View Self-Catering Holiday Cottages in Chepstow

Chepstow on the River Wye in the South East corner of Wales's borders with England, and makes a fantastic impression as the first Welsh town visitors discover when crossing the Severn Bridge. Chepstow’s striking castle, the oldest in the UK, can be seen on the cliffs and the town walls with the original town gate offer a sense of heritage and history which can be further explored in the nearby town museum. With a wealth of attractions, boating on the river and glorious attractions, everyone will find something to enjoy when holidaying in one of the family-friendly holiday cottages in and around Chepstow.

Aerial view of a holiday cottage surrounded by fields beneath a hilltop wood.
Sleeps
2
Bedrooms
1

Orchard Cottage is a gorgeous stone-built romantic holiday cottage in the Wye Valley in a designated National Landscape in Penterry, Monmouthshire. The pet-friendly cottage offers contemporary comforts, a log fire, traditional charm, seclusion, an outdoor fire pit, and lovely rural views across Monmouthshire.

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Two shepherd huts at dusk, converted and linked to form a single unit.
Sleeps
2
Bedrooms
1

Anne’s Hut blends into the surrounding woodland. The unique former shepherd’s hut has been fashioned into a romantic holiday cottage in Penterry, Monmouthshire, which boasts extensive gardens with wonderful countryside views, luxurious décor, a wood burner, an outdoor firepit and contemporary comforts.

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Chepstow Castle sits on top of the cliffs on the town’s outskirts overlooking the River Wye and is the oldest surviving stone castle in Britain, dating back to 1067. Special events are held at the castle throughout the year, and visitors can explore the majority of the castle, including the battlements that lead into Martens Tower. At the bottom of the town, in an elegant 18th Century townhouse, is Chepstow’s Museum, which shows the development of Chepstow from what was once an important port and bustling market town. The museum also has workshops and other activities running throughout the year for younger children, making it a worthwhile attraction for the whole family.

Chepstow’s location makes it the perfect base to explore the beautiful surrounding area of Wales, with many trails and public footpaths that start and finish in the town. The Wye Valley Walk is the most popular walking route at Chepstow and starts opposite Chepstow Castle, following the beautiful river valley to Rhayader in Powys. The Wye Valley area offers some breathtaking scenery and is a recognised Area of Outstanding Natural Beauty. If you’re interested in something a bit different altogether, Chepstow Racecourse sits at the foot of the Wye Valley and is one of the most popular tracks in the UK. The racecourse offers a friendly atmosphere, and children are admitted free of charge, ideal for a family day out.

Chepstow boasts many pubs and restaurants, so if you want a break from cooking in your cottage, take the family into town for dinner one evening. If you feel like cooking something yourself, Chepstow organises both a Farmers’ Market and a Country Produce Market that happens regularly throughout each month and offers the best and freshest local produce around.

A 20-minute drive from Chepstow takes you to the large Welsh city of Newport. Discover the city’s rich history at the various museums and heritage sites, or enjoy a spot of shopping in Newport’s city centre. The abundance of ancient castles, attractions, restaurants and stunning walks make the town of Chepstow an ideal destination for a family-friendly cottage holiday.

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