
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 $17 NZD 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.
4.99 out of 5 average rating, 210 reviews
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
4.99 out of 5 average rating, 142 reviews
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.
4.91 out of 5 average rating, 138 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.
4.99 out of 5 average rating, 215 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.
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
4.91 out of 5 average rating, 176 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.
4.96 out of 5 average rating, 323 reviews
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.
4.95 out of 5 average rating, 293 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.
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.
4.96 out of 5 average rating, 176 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.
4.93 out of 5 average rating, 101 reviews
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.
4.95 out of 5 average rating, 1157 reviewsPopular amenities for Chepstow house rentals
House rentals with a pool

Boundary Court Barn, Selsley common, Stroud
4.97 out of 5 average rating, 151 reviews
Modern inner city 3 bed eco house
4.9 out of 5 average rating, 544 reviews
The Warm Hearth: 18th century barn retreat.
4.87 out of 5 average rating, 147 reviews
Green Hat Stays - Chepstow - Harvax House
5.0 out of 5 average rating, 3 reviews
The Old Rectory with Swimming Pool
4.83 out of 5 average rating, 40 reviews
Luxury Countryside House | Spacious & Picturesque
4.64 out of 5 average rating, 11 reviews
Modern Home with Indoor Swimming Pool & Hottub
4.81 out of 5 average rating, 188 reviews
Pwll Court Retreat, Swim Spa, sleeps 12 people
5.0 out of 5 average rating, 45 reviewsWeekly house rentals

Portishead eco-home with a View
4.97 out of 5 average rating, 172 reviews
Lilac Cottage
4.94 out of 5 average rating, 261 reviews
Cotswolds Romantic Getaway in Luxury Barn
4.95 out of 5 average rating, 223 reviews
Oakwood Cottage, Cannop in heart of Forest of Dean
4.89 out of 5 average rating, 210 reviews
Bath Stone Retreat | City Views + Free Parking
4.98 out of 5 average rating, 117 reviews
Offa's Hideaway - Wye Valley
4.94 out of 5 average rating, 106 reviews
Stunning Views, Hot Tub, Pizza Oven & Fire Pit
4.97 out of 5 average rating, 116 reviews
Forest Views, Trails & Tranquillity
4.9 out of 5 average rating, 108 reviewsPrivate house rentals

Stylish barn in The Forest of Dean
4.92 out of 5 average rating, 348 reviews
Gardener's Cottage, part of a 16th century manor.
4.96 out of 5 average rating, 353 reviews
Caithness Holiday Home
4.99 out of 5 average rating, 217 reviews
Beautiful Barn near Bristol in Picturesque Setting
5.0 out of 5 average rating, 200 reviews
Redland Suites: The Mews. Great Location & Sleep 4
4.94 out of 5 average rating, 107 reviews
The Cart Shed-hot tub, up to 4 bedrooms
5.0 out of 5 average rating, 108 reviews
A most unusual Manor House
5.0 out of 5 average rating, 42 reviews
The Pink Cottage
4.88 out of 5 average rating, 86 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





