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.

The Old Coach House at Tintern, the Wye Valley

The old coach House is a few minutes walk from the centre of Tintern on the banks of the river Wye, where you'll find the famous abbey, as well as places to eat and drink, and shops selling local crafts. The Wye Valley Walk passes the house, and the hourly bus between Chepstow and Monmouth stops just metres away. Staying at the historic Old Coach House in Tintern, you'll experience the unique charm of an early 1800s Welsh cottage, while enjoying modern comforts in a stylish and homely setting.

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.

The Dairy

Take it easy at this unique and tranquil getaway. Set in the Wye Valley, an area of outstanding natural beauty. You can walk/cycle for miles without touching a road. Collect eggs, milk and ice cream from the farm next door Tintern Abbey with its pubs and restaurants is a walk away (an hour); the races, music at the Castle, Clearwell Caves, Puzzlewood, steam train.. and more. Travelling with friends/family? Check our other listing within the same grounds: airbnb.com/h/cosy-wye-valley-getaway

Willow View character cottage in conservation area

Willow View - A period cottage in a lovely conservation area village just north of Bristol. This newly refurbished annexe is perfect for those visiting "The Wave", wanting to cycle on the numerous quiet country roads or simply walk to one of the many excellent village pubs that can be accessed via great countryside walks. 2 minute drive from Old Down Country park, 30 minute drive to Bristol city centre and Forest of Dean. Nearest pub is just across the road plus others within a short walk.

Welsh Gatehouse: Luxury 13th Century Medieval Home

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.

Magical cottage set within a woodland glade

Badgers Bothy is set within a woodland glade in the grounds of the 16th century Amberley Farmhouse and provides the most unique and charming country escape. Our idyllic cottage is set on the edge of Minchinhampton Common (located in an AONB) and with miles of footpaths which are perfect for those wishing to explore the Cotswolds. This beautiful cottage exudes an aura of peace and tranquillity and a haven for those wishing to escape the hustle and bustle of a busy life.

Idyllic Country Retreat in the Forest of Dean

Set in the grounds of a magnificent country home with far reaching stunning views over the River Severn and beyond. This is a perfect place to escape and unwind from the daily hustle and bustle of life. Near to Chepstow and with easy access to the M4 & M5 Motorways and only 2 hours drive from London, 30 minutes from Bristol and 40 minutes from Cheltenham. This cosy studio apartment has only recently been completed to an exceptionally high standard.

The Nursery Wing - Wyndcliffe Court

The Accommodation is just off the Wye Valley walk at Upper Wyndcliff, a spacious and comfortable self-contained first floor flat within a private family house and garden with fabulous views. Guests can explore the beautiful gardens - which they may have seen featured in the May 2022 edition of "The English Garden". There are also wonderful walks and cycle rides from the door to Tintern, Chepstow and the AONB of the Wye Valley.

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.