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

Portishead eco-home with a View
The Coach House is a converted coach house and stables. Downstairs, it has a 42 square metre open-plan living space, with a well-equipped kitchen, dining and living area. There is even a small pool table. Upstairs, bedroom 1 has a double bed and views of Severn Estuary towards Wales. Bedroom two also has a double bed doubling as an office with a large oak table. The bathroom has a shower and bath. The walls are decorated with our art work including many of local places you may like to visit.

BEAUTIFUL Tiny House: Whitsun Lodge
Tiny little lodge/House in Bristol. Detached from our house with access to the garden. 10 minutes drive from THE WAVE. 30 seconds walk from Aerospace Bristol (Concorde museum) Great links to the City Centre Comprising of full kitchen, En-suite bathroom and shower, comfy double bed (premium mattress) Smart TV already connected to Netflix/NowTV/Disney+ Use of the washing machine if you need Me, My wife Charlee, My baby son Finley and our little Dog Louie look forward to welcoming you 😄

Birch Cottage
Set in the Countryside just outside the market town of Thornbury, Birch cottage is moments away from Bristol, Wales and 30 mins to the Cotswolds. Standing in its own private garden with stunning views across the river Severn into Wales, friendly sheep are your neighbours. The Cottage is brand new, fitted to a high standard with its own kitchen, en suite and private gated parking 10 mins from the M4/5. Close by are:The Wave, Clifton Bridge, Wye Valley, Bristol docks and Thornbury Castle.

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

Elegant Family-Friendly Retreat Stunning Views
Beautiful Family & Friends Retreat in the Wye Valley & Forest of Dean Looking for the perfect getaway for your family and friends. This stylish and spacious barn conversion offers everything you need for a memorable stay, with breathtaking views, incredible outdoor adventures, and plenty of on-site activities for all ages. River kayaking, wild swimming, fishing, horse riding, golf, zip wire & inland surfing. You'll love meeting our friendly chickens( & enjoy fresh eggs during your stay!

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.

Stunning, stone property with city views
Immaculately presented two bedroom property located moments from the bustling city streets. This stunning property has the most beautiful views from the terrace, overlooking the UNESCO city of Bath, large living and dining spaces, two bedrooms both with ensuite bathrooms and off street parking. A real gem in the tranquility of elegant Widcombe with an abundance of local cafes, shops, pubs and restaurants only a short stroll away. Come, refresh and relax!

Beautiful Studio 1mile to Marina /Lake Grounds
This fully furnished, renovated space - studio apartment is nestled in a cul-de-sac developed by the renowned Free Mantle. It offers a bright open plan living space, kitchenette with appliances. En-suite finished to the highest standards with amenities. Enjoy watching Netflix, YouTube and general stations on an impressive 65 inch smart TV. Super fast broadband. If you need any assistance during your stay your hosts are right next door and happy to help.

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.

Cottage luxe in The Cotwolds
Wycke Cottage welcomes you with unequivocal charm and a little luxe at every turn. Hunker down in style in the picture-perfect Cotswold setting in the heart of Painswick. This 400-year-old cosy cottage, sits opposite the historic church. With stunning sunset views across to the church's beautiful spire and clockface, and its much storied 99 cloud-like yew trees, this stay offers the quintessential Cotswold experience.

Fuchsia Barn, romantic Cotswolds
Fuchsia Barn is a brand new purpose built Airbnb unit, finished to a very high standard, with lots of natural materials giving it a relaxing and cosy atmosphere. It is situated 12 minutes walk from the beautiful village of Castle Combe, often voted the prettiest in the country, and featured in many films. There are wonderful woodland walks from the property, and two village pubs within walking distance

Forest Cottage
Self catering cottage, originally built in the 1800's, restored and extended to provide a high standard of accommodation. Set in private gardens with outstanding views across the Usk valley. The garden area provides 2 large decked viewpoints, Private parking. The property has retained it's original stone spiral staircase which might prove difficult for guests with mobility issues or the very young.
Popular amenities for house rentals in Chepstow
House rentals with a pool

Olli's Summer House - Jacuzzi & Natural pool

Maple cottage

Granary Cottage with access to indoor pool & spa

The Old Rectory with Swimming Pool

Dog friendly with hot tub and Pool -The Pool House

Modern inner city 3 bed eco house

Boundary Court Barn, Selsley common, Stroud

Cotswold Farmhouse with Swimming Pool
Weekly house rentals

Stunning 17th century Cotswolds townhouse annexe

Delightful 3-Bedroom cottage with log burner

Rectory Cottage - Luxury Gloucestershire Retreat

The Pink Cottage

Charming Retreat in the Heart of Wye Valley AONB

Gardener's Cottage at Mathern Palace

Stunning Views, Hot Tub, Pizza Oven & Fire Pit

Great Links to M4, Chepstow, Bristol, Cardiff
Private house rentals

The Beehive - self catering in the heart of the Forest of Dean

Ben Y Byd

The Courtyard Barn overlooking Monmouth.

Severn View Barn. A country hideout next to our cottage. Stylishly furnished in a rustic luxury home theme. comfortable & cosy! -5 minutes from M5, Junction 14

The Lodge

The Snug Luxury Cottage Retreat.

Spacious Rustic House in Wye Valley | Wood Burner

Sophisticated Spacious Rural Retreat | Wood Burner
Quick stats about house rentals in Chepstow

Total holiday rentals
Explore 10 holiday rentals in Chepstow

Nightly prices starting at
Chepstow holiday rentals start at $25 SGD per night before taxes and fees

Verified guest reviews
Over 570 verified reviews to help you choose

Wifi availability
10 of Chepstow holiday rentals include wifi access

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

5 Average rating
Chepstow stays are highly rated by guests – averaging 5 out of 5!
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- 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
- Puzzlewood
- Dunster Castle
- Caerphilly Castle
- Bowood House and Gardens
- Hereford Cathedral
- Dyrham Park




