Chepstow Travel Guide

Tourist Guide

The ruins of a large, historic stone building with multiple arches and a tall, narrow tower.
An ancient stone structure with arched walkways and a grassy courtyard.
The ruins of a medieval stone structure with arched doorways and a tall bell tower.
The interior of an ancient stone structure with arched doorways and columns.
An ancient stone archway with a staircase leading into a lush green landscape.

Nestled in an almost signature ‘S’ bend of theRiver Wye is the attractive market town of Chepstowin the Welsh county of Monmouthshire. With Gloucestershire just over theborder, Bristol a short drive away and Newport just down the road Chepstowis ideally located for exploring the southwest of England and the surroundingWelsh countryside but there are plenty of other reasons to plan a break in Chepstow.

On theRiver Wye

For a start there’s its rather delightful locationas the River Wye snakes its way to join the River Severn just a couple of milesdownstream. The western end of the Severn Bridge links the town withneighbouring Gloucestershire and makes an iconic sight as it reaches across theriver to join Wales and England.

ChepstowCastle

And, of course, there’s that dramatic castleoverlooking the town like a domineering but protective patriarch. The magnificentNorman castle at Chepstow perches on top of alimestone cliff that hangs over the river, and guards the main river crossing.Miraculously intact this is actually one of the oldest castles in Britain,dating all the way back to the Norman Conquest, and the impressive Great Tower stillfeatures its original architecture.

ChepstowMuseum

You can learn all about the castle’s history in themuseum that is housed in the Lower Bailey and to bring your understanding of Chepstow’shistory up to date you can nip across the road from the castle into the 18thcentury town house in which a kid-friendly museum brings the town’s industrial andsocial history to life.

If its myth and legend that you are after then Chepstowcan provide you with plenty of romantic legends too. It is said that a cave inthe cliff underneath the castle is where King Arthur and his trusty knights areresting and conserving their powers until the next time that Britain needssaving from dark forces.

Chepstow Shops

The name Chepstowderives from the old English ‘chepe stowe’ which means market place or tradingcentre. The town centre today has over 130 shops within easy walking distance andthe pedestrianised St Mary's Street contains antique shops, craft and giftshops, cafes and restaurants.

Festivalsin Chepstow

Markets and festivals still define the rhythms ofthe weeks and changing of the seasons here. The ChepstowFarmer’s market is held on the second and fourth Saturday of every month andthe Chepstow Show draws farmers from miles aroundto display their wares and compete for prizes every August. Meanwhile in Julythe Two Rivers Folk Festival offers three days of music and dance and there isthe Chepstow Festival packed with medievalre-enactments, pageantry and drama.

ChepstowRacecourse

For those partial to a flutter you are in the righttown: ChepstowRacecourse is the leading horse racing course in Wales. You will findit on the edge of the town, in the grounds of the ruined Piercefield House. Theracecourse itself was first opened in 1926, and has held the Welsh National since1949.

VisitChepstow

With its stunning but centrallocation, historical sights and contemporary shopping, hotels and restaurants,river views and racecourse excitement, Chepstowoffers an ideal place to explore Wales and Southwest England.

Where to stay in Chepstow

Find the best Chepstow areas for the activities you enjoy most. Learn more about Chepstow
Learn more about Chepstow

Caerwent

Caerwent is noteworthy for its bars, and you can make a stop at top attractions like Caerwent Roman Town and Dewstow Golf Club.

Delta Hotels by Marriott St. Pierre Country Club

Delta Hotels by Marriott St. Pierre Country Club

4 out of 5
St Pierre Park Chepstow Wales
The price is £93 per night from 13 Nov to 14 Nov
£93
13 Nov - 14 Nov
includes taxes & fees
Stay at this golf hotel in Chepstow. Enjoy free Wi-Fi, free parking and a golf course. Our guests praise the helpful staff and the clean rooms in their reviews. ...
8.2/10 Very good! (1,003 reviews)
"Fabulous hotel in a beautiful setting and grounds. A little on the pricey side but worth it to mark or celebrate a special occasion. A good base from which to go out exploring, or to take in a round of golf right there on the doorstep. Would recommend and indeed return."

Reviewed on 3 Nov 2026

Delta Hotels by Marriott St. Pierre Country Club
Clayton Hotel Bristol City

Clayton Hotel Bristol City

4 out of 5
Broad Street Bristol England
The price is £86 per night from 8 Nov to 9 Nov
£86
8 Nov - 9 Nov
includes taxes & fees
Stay at this business-friendly hotel in Bristol. Enjoy free Wi-Fi, breakfast (surcharge) and 24-hour room service. Our guests praise the breakfast and the helpful ...
Clayton Hotel Bristol City
Celtic Manor Resort

Celtic Manor Resort

5 out of 5
Chepstow Road Newport Wales
The price is £129 per night from 27 Nov to 28 Nov
£129
27 Nov - 28 Nov
includes taxes & fees
Stay at this luxury hotel in Newport. Enjoy free Wi-Fi, 2 indoor pools and a full-service spa. Our guests praise the breakfast and the helpful staff in their ...
8.6/10 Excellent! (1,448 reviews)
"The signature rooms are very nice - spacious and with a balcony. Love the lounge and the good breakfast at Steak on Six. Sona was good for dinner, with superbly attentive staff, but it was a little overpriced. Our air con didn’t work and the pool changing rooms could do with a freshen up, but otherwise ..."

Reviewed on 1 Nov 2026

Celtic Manor Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Wallhope Retreat - Chepstow, spectacular views

Wallhope Retreat - Chepstow, spectacular views

Chepstow Gloucestershire
Stay at this cottage in Chepstow. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Wye Valley and Symonds Yat Rock are located nearby.
10/10 Exceptional! (40 reviews)
Perfect
"Very comfortable and welcoming accommodation in a beautiful setting. Sarah and team ensured we got the most out of our stay, thank you."

Reviewed on 30 Oct 2026

Wallhope Retreat - Chepstow, spectacular views
Cleyro Serviced Apartments-Finzels Reach

Cleyro Serviced Apartments-Finzels Reach

3.5 out of 5
Finzels Reach, Unit R01, Malt House Bristol England
Stay at this apartment in Bristol. Enjoy free Wi-Fi, parking (surcharge) and laundry facilities. Popular attractions Cabot Circus Shopping Centre and Bristol ...
9.4/10 Exceptional! (109 reviews)
"Well located, very courteous host and flawless check in. Scaffolding and work noise in the window without price reduction."

Reviewed on 22 Oct 2026

Cleyro Serviced Apartments-Finzels Reach
 Park Lane Aparthotel

Park Lane Aparthotel

4 out of 5
23-24 Park Place Cardiff Wales
Stay at this apartment in Cardiff. Enjoy free Wi-Fi, meeting facilities and housekeeping. Popular attractions Cardiff Castle and Utilita Arena Cardiff are located ...
7.6/10 Good! (91 reviews)
"Great location, easy to walk to city centre."

Reviewed on 25 Oct 2026

Park Lane Aparthotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Chepstow attractions

Things to do

Cities near Chepstow

Explore a world of travel with Expedia