
Holiday rentals in Chepstow
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Chepstow
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

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.

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 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.

The Dairy - Quaint village stay
The Dairy is a quaint self-contained annex at the side of our detached property in the picturesque village of Tockington just north of Bristol. There is a bedroom on a mezzanine over an open plan living/dining/kitchen area and shower room. The accommodation is situation on the approach to the village, accessed from a private driveway with parking at the front. You have the use of a private veranda with views of the countryside and the opportunity to take in the village atmosphere.

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.

Adjoined Stone Cottage Wye Valley (Five Springs)
Self-catering cottage in a small quiet Wye Valley village in in the hills above Monmouth. Set in 6 acres of woodland and hidden gardens. Large bedroom with comfortable king (60") & single bed, lounge with log burner, TV & WiFi. Stunning large spa room with sauna, shower, jacuzzi & small toilet room. Kitchen with induction hob, grill and fan oven, microwave, washing machine, tumble dryer and fridge freezer, separate bathroom with toilet.

Private Annex with gated parking close to M4.
Modern, light and homely annex on private land with gated parking situated in a lovely little village called Magor. The village shops, restaurants and pubs are a short five minute stroll away and are well worth a visit. Magor has fantastic links being 2 minutes from the M4. We are approx 30 minutes to centre of Bristol and 30 minutes to Cardiff, 20 minutes to centre of Newport and 10 minutes to the Celtic Manor Resort and ICC.
Popular amenities for Chepstow holiday rentals
Other great holiday rentals in Chepstow

Castle House Apartment 2 Georgian town house

Cosy Rural Cabin Hideaway

Delightful 3-Bedroom cottage with log burner

Wallhope Retreat, Chepstow, Wye Valley

Stone Cottage with a splendid Wye Valley View

The Potting Shed

The Lodge

Cute little Wye Valley cottage
When is the best time to visit Chepstow?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £94 | £95 | £97 | £100 | £101 | £103 | £97 | £98 | £100 | £99 | £97 | £96 |
| 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 |
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!
Destinations to explore
- Paris Holiday rentals
- London Holiday rentals
- Picardy Holiday rentals
- Grand Paris Holiday rentals
- Thames River Holiday rentals
- South West England Holiday rentals
- Inner London Holiday rentals
- Rivière Holiday rentals
- Dublin Holiday rentals
- South London Holiday rentals
- Central London Holiday rentals
- Yorkshire Holiday rentals
- Cotswolds AONB
- Principality Stadium
- Brecon Beacons national park
- Stonehenge
- Lower Mill Estate
- Bike Park Wales
- Cardiff Castle
- Cheltenham Racecourse
- Roath Park
- Newton Beach Car Park
- Sudeley Castle
- Bath Abbey
- Royal Porthcawl Golf Club
- No. 1 Royal Crescent
- Zip World Tower
- Bute Park
- Puzzlewood
- Dunster Castle
- Caerphilly Castle
- Bowood House and Gardens
- National Showcaves Centre for Wales
- Porthcawl Rest Bay Beach
- Llantwit Major Beach
- Hereford Cathedral