Family-friendly vacation rentals in Chepstow

Cromwell House, Central Chepstow

Flat 1 is a cosy first floor flat in Cromwell House steeped in history and named after Oliver Cromwell having stayed here when invading the famous Chepstow Castle. We have recently refurbished the property to create a warm and welcoming place to enjoy all that Chepstow and the surrounding areas has to offer. This special place is close to everything and central to Chepstow making it easy to plan your visit. The flat is fully equipped with every thing you would need for your stay along with Wi-Fi

Pineapple Cottage - Chepstow Town Centre (Wales)

17th Century cottage in the heart of Chepstow, close to Offa's Dyke & the Wye Valley. Tucked down a little cobbled street in the town centre, it’s a small but perfectly formed cottage ideal for a couple or a young family. There’s a secret door leading to the second bedroom, where you’ll even get a glimpse of Chepstow Castle from the window. It’s an ideal base for weddings at St Tewdrics (we’ve even hosted the bride and groom!) or for walking and cycling in the Forest of Dean and Wye Valley.

Offas Dyke Cabin

Offas Dyke Cabin is set on a hill surrounded by organic countryside. The views of the Severn Estuary are spectacular, withThe Severn Bridge standing proud amongst it . . We are lucky to be located at the start or finnish of the historic Offas Dyke Path which offers beautiful walks and scenery. The cabin is walking distance to the local village pub which offers a hearty Sunday lunch. Chepstow Town centre with its quirky shops , restaurants and beautiful historical Castle are 5 minutes away .

Chepstow Town. Welsh Cottage.

The house is in the centre of the beautiful old market town of Chepstow. Nestled on the Welsh / English border. We are just a stone's throw from the ancient castle and the impressive Priory Church of St Mary. Within walking distance of the Chepstow Racecourse and a stroll from the railway and bus stations. 300yds from the River Wye and central to all restaurants and cafes etc. Situated near the AONB Wye Valley and Forest of Dean. Please note the property has a Jack & Jill bathroom upstairs.

Cute little Wye Valley cottage

Surrounded by woodland with hilltop views across the Wye Valley to Offa’s dyke, this eco friendly traditional Monmouthshire cottage is the perfect place to unwind and enjoy nature at its very best. Spend time in the garden listening to bird song and the gentle babbling of the stream or step out the gate to explore Cleddon Falls and beautiful view points along the Wye Valley walk. The medieval village of Trellech and Tintern Abbey are also within easy reach off or on road by foot, bike or car.

Spacious cottage, sunny garden, stroll to town

Vauxhall Cottage is a charming home-from-home, ideal for families & friends, yet cosy for couples. The spacious layout offers social areas & quiet nooks, with 4 comfy bedrooms, large kitchen & lounge, sunroom & an enclosed, dog-friendly garden with patio & BBQ. The modernised 1790s Welsh cottage is a short stroll to Chepstow’s historic centre, Castle & riverside, ideal for the racecourse, & to explore the Forest of Dean, Wye Valley & beyond, with easy connections to Cardiff, Bristol & M4/M5.

Peaceful Stone Cottage among fabulous gardens

The Garden House is a peaceful stone cottage set in the historic gardens of High Glanau Manor, the home of H. Avray Tipping (1855-1933) the Architectural Editor of Country Life Magazine from 1907. High Glanau Manor is an important Arts & Crafts house set in 12 acres of gardens designed in 1922. The gardens retain many original features including formal terraces, octagonal pool, glasshouse, pergola and 100 ft long double herbaceous borders. There are spectacular views to the Brecon Beacons

Welsh Gatehouse: Historical Castle with EV Charger

The Welsh Gatehouse is a beautiful historic house with modern amenities. Imagine staying in a fairy tale castle built in 1270. The thick walls, ancient windows & steep spiral staircase say 'history'. Romantic log fires keep you warm you in winter, & the thick walls keep you cool in summer. Views from the top of the tower are extraordinary over the Severn Bridges and the Breacon Beacons (NB we call this the terrace in our description below). Unique, luxurious, quirky yet comfortable.

Lodge farm Woodland dome. Hot tub. luxury escape

A luxurious dome nestled in private woodland and flower garden. An ideal romantic/ family stay near the Cotswolds. Enjoy the wildlife view from your king size bed, woodburning stove, additional heating and air conditioning. Relax on the private decking area, outdoor dining with a barbeque and firepit for toasting marshmallows amongst the trees. The mattresses can be brought down from the loft area for younger children. Rest, relax and reward yourself with the glamping stay with us!

Carpenters Cottage - Central Chepstow with parking

Carpenters Cottage is a quaint cosy one bedroom cottage at the bottom of Chepstow Town. It’s 2 minutes walk to the castle, town centre or the pubs on the river wye. The cottage is fully equipped with all your necessities for a wonderful home from home stay. Recently completely refurbished to a high standard it offers comfort, style and privacy with a 4* luxury finish. We hope you enjoy your stay and want to come again.

Historic cottage opposite Chepstow Castle

Directly opposite the castle, this cottage is in the perfect location for exploring Chepstow and its surrounding areas. The cottage dates back to the 17th century, but has been freshly modernised. Expect a homely yet luxurious stay. Chepstow itself is a historic town, packed with lovely restaurants, pubs, cafés and shops. Our house guide will give you plenty of recommendations to make the most of the area.

Cheerful 3 bedroom cottage a walkers Parìdice!

Gaer Hill cottage is situated just ten minutes from Chepstow race course and 30 minutes walk from the start of wye valley with Tintern abbey 15 mins drive. This 3 bed cottage is the perfect place to explore from or just kick back and relax. If you enjoy farm life this could be the place as you can watch cows graze from the bedroom window or even have sheep pass your front door or maybe a horse wonder by!