Places to stay near Chepstow Racecourse

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

Welsh Gatehouse: Historical Castle with EV Charger

The Welsh Gatehouse: a beautiful historic house with modern amenities - 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, & thick walls keep you cool in summer. Views from the top of the tower are extraordinary: Severn Bridges & Breacon Beacons (‘the terrace’ in our description). Unique, luxurious, quirky, comfortable. Walled enclosed courtyard garden. Dogs welcome (see 'Other Details')

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.

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.

Wye Valley Escape. Romantic Loft on 40-Acre Estate

Romantic luxury loft for two on a 40-acre private estate in the Wye Valley National Landscape. Perfect for honeymooners, stargazers, proposals, anniversaries, or milestone moments. Enjoy panoramic Mork Valley views through the feature arched window, vaulted oak beams, and a cozy fire pit (logs & marshmallows incl.). Includes a generous welcome hamper and exclusive access to our dark skies, meadows, stream, and woodland. A peaceful, magical retreat with high-end, curated experiences available.

Character cottage, stroll to town, Wye Valley base

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

The Vault

The Vault is a really special space, which we hope you can see from the photographs. It is a basement studio apartment with its own private entrance. It is quiet and cosy with underfloor heating and an ambient temperature all year round. This property is very central, making it easy to plan your visit. We are very close to the harbour and the property is on the famous Georgian Square, Queen Square. It feels like you have stepped into a film from Jane Austen as you come out of the building.

Ty Nant Treehouse with covered hot tub

As you enjoy the short buggy ride down to the far end of our woodland you will be astounded when you come across our beautiful woodland cabin set in the treetops. You will immediately feel relaxed as you immerse yourself in the surrounding nature. Lounging chairs on the decking provide the perfect place for your morning coffee listening to the birds sing and soak away your stress in the wood fired hot tub then cosy up in front of the log burner and enjoy the tranquility of the woodland.

Olli's Cottage-Terrace & Jacuzzi

Olli's cottage is situated in one of Bristol picturesque suburds, newly refurbished 700sq Ft/70 Sqm with private terrace and hot tub (£30 extra charge to be settled at the property). In close proximity you have another property called Olli’s Summer house: Swimming pool with waterfall, pool table & ping pong table (£100 extra charge and subject to availability). Located near M4/M5, making travel to/from easy. 3 minutes drive to country pubs.

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.

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!