123+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. United Kingdom
  2. Wales
  3. Cardiff
  4. Chepstow

Chepstow pickleball Stays, Resort Rentals, & Homes

About Chepstow Vacation Rentals

Discover over 123 amazing vacation rental options in Chepstow 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 Chepstow.

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 478.78 ft², with prices averaging US $278 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 Chepstow.

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Top Pickleball-Ready Accommodation Types in Chepstow

Type Count
Vacation Homes 55
Cottages 32
Holiday Apartments 12
Villas 2

Use these Quick Filters to Find a Vacation Rental in Chepstow

★ 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 Chepstow with PickleTrip™.

Weather in Chepstow, GB

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

December - February
High 43°F       Low 32°F
March - May
High 61°F       Low 36°F
June - August
High 63°F       Low 48°F
September - November
High 58°F       Low 35°F

Top Attractions Around Chepstow, GB

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


Chepstow Racecourse
Tintern Abbey
Chepstow Castle
Saint Pierre Park
Chepstow Museum
Symonds Yat Rock
Gate House
Parva Farm Vineyard
Forest of Dean
Cardiff Motorpoint Arena
Cardiff Bay
Bristol Hippodrome Theatre
University of Bristol
Cardiff Castle
Clifton Suspension Bridge
Wales Millennium Centre
Cardiff University
Wye Valley
We The Curious

Other Places to Stay in Chepstow, GB


Tintern Abbey 77 Properties
Symonds Yat Rock 73 Properties
Chepstow Museum 71 Properties
Parva Farm Vineyard 71 Properties
Chepstow Castle 70 Properties
Chepstow Racecourse 69 Properties
Tidenham 67 Properties
Tintern 61 Properties
Trelleck Grange 61 Properties
Mathern 53 Properties
Earlswood 42 Properties
Llanvair Discoed 24 Properties

Frequently Asked Questions About Chepstow?

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

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

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

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 123 properties listed in Chepstow in 2026, 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.


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There are 123 Chepstow, GB Vacation Rentals

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