
House holiday rentals in Chepstow
Find and book unique houses on Airbnb
Quick stats about house rentals in Chepstow

Total holiday rentals
Explore 20 holiday rentals in Chepstow

Nightly prices starting at
Chepstow holiday rentals start at $14 AUD per night before taxes and fees

Verified guest reviews
Over 670 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Wi-Fi availability
20 of Chepstow holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Chepstow rentals

5 Average rating
Chepstow stays are highly rated by guests—averaging 5 out of 5!
Top-rated house rentals in Chepstow
Guests agree: These houses are highly rated for location, cleanliness and more.

The Barn. Perfect for family & friends to meet up.
This very spacious barn conversion is the perfect place to meet family & friends, to relax and “re-connect”. The large fully equipped open plan kitchen and dining room join into the light and comfortable lounge to form the perfect social space plus there's a games room with full size table tennis! Extensive outside patios & gardens provide stunning views over the Severn Vale and wonderful sunsets. Three of the four bedrooms are on the ground floor; all have private en-suites with shower or bath.
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Colliers Cottage at The Barracks, Forest of Dean
Situated in the heart of the Forest of Dean, you will find Colliers Cottage. An ex-colliers cottage that has been extensively renovated in 2024, it comprises 2 bedrooms (1 with en-suite), family bathroom, kitchen, lounge (with sofa bed), dining room and a large, fully fenced private garden with off road parking If you want a stay where you are surrounded by nature, look no further! This is an ideal location for keen walkers, runners and cyclists with off road trails just a short distance away
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Monmouth Georgian owned by our family since 1923
Spacious and charming Georgian home with private garden and parking. Easy 12 min. walk into historic Monmouth town centre with diverse shops, restaurants and supermarkets. Our home has been in our family since 1923 and retains many original features but updated to suit modern comfort and needs. Great access to beautiful surrounding region of Wye Valley and Forest of Dean. Our home boasts a well-appointed kitchen (with AGA), fast internet, sunroom and huge windows that fill the house with light.
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The Sheiling | Countryside Escape with Hot Tub
Countryside home renovated to a high standard in the village of Llanvaches on the edge of Wentwood Forest, the largest ancient forest in Wales. Located between Newport and Chepstow, The Sheiling has views over the open countryside and is perfect for a relaxing getaway offering peaceful forest walks, scenic views, and exploring the exceptional beauty and attractions of the surrounding area. Our local pub/restaurant is a short walk down the lane and there are a variety of traditional pubs nearby.
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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.
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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
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Forest Cottage
There are no hidden extra payments, the nightly fee is total. Self catering cottage, originally built in the 1800's, restored and extended to provide a high standard of accommodation. Set in private gardens which extend to 23 acres and with outstanding views across the Usk valley. The garden area provides 2 large decked viewpoints, Private parking. The property has retained its original stone spiral staircase which might prove difficult for guests with mobility issues or the very young.
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Cider Mill Monmouthshire.Views of Black Mountains
Beautiful converted Cidermill set in the Wye Valley, with stunning views of the Black Mountains, quiet rural location three miles from the historic town of Monmouth, therefore we are not suitable for party people. Also not far from The Forest of Dean and the mountain bike tracks, Ideally situated for country walks, comes with ample parking space for two or three cars. Short drive to several country inns and restaurants. What three words compound.quantity.roadways will bring you direct.
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Entire House . Self Catering . Almondsbury
Roylands Farm Cottage is located on a working farm, surrounded by countryside yet easy access to motorway networks. Ideally located for exploring Bristol and surrounding areas. The property allows sole use of entire house. The property has 5 bedrooms, four with en-suites, a family bathroom, a lounge with conservatory, Kitchen dinner with all cooking facilities available. A large private garden, with outdoor seating, BBQ and pizza oven for you to enjoy. Ample off road parking.
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Cosy cottage in village centre.
Newly renovated and restored to a very high standard, the cottage has retained its traditional features.It is warm and cosy located in the centre of the popular village of Aylburton. Enclosed rear terrace and secure bike storage. The fitted kitchen is fully equipped with everything you need to prepare meals, having said that, there's a great pub next door. There is also a BBQ and outdoor seating, just a step up from the kitchen to enjoy a morning coffee on the sunny patio.
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Caithness Holiday Home
Caithness is a beautiful, spacious and comfortable 6 bedroomed holiday home - perfect for large families - situated on the banks of the Monmouthshire Brecon Canal. It is a home from home, run by a small family business. Originally built in 1959, it has recently been extended and renovated into a contemporary holiday home which sleeps up to 10. It boasts beautiful views and is the perfect destination to enjoy a relaxing escape to the Welsh countryside.
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Delightful 3-Bedroom cottage with log burner
1 Park View is a recently renovated 19th century cottage, located in the peaceful Gloucestershire village of Tutshill. The town of Chepstow is only a 10 minute walk away crossing over the Welsh border via the old Wye Bridge (1816). It's a great location if you're looking for a break in the countryside with plenty to explore in the Forest of Dean as well as the beautiful Wye Valley (AONB) and only a 5 minute walk from the Offa's Dyke national trail.
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Popular amenities for Chepstow house rentals
House rentals with a pool

Modern inner city 3 bed eco house
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Boundary Court Barn, Selsley common, Stroud
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The Warm Hearth: 18th century barn retreat.
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Green Hat Stays - Chepstow - Harvax House
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The Old Rectory with Swimming Pool
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Luxury Countryside House | Spacious & Picturesque
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Buckstone House Coach House
LocationFamilyIndoor spaces

Pwll Court Retreat, Swim Spa, sleeps 12 people
LocationFamilyBreakfast
Weekly house rentals

Donkey Shed
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Stunning Views, Hot Tub, Pizza Oven & Fire Pit
ValueFamilyParking

Lilac Cottage
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Oakwood Cottage, Cannop in heart of Forest of Dean
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Luxury In Langstone!
LocationFamilyCheck-in

Pet friendly 3 Bed home ideal for families, groups
LocationFamilyAccuracy

Modern open plan home, stunning panoramic views
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Cotswolds Romantic Getaway in Luxury Barn
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Private house rentals

Stylish barn in The Forest of Dean
LocationFamilyAccess

Gardener's Cottage, part of a 16th century manor.
ValueFamilyEV charging

Beautiful Barn near Bristol in Picturesque Setting
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A most unusual Manor House
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The Pink Cottage
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Country Farmhouse | Hamlet Views & Walks from Door
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20fairview Chepstow
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New 3 Bedroom Flat Close to Station
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Destinations to explore
- Longleat Safari Park
- Cotswolds AONB
- Stonehenge
- Brean Beach
- Lower Mill Estate
- Bike Park Wales
- Cheltenham Racecourse
- Wye Valley Area of Outstanding Natural Beauty (AONB)
- Cardiff Bay
- Cardiff Castle
- Roath Park
- Cotswold Wildlife Park
- Puzzlewood
- Bath Abbey
- Barry Island Beach
- Sudeley Castle
- Zip World Tower
- No. 1 Royal Crescent
- St Audrie's Bay
- Bute Park
- Waterfall Country
- Principality Stadium
- Newton Beach - Porthcawl
- Ashton Court Estate





