Vacation rentals in Chepstow

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.

Luxury-BedView/Shower/LBurner/Stars/Dog/WiFi

Our hand built bespoke huts offer a luxurious and spacious living space to relax. Quality fixtures and fittings feature throughout. Located in beautiful countryside, stunning views and its amazing wildlife can be appreciated in the daytime and star gazing at night. An internal bathroom with double size power shower will ensure a luxurious experience. Its character wood stove will keep you cosy all year round. Luxury items: Handmade kitchen, Dab/Bluetooth radio, DVD / TV and Nespresso machine.

5*Barn located between Bath and Bristol - Hot tub

The Little Barn has been transformed into a charming bolt hole, with stylish interiors. Hidden away down a country lane nestled between the world heritage city of Bath and the historic maritime and vibrant city of Bristol, you are spoilt for choice for things to do. Located within a securely gated private driveway in countryside surroundings with an al-fresco patio and private hot tub. This Self catered hideaway is steps away from the Bristol to Bath cycle path and beautiful walking routes

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.

Set in AONB & 40 Acres of Private Countryside

Perfectly situated to explore all the Wye Valley and Forest of Dean has to offer, The Apple Loft is an idyllic getaway popular with honeymooners, walkers, cyclists and those just wishing to escape the hustle and bustle of everyday life. With panoramic views across Mork Valley, guests can walk our grassy tracks, explore the old lime kilns, picnic in our fields, say ‘hello’ to the pet sheep and enjoy the sights and sounds of nature, stars and sunsets in this magical and relaxing retreat.

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.