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

Total vacation rentals
Explore 20 vacation rentals in Chepstow

Nightly prices starting at
Chepstow vacation rentals start at G$2,092 GYD per night before taxes and fees

Verified guest reviews
Over 670 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Wi-Fi availability
20 of Chepstow vacation rentals include wi-fi 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!
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.
LocationFamilyView
4.99 out of 5 average rating, 210 reviews
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.
LocationFamilyIndoor spaces
4.99 out of 5 average rating, 215 reviews
Offa's Hideaway - Wye Valley
Offa's Hideaway is an idyllic and peaceful retreat on Offa's Dyke footpath in the village of Redbrook. Enjoy the private patio and veranda overlooking the Wye Valley woodlands, with a BBQ and petanque court. Recently renovated to a high standard it includes an open living and kitchen area with Emma Sleep king sofa bed, dual aspect bedroom with king bed, and modern bathroom with large deluxe shower. The space has private parking accessed via a magical woodland path with atmospheric lighting.
FamilyLocationHeating
4.94 out of 5 average rating, 106 reviews
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.
ValueLocationLaundry
5.0 out of 5 average rating, 134 reviews
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
ValueLocationHospitality
4.92 out of 5 average rating, 177 reviews
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.
ValueFamilyCheck-in
4.96 out of 5 average rating, 323 reviews
Cotswolds Romantic Getaway in Luxury Barn
The Barn at Church View is a unique luxury conversion of a 200 year old stone former calving barn on the western fringe of The Cotswolds, near the maket towns of Thornbury and Wotton-under-Edge. Its privileged countryside location is within easy reach of the vibrant cities of Bristol, Bath and Gloucester offering an abundance of things to do. The recently renovated barn is a tranquil private space away from noisy roads, the perfect setting for your next holiday or romantic getaway.
LocationValueComfort
4.95 out of 5 average rating, 224 reviews
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.
FamilyLocationBackyard
4.97 out of 5 average rating, 121 reviews
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.
FamilyLocationSleep quality
4.96 out of 5 average rating, 176 reviews
Redland Suites: The Mews. Great Location & Sleep 4
This beautiful 2-bedroom high spec mews house sleeps 4 guests comfortably. A gorgeous open plan fully equipped kitchen and living area, two bedrooms with king sized beds, both have luxury en-suite bathrooms one with a waterfall shower and the other with a bath. The property also has a downstairs toilet and utility room. These are just some of the features to make your stay perfect. The high-end finish and furniture has been selected with your comfort in mind.
FamilyLocationDecor
4.94 out of 5 average rating, 107 reviews
Bath Stone Retreat | City Views + Free Parking
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!
LocationFamilyRiver
4.98 out of 5 average rating, 117 reviews
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.
FamilyLocationLong stay
4.93 out of 5 average rating, 101 reviewsPopular amenities for Chepstow house rentals
House rentals with a pool

Large Georgian House with Indoor Swimming Pool
FamilyLocationHeating
4.86 out of 5 average rating, 118 reviews
Boundary Court Barn, Selsley common, Stroud
LocationValueBreakfast
4.97 out of 5 average rating, 152 reviews
Modern inner city 3 bed eco house
FamilyValueParks
4.9 out of 5 average rating, 544 reviews
The Warm Hearth: 18th century barn retreat.
ValueFamilyHeating
4.87 out of 5 average rating, 147 reviews
Green Hat Stays - Chepstow - Harvax House
LocationFamilyAccuracy
5.0 out of 5 average rating, 3 reviews
The Old Rectory with Swimming Pool
LocationValueGetting around
4.83 out of 5 average rating, 40 reviews
Luxury Countryside House | Spacious & Picturesque
FamilyLocationWifi
4.64 out of 5 average rating, 11 reviews
Charmandene: 5-Bedroom Villa with Pool & Large Sec
FamilyLocationAccuracy
4.88 out of 5 average rating, 34 reviewsWeekly house rentals

Birch Cottage
LocationFamilyGrill
4.98 out of 5 average rating, 323 reviews
Donkey Shed
FamilyValueLayout
5.0 out of 5 average rating, 208 reviews
Colliers Cottage at The Barracks, Forest of Dean
LocationValueAccess
4.99 out of 5 average rating, 143 reviews
Stunning Views, Hot Tub, Pizza Oven & Fire Pit
ValueLocationIndoor spaces
4.97 out of 5 average rating, 116 reviews
Woodwells - Cotswold stone house in ancient woods
LocationFamilyComfort
4.9 out of 5 average rating, 115 reviews
Monmouth Georgian owned by our family since 1923
ValueLocationNearby
4.91 out of 5 average rating, 138 reviews
Lilac Cottage
FamilyValueWifi
4.94 out of 5 average rating, 261 reviews
Gardener's Cottage, part of a 16th century manor.
ValueLocationCheck-in
4.96 out of 5 average rating, 353 reviewsPrivate house rentals

The Loft House - Beautiful House in Best Location
ValueLocationAccess
4.98 out of 5 average rating, 335 reviews
Cosy Private Studio. Fast Wi-Fi & Parking.
LocationValueLong stay
4.91 out of 5 average rating, 105 reviews
A most unusual Manor House
FamilyLocationRiver
5.0 out of 5 average rating, 42 reviews
The Pink Cottage
LocationFamilyParking
4.88 out of 5 average rating, 86 reviews
Country Farmhouse | Hamlet Views & Walks from Door
FamilyLocationLayout
4.97 out of 5 average rating, 33 reviews
20fairview Chepstow
FamilyValueKitchen
4.82 out of 5 average rating, 22 reviews
New 3 Bedroom Flat Close to Station
LocationFamilyCondition
5.0 out of 5 average rating, 8 reviews
Wye Valley Retreat | Deer Garden & River Views
LocationFamilyHospitality
4.88 out of 5 average rating, 41 reviewsDestinations 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





