Chester pickleball Stays, Resort Rentals, & Homes
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Luxury Places to Stay in Chester
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Top-Rated Villas with a Pool in Chester
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Pet-Friendly Villas in Chester
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Large Private Villas in Chester
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Chester Villas, Airbnb and Holiday Homes Under $200
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Instantly Bookable Villa Rentals in Chester
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Book a Last Minute Place to Stay in Chester
About Chester Vacation Rentals
Discover over 54 amazing vacation rental options in Chester 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 Chester.
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 800.82 ft², with prices averaging $356 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 Chester.
Top Pickleball-Ready Accommodation Types in Chester
Type | Count |
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Vacation Homes | 35 |
Cottages | 11 |
Holiday Apartments | 5 |
Villas | 1 |
Use these Quick Filters to Find a Vacation Rental in Chester
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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 Chester with PickleTrip™.
Weather in Chester, NS
View the weather forecast for Chester before booking your Chester Vacation Rentals to confirm your best time to go.
Top Attractions Around Chester, NS
PickleTrip offers a large selection of top attractions around Chester . Research things to do on your vacation before you visit Chester.
Other Places to Stay in Chester, NS
Frequently Asked Questions About Chester?
What are the top vacation rentals, resorts, and hotels in Chester 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 Chester. 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 Chester!
- Serenity Tiny House Cottage in Chester
- Cooperage Cottage - Peaceful & Family Friendly, Oceanfront
- Ahoy!.Oceanfront Family Cottage with Hot Tub, Near South Shore Attractions
- Custom Built Home On The Scenic Waterfront Facing The Picturesque MarriottsCove
- Gorgeous Oceanfront Estate with Heated Pool
- The Lower Deck Oceanfront Studio mins from Chester and beaches
- The Captain’s Quarters 2 bedroom harbourview condo
- Seascape,Art Deco cottage
- The Chester House, oceanside in the village, private wharf
- White Cottage, An East Coast Architectural Masterpiece
Which vacation rentals, resorts, or hotels in Chester 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.
- Ahoy!.Oceanfront Family Cottage with Hot Tub, Near South Shore Attractions
- Home in the Heart of Chester
- 2700’ | Waterviews | 2Levels | Walk to DT | Office
How many PickleTrip vacation rentals or resorts are available in Chester?
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 54 properties listed in Chester 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.