
Holiday rentals in Chepstow
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Top-rated holiday rentals in Chepstow
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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 Garden Cottage Sedbury NP167EY
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 .

Romantic Somerset hideaway
Hello! We are Rob and Kate and we have poured our heart and soul into our guest house. Tucked away on the outskirts of sleepy Lympsham, enjoy the countryside around you whilst resting your legs after walking the renowned mendips. Enjoy a glass of wine whilst watching the many birds in the surrounding trees or be a little more adventurous with the numerous local cycle routes. We look forward to meeting you on your stay. Shared driveway next to main house. Not suitable for children or pets.

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.

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.

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.

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 40 Acres of Private Countryside in AONB
Nestled in rolling hills with 40 acres of private tracks, fields, streams, woodland and ancient lime kilns to explore, this rural hideaway is popular with walkers, cyclists and those just wishing to escape the mass media or hustle and bustle of everyday life. Recharge your batteries and enjoy the great outdoors as you toast some marshmallows over the fire pit, say hello to the pet sheep and soak up the sights and sounds of birds, wildlife and sunsets in this peaceful relaxing retreat.

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.
Popular amenities for Chepstow holiday rentals
Other great holiday rentals in Chepstow

Castle House Apartment 2 Georgian town house

Skylark Barn

Wallhope Retreat, Chepstow, Wye Valley

Delightful 3-Bedroom cottage with log burner

Stone Cottage with a splendid Wye Valley View

Spacious Chepstow home with private garden & patio

The Potting Shed at Mathern Palace

Sophisticated Spacious Rural Retreat | Wood Burner
When is the best time to visit Chepstow?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £92 | £94 | £96 | £98 | £100 | £102 | £109 | £110 | £109 | £102 | £99 | £108 |
| Avg. temp | 4°C | 5°C | 7°C | 9°C | 12°C | 15°C | 17°C | 17°C | 14°C | 11°C | 7°C | 5°C |
Frequently Asked Questions
Are there family-friendly vacation rentals in Chepstow?
Chepstow has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Chepstow?
Experience the best of Chepstow with our house rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Where should I stay in Chepstow?
Make yourself at home in Chepstow by choosing from our most frequently booked neighborhoods. We have over 70 vacation rentals in Chepstow, and over 70 vacation rentals in Pwllmeyric.
Do house rentals in Chepstow have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Chepstow. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Chepstow have wifi?
Absolutely! We offer over 10 house rentals with wifi in Chepstow. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Chepstow have free parking?
Absolutely! We offer over 10 house rentals with free parking in Chepstow. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Chepstow

Total holiday rentals
Explore 30 holiday rentals in Chepstow

Nightly prices starting at
Chepstow holiday rentals start at £15 per night before taxes and fees

Verified guest reviews
Over 2,790 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Wifi availability
30 of Chepstow holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chepstow rentals

4.9 Average rating
Chepstow stays are highly rated by guests – averaging 4.9 out of 5!
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- Cotswolds AONB
- Principality Stadium
- Cardiff Castle
- Bannau Brycheiniog National Park
- Stonehenge
- Cheltenham Racecourse
- Wye Valley Area of Outstanding Natural Beauty (AONB)
- Lower Mill Estate
- Bike Park Wales
- Roath Park
- Cardiff Bay
- Zip World Tower
- Sudeley Castle
- Bath Abbey
- Bute Park
- No. 1 Royal Crescent
- Newton Beach - Porthcawl
- Puzzlewood
- Royal Porthcawl Golf Club
- Dunster Castle
- Caerphilly Castle
- Hereford Cathedral
- Bowood House and Gardens
- National Showcaves Centre for Wales




