187+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Chelston pickleball Stays, Resort Rentals, & Homes

About Chelston Vacation Rentals

Discover over 187 amazing vacation rental options in Chelston 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 Chelston.

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 1077.34 ft², with prices averaging US $614 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 Chelston.

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Top Pickleball-Ready Accommodation Types in Chelston

Type Count
Holiday Apartments 73
Vacation Homes 46
Cottages 11
Villas 1

Use these Quick Filters to Find a Vacation Rental in Chelston

★ 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 Chelston with PickleTrip™.

Weather in Chelston, BM

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

December - February
High 73°F       Low 56°F
March - May
High 74°F       Low 56°F
June - August
High 85°F       Low 72°F
September - November
High 83°F       Low 67°F

Top Attractions Around Chelston, BM

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


Horseshoe Bay
King's Wharf in Dockyard
Royal Naval Dockyard
Elbow Beach
Fairmont Southampton Golf Club
Warwick Long Bay
City Hall
Bermuda State House at St. George's
Bermuda Perfumery
Tobacco Bay
Crystal Caves
Fort Hamilton
Clearwater Beach
Mid Ocean Golf Club
Shelly Bay
Bermuda Aquarium Museum and Zoo
Tucker's Point Golf Club
Bermuda Botanical Gardens
St. Catherine's Beach
Port Royal Golf Course

Frequently Asked Questions About Chelston?

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

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

Discover 4 accommodations with private or nearby pickleball courts in Chelston. Some of the best destinations to stay and play pickleball are:

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

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

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 187 properties listed in Chelston 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 187 Chelston, BM Vacation Rentals

Recently Booked Vacation Rentals in Chelston