
Holiday houses 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

Goldcrest-Lodge-Forest-of-Dean
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 delicious 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/wyevalleydairy-uk

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 .

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.

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.

Your own space in colourful Southville!
Hello! Our home is in the vibrant and colourful area of Southville, just a short 15 minute walk from Bristol city centre. Southville is a very popular part of Bristol and home to Upfest, which is Europe’s biggest street art festival. The accommodation itself is a self-contained part of our home with its own private entrance. Inside, you’ll find a bright and spacious bedroom with en suite shower room. Directly beneath in the basement is a lounge area with kitchenette.

Tuckers Lodge
We are situated less than a mile away from the village of St Briavels. We are fairly rural, so what 3 words is a great way to find us, they are: endlessly.balance.drummers Saint Briavels is a vibrant little village in the Forest of Dean, on the edge of the beautiful Wye Valley. It has an inn, a deli, a church and a castle. A monthly farmers' market is held in the village on the first Saturday morning of every month, where you can buy a whole range of local produce.

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.

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

Birch Cottage with woodland sauna

Castle House Apartment 2 Georgian town house

Wallhope Retreat, Chepstow, Wye Valley

Delightful 3-Bedroom cottage with log burner

Dunks Chalet with Hot Tub

Chepstow Apartment–Short Walk to Town&Free Parking

Spacious Chepstow home with private garden & patio

the old Laundry - uk12136
When is the best time to visit Chepstow?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $206 NZD | $209 NZD | $214 NZD | $219 NZD | $223 NZD | $228 NZD | $243 NZD | $246 NZD | $243 NZD | $228 NZD | $221 NZD | $241 NZD |
| 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
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.
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.
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.
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.
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.
What are the most popular amenities for House Rentals in Chepstow?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
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 $33 NZD 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 and kid-friendly amenities

Wi-Fi availability
30 of Chepstow holiday rentals include Wi-Fi 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
- Durham Holiday rentals
- Paris Holiday rentals
- London Holiday rentals
- Picardie Holiday rentals
- Grand Paris Holiday rentals
- Thames River Holiday rentals
- South West Holiday rentals
- Inner London Holiday rentals
- Rivière Holiday rentals
- Dublin Holiday rentals
- South London Holiday rentals
- Central London Holiday rentals
- Cotswolds AONB
- Principality Stadium
- Cardiff Castle
- Bannau Brycheiniog National Park
- Stonehenge
- Wye Valley Area of Outstanding Natural Beauty (AONB)
- Cheltenham Racecourse
- Lower Mill Estate
- Bike Park Wales
- Roath Park
- Cardiff Bay
- Sudeley Castle
- Zip World Tower
- Bath Abbey
- Bute Park
- Newton Beach - Porthcawl
- No. 1 Royal Crescent
- Royal Porthcawl Golf Club
- Dunster Castle
- Puzzlewood
- Caerphilly Castle
- Hereford Cathedral
- Bowood House and Gardens
- National Showcaves Centre for Wales




