Chepstow holiday cottages

Holiday cottages and self-catering accommodation in Chepstow

For a getaway in South Wales, take a look at our handpicked collection of holiday cottages in Chepstow. Known as the scenic gateway to Wales, Chepstow was once a medieval powerhouse and is now a modern and lively town that makes a great destination for a family holiday or a romantic getaway in a self-catering property. Adjoining the English border and at the southern tip of the Wye Valley Area of Outstanding Natural Beauty, Chepstow sits on the banks of the River Wye and is famous for its beautifully preserved stone castle. It’s also home to Chepstow Racecourse and is a ‘Walkers are Welcome’-accredited town – an ideal base for hiking long-distance trails such as the Wye Valley Walk, Offa’s Dyke National Trail and the Wales Coast Path.

Choose Chepstow as your base to explore Monmouthshire, an intriguing county that’s known as the food capital of Wales and is also a top spot for stargazing, with no less than five official Dark Sky Discovery Sites. The romantic ruins of Tintern Abbey are just 5 miles from Chepstow, and the extraordinary Puzzlewood, a unique and atmospheric ancient woodland, is 12 miles. A film location for both Star Wars and Doctor Who, this is somewhere the kids will definitely want to explore. Abergavenny, another mecca for foodies, is 23 miles away, at the foot of the Black Mountains, while the picturesque market town of Ross-on-Wye is 23.5 miles. For your perfect break in Monmouthshire, browse our complete range of Chepstow accommodation above.