208+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Annapolis pickleball Stays, Resort Rentals, & Homes

About Annapolis Vacation Rentals

Discover over 208 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 1361.72 ft², with prices averaging US $493 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 199
Cottages 3

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, CA

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

December - February
High 56°F       Low 27°F
March - May
High 72°F       Low 34°F
June - August
High 89°F       Low 62°F
September - November
High 79°F       Low 36°F

Top Attractions Around Annapolis, CA

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


Sonoma Coast State Park
Dry Creek Vineyard
Manchester Beach
Fort Ross State Historic Park
Gualala River
Korbel Champagne Cellars
Armstrong Redwoods State Park
Black Point Beach
Pebble Beach
A Touch of Heaven Massage Therapy
Gualala Point Regional Park
Goat Rock Beach
Bohemian Grove
Point Arena Lighthouse & Museum
Salt Point State Park
B. Bryan Preserve
Jenner Beach
Arena Cove and Pier
Johnson's Beach

Other Places to Stay in Annapolis, CA


Stewarts Point 250 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!

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 208 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.


People Also Ask

There are 208 Annapolis, CA Vacation Rentals

Recently Booked Vacation Rentals in Annapolis