Chepstow on the River Wye in the South East corner of Wales borders 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 cottages in and around Chepstow.

2 cottages found 2 match all criteria.

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

Orchard Cottage is a gorgeous stone-built romantic cottage in an Area of Outstanding Natural Beauty in Penterry, Monmouthshire. The pet-friendly cottage offers wonderful Wye Valley views as well as contemporary comforts combined with a log fire, traditional charm, seclusion and an outdoor fire pit.

Chepstow Castle sits on top of the cliffs on the town’s outskirts and overlooks the River Wye, and is the oldest surviving stone castle in Britain dating back to 1067. There are special events held at the castle throughout the year, and visitors are able to 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 town house is Chepstow’s Museum, which shows the development of Chepstow from what was once a major port and bustling market town. The museum also has workshops and others activities than run throughout the year for younger children, making it a worthwhile attraction for the whole family.

Chepstow’s location makes it the perfect base from which to explore the beautiful surrounding area of Wales, with a vast amount of 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 breath-taking 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 a huge number of 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 Country Produce Market that happen regularly throughout each month and offer the best and freshest local produce around.

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