Castles
Base yourself at Penterry Holidays and you’re perfectly placed to explore some of the most atmospheric castles in Wales. From clifftop strongholds to fairytale towers, these historic sites are all easy day trips from Orchard Cottage and Anne’s Retreat.
Chepstow Castle
Just a short drive from Penterry, Chepstow Castle is one of the great medieval fortresses of Britain. Perched high above the River Wye, it’s thought to be the oldest surviving stone castle in the UK.
Why visit
- Dramatic clifftop setting overlooking the Wye
- Remarkably preserved stonework and towering walls
- Insight into Norman and medieval life
Stroll the ramparts, explore the great hall and enjoy river views – especially beautiful in the late afternoon light.
Practical details
For opening times, ticket prices and current events, visit the official Cadw page for Chepstow Castle: cadw.gov.wales.
Caldicot Castle & Country Park
Set in 55 acres of tranquil parkland, Caldicot Castle combines history with a relaxed, countryside feel – ideal if you’d like a gentler day out.
Why visit
- Picturesque castle set within a large country park
- Peaceful walks, picnic spots and wildlife
- Occasional events, markets and re-enactments
It’s a lovely option if you want to mix a bit of heritage with a leisurely stroll and perhaps a picnic before heading back to your secluded retreat.
Practical details
Check the official MonLife page for seasonal opening, parking and events: monlife.co.uk.
Raglan Castle
Raglan Castle feels almost theatrical, with its grand gatehouse, soaring towers and wide courtyard. Built later than many Welsh castles, it has a more “palatial” feel – part fortress, part showpiece home.
Why visit
- Striking Tudor-period ruins with impressive towers
- Romantic, photogenic setting – great for a leisurely explore
- Wonderful countryside views from the ramparts
Climb the towers, cross the moat and take your time soaking up the atmosphere before returning to the peace of Penterry.
Practical details
For visitor information and current opening times, see the Cadw page for Raglan Castle: cadw.gov.wales.
Make Penterry Your Castle Base
From Penterry Holidays, you can easily combine a castle or two with a riverside walk, a pub lunch or a quiet evening by the wood-burner. Whether you’re a history enthusiast or simply love atmospheric places with a view, Chepstow, Caldicot and Raglan castles offer memorable days out – all within easy reach of your secluded Wye Valley hideaway.