Holiday 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.

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.

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

3 bedroom, peaceful, secluded, & large garden

Hidden away on the edge of the ancient Forest of Dean, in the beautiful Wye Valley, with a large secluded garden, accessed by a mile long, narrow, single track lane, hanging with ferns in summer. It's is a fabulous place for walkers and town escapees. Once a woodman’s cottage, with a cosy, spacious interior, fully equipped kitchen, log burner, very comfortable beds, all you need for a relaxing break. Not suitable for young children 1-12, the large garden has a pond and steep terracing.

Birch Cottage with woodland sauna

Birch Cottage is a charming 3-bedroom stone cottage with a secluded woodland sauna cabin and views across the Wye Valley countryside. It is located on Offas Dyke footpath on a very quiet road, so is great for anyone looking to explore the network of Wye Valley footpaths. Monmouth, Forest of Dean, Bristol, Bath and Cardiff are close enough for day visits. Whatever season you prefer, it's a wonderful place to recharge your batteries and connect with nature.

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.

Luxurious homely and cosy 1st floor apartment.

The Folly is on the first floor and is part of a contemporary country house set in four acres of gardens and paddocks. It is fully furnished to a high standard and very private. Open plan with dual aspect, lovely views to front and rear with balcony and seating overlooking the garden. King size and single bedrooms with immaculate shower room. Perfect rural location to escape to the country to re-charge and relax.

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!