Chepstow stands where the Wye meets the Severn, at the bottom end of the valley and right on the border.
8 places to stay · showing 1–8
Chepstow, Wye Valley
A historic former 16th-century coaching inn in the heart of Chepstow, blending period charm with modern comforts.
Chepstow, Wye Valley
A truly unique romantic cottage for two in Chepstow — the town’s last surviving 13th-century town gate, a Grade II* listed building.
Chepstow, Wye Valley
A grand country house manor resort near Chepstow — a 14th-century manor in 400 acres of parkland, with golf and leisure.
Chepstow, Wye Valley
A single-storey barn near Chepstow, on the edge of the Wye Valley and Forest of Dean, sleeping 4 across two en-suite bedrooms, with a private hot…
Chepstow, Wye Valley
A 4-star barn conversion at Devauden near Chepstow, in the Wye Valley, sleeping 6 across three en-suite bedrooms, with panoramic views over the Vale of Usk.
Chepstow, Wye Valley
A detached single-storey lodge for two at Shirenewton near Chepstow, in the Wye Valley, dog-friendly with use of a five-acre field, uninterrupted rural views and a…
Chepstow, Wye Valley
A charming 5-star single-storey barn conversion in the peaceful village of Wolvesnewton near Chepstow, sleeping 2. Dog-friendly.
Chepstow, Wye Valley
A large Grade II listed holiday home at Shirenewton near Chepstow, sleeping 16 — a grand base for big family gatherings.
More places to stay nearby in Wye Valley
Ross on Wye, Wye Valley
A luxury 5-star 16th-century barn conversion near Ross-on-Wye, sleeping 8, combining elegance with seclusion.
Wye Valley
A charming, beautifully restored 14th-century inn in the heart of Ross-on-Wye — a traditional, central Wye Valley base.
Hay on Wye, Wye Valley
A traditional pub with rooms in the heart of Hay-on-Wye — a lively hub for locals and visitors, and a characterful base.
Monmouth, Wye Valley
A delightful 5-star semi-detached stone cottage on a working farm near Monmouth, sleeping 6, full of rustic character. Dog-friendly.
Wye Valley
A characterful 4-star restaurant with rooms in a 14th-century building near Ross-on-Wye in the Wye Valley.
Monmouth, Wye Valley
A charming, spacious 16th-century former farmhouse B&B at Mitchel Troy near Monmouth, awarded AA 3 Diamonds.
Wye Valley
A charming, beautifully restored 5-star holiday cottage near Ross-on-Wye, sleeping 6, in a peaceful borders location. Dog-friendly.
Ross on Wye, Wye Valley
A premier 5-star glamping destination on the slopes of May Hill near Ross-on-Wye, sleeping up to 16 — traditional camping with modern comforts. Dog-friendly.
The castle is the reason the town is here. It sits on a limestone cliff directly above the river, and it was begun in 1067, the year after the Conquest.
The Severn bridges and the M4 are a few minutes away, which makes this the easiest corner of the valley to reach from England.
Chepstow Castle is the oldest stone fortification still standing in Britain from after the Romans left. William FitzOsbern, one of the Conqueror's men, began it in 1067, the year after the Normans invaded.
Almost every castle of that age was thrown up in timber first and rebuilt in stone later. This one was stone from the start, and the great tower was finished by about 1090.
The thing to look for is the doors. The gatehouse still has its original pair, and tree-ring dating puts the timber somewhere between 1159 and 1189. They have been hanging in that gateway for over eight hundred years and most people walk straight past them.
The castle sits on a limestone cliff with the river directly below, which is the whole reason it is where it is. The town runs uphill behind it, and the Town Gate still stands across the western end of the High Street.
That gate was once the only way into Chepstow by land. Roger Bigod walled the town between 1272 and 1278, three-quarters of a mile of it. That was partly for defence and partly so that everyone coming to market paid at one door.
This was a working port for centuries, sending out oak and bark and bringing in wine from Gascony, Spain and Portugal. The tide helped and hindered in equal measure: between high and low the river here drops almost fifteen metres, one of the biggest ranges anywhere in the world.
Offa's Dyke Path begins just outside the town at Sedbury Cliffs and runs 177 miles north to Prestatyn. You can walk the first mile of it and be back for lunch, which a lot of people do.
Tintern is six miles up the valley and Monmouth about sixteen. The Severn bridges and the M4 are a few minutes the other way, which makes this the easiest corner of the valley to reach.
The Wye meets the Severn at Chepstow, under a castle begun in 1067. Prices start at about £80 a night. Tintern is six miles up the valley, Monmouth about sixteen, and Offa's Dyke Path starts at Sedbury Cliffs on the edge of town. See the whole Wye Valley.
See all: Wye Valley accommodation
Browse Wye Valley by type: B&Bs & Guest Houses · Hotels & Inns · Cottages & Self-Catering
Nearby towns: Hay-on-Wye · Monmouth · Tintern · Usk
Nearby areas: South Wales · Brecon Beacons
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