Annapolis County pickleball Stays, Resort Rentals, & Homes
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Luxury Places to Stay in Annapolis County
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Top-Rated Villas with a Pool in Annapolis County
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Pet-Friendly Villas in Annapolis County
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Large Private Villas in Annapolis County
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Annapolis County Villas, Airbnb and Holiday Homes Under $200
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Instantly Bookable Villa Rentals in Annapolis County
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Book a Last Minute Place to Stay in Annapolis County
About Annapolis County Vacation Rentals
Discover over 97 amazing vacation rental options in Annapolis County 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 County.
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 436.16 ft², with prices averaging $163 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 County.
Top Pickleball-Ready Accommodation Types in Annapolis County
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Vacation Homes | 30 |
Cottages | 21 |
Holiday Apartments | 8 |
Villas | 1 |
Use these Quick Filters to Find a Vacation Rental in Annapolis County
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★ 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 County with PickleTrip™.
Weather in Annapolis County, NS
View the weather forecast for Annapolis County before booking your Annapolis County Vacation Rentals to confirm your best time to go.
Top Attractions Around Annapolis County, NS
PickleTrip offers a large selection of top attractions around Annapolis County . Research things to do on your vacation before you visit Annapolis County.
Other Places to Stay in Annapolis County, NS
Frequently Asked Questions About Annapolis County?
What are the top vacation rentals, resorts, and hotels in Annapolis County 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 County. 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 County!
- Grand Oak Manor Bed & Breakfast
- The Lark & Loon Inn
- Come Stay in Historic Downtown Annapolis Royal!
- Still Point Lodge & Cottages
- Bear River Vineyards
- Oceanfront oasis located in historical Annapolis Royal.
- Beautiful hilltop cottage, stunning views, 5 mins. to town
- The Little Red Cottage
- Lakefront Retreat With Sandy Beach, Perfect For Kids
- Rare Private Apartment in Annapolis Royal
Which vacation rentals, resorts, or hotels in Annapolis County is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in ? 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.
- Campground style living in country setting.
- Carleton Inn and Cottages
- Come Stay in Historic Downtown Annapolis Royal!
How many PickleTrip vacation rentals or resorts are available in Annapolis County?
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 97 properties listed in Annapolis County 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.