
House holiday rentals in Chepstow
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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.

Stunning 17th century Cotswolds townhouse annexe
Rounceval House is a marvellous 17th century stone-built town house in the shadow of the south Cotswolds escarpment on the famous Cotswold Way walk. It was an upmarket 11-bedroom boutique hotel until recently. New owners Richard and Leanne now run it as a family home and rent out the self-contained three-double bedroomed eastern annexe wing to guests. It's a lovely space. The bedrooms are exceptionally large. The double beds in them are also very large (either king-sized or super king-sized).

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.

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!

The Game Larders
Wythall is a half-timbered manor house in a secluded and idyllic setting with garden, fresh water lake, wooded grounds and vineyards. You will enjoy peace and quiet here and see an abundance of wildlife. Wine tastings and vineyard tours are also available via appointment. The Game Larders is completely self contained and situated in the west wing of the manor house. It is well equipped and furnished, with access to ample parking space and central heating throughout. Pets are welcome.

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.

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!

Surrounded by woodland 10mins from Bristol Airport
Woodside Lodge - Is an exceptional architect designed barn conversion. Sitting on the entrance to extensive private woodland, whilst located within our own 2 acres of beautiful gardens. We created this stunning Lodge with its large windows, cathedral ceiling and luxurious facilities. Ensuring we had a state of the art home that would take our guests breath away! We could have created two or even three bedrooms from this space but decided less was more.

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.
Popular amenities for house rentals in Chepstow
House rentals with a pool

Olli's Summer House - Jacuzzi & Natural pool

Maple cottage

Private Pool/Cotswold Celebrations /Games Room

Dog friendly with hot tub and Pool -The Pool House

Green Hat Stays - Chepstow - Harvax House

Modern inner city 3 bed eco house

Boundary Court Barn, Selsley common, Stroud

Manor House Farm by Birch Stays
Weekly house rentals

Delightful 3-Bedroom cottage with log burner

The Pink Cottage

Gardener's Cottage at Mathern Palace

Castle Combe Cottage, Cotswolds

Country cottage with scenic views and hot tub

Tregaron Cottage, Upper Cwmbran

Sophisticated Spacious Rural Retreat | Wood Burner

Lilac Cottage
Private house rentals

The Old Bakery - 11B

Cottage in the Cotswolds

Romantic rural barn nestled in The Mendip Hills

Barton Suites- Luxury Home 1 of 2. Sleeps 6

Hill House - Stylish 5 Bed Country House

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 Roundhouse

Hill Coach House
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 £15 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!
Destinations to explore
- Cotswolds AONB
- Principality Stadium
- Cardiff Castle
- Bannau Brycheiniog National Park
- Stonehenge
- Cheltenham Racecourse
- Lower Mill Estate
- Wye Valley Area of Outstanding Natural Beauty (AONB)
- Bike Park Wales
- Roath Park
- Cardiff Bay
- Zip World Tower
- Sudeley Castle
- Bath Abbey
- Bute Park
- No. 1 Royal Crescent
- Puzzlewood
- Newton Beach - Porthcawl
- Dunster Castle
- Royal Porthcawl Golf Club
- Eastnor Castle
- Caerphilly Castle
- Hereford Cathedral
- Dyrham Park




