolis Harbour Center
Kunta Kinte–Alex Haley Memorial
Annapolis Maritime Museum
Allen Pond Park
Maryland Quiet Waters Park
St John's College
Bay Hills Golf Club
Maryland World War II Memorial
William Paca House
The Kunta Kinte Alex Haley Memorial

Other Places to Stay in Annapolis, MD


Northern Chesapeake Bay 12,995 Properties
Historic District 458 Properties
Kent Island 89 Properties
Parole 89 Properties
Bowie 84 Properties
Stevensville 71 Properties
Eastport 63 Properties
Edgewater 58 Properties
Selby-on-the-Bay 45 Properties
Lake Arbor 35 Properties
Cape Saint Claire 30 Properties
Arnold 26 Properties

Frequently Asked Questions About Annapolis?

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

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

Discover 59 accommodations with private or nearby pickleball courts in Annapolis. Some of the best destinations to stay and play pickleball are:

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

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

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 1254 properties listed in Annapolis 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.

Nearby Neighborhood (16) 
Neighborhood Property Count
Historic District Vacation Rentals in Annapolis, Maryland 458
Eastport Vacation Rentals in Annapolis, Maryland 63
Hillsmere Vacation Rentals in Annapolis, Maryland 24
Murray Hill Vacation Rentals in Annapolis, Maryland 24
Arundel on the Bay Vacation Rentals in Annapolis, Maryland 155
West Annapolis Vacation Rentals in Annapolis, Maryland 710
Homewood Vacation Rentals in Annapolis, Maryland 722
Epping Forest Vacation Rentals in Annapolis, Maryland 329
Atlantis Vacation Rentals in Annapolis, Maryland 89
Oyster Harbor Vacation Rentals in Annapolis, Maryland 220
Cape St. John Vacation Rentals in Annapolis, Maryland 176
Anchorage Vacation Rentals in Annapolis, Maryland 631
Hunt Meadows Vacation Rentals in Annapolis, Maryland 776
Kingsport Vacation Rentals in Annapolis, Maryland 737
Winchester-on-the-Severn Vacation Rentals in Annapolis, Maryland 505
Downs on the Severn Vacation Rentals in Annapolis, Maryland 149

People Also Ask

There are 1254 Annapolis, MD Vacation Rentals

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