
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.

Boddington Mill
Boddington Mill is a stunning countryside retreat in the heart of the Cotswolds, steeped in history and rural charm. The building retains industrial mill parts which intersect multiple levels for a unique and generous living space. Its south-facing garden includes outside dining, wood-fired hot tub, and large lawn, home to wildlife and fruit-bearing trees. Inside, the three king sized bedrooms feature luxury bedding beneath vaulted, oak-beamed ceilings and period windows. Sky TV, Sonos speakers.

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.

Breathtaking Cotswolds Restored Chapel Valley View
Step into a rare and remarkable stay at ‘The Old Church’, a lovingly restored & renovated 1820s chapel nestled on the hillside in the idyllic Cotswolds village of Sheepscombe. This enchanting property blends timeless character & period charm with a relaxing contemporary feel. A truly unique picturesque countryside escape. Located in a tranquil woodland setting on the edge of Blackstable Nature Reserve with scenic valley walks, a rustic village setting, a playground & lovely pub down the lane.

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

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.

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.

Unique Cosy Retreat - Spacious 3-Bed Farm House
Escape to a cozy, 17th-century Grade II listed farmhouse steeped in history and charm. Tucked away down a quiet lane, Cascade House is set within 1.5 acres of mature gardens, offering a peaceful sanctuary for couples and families. Explore beautiful walking routes throughout the local area or take advantage of our secure storage for bicycles. With ample gated parking and plenty of space to breathe, this historic retreat is the perfect base for your next countryside adventure.

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.

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.

Elegant Family-Friendly Retreat Stunning Views
Beautiful Family & Friends Retreat in the Wye Valley & Forest of Dean. 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 off site activities for all ages. River kayaking, wild swimming, fishing, horse riding, golf, zip wire & inland surfing. Nightly rate includes 15% Airbnb fee
Popular amenities for house rentals in Chepstow
House rentals with a pool

100 Howells Mere - 100HM - Lakeside Spa Property

40% off June Weekends. Private Heated Pool.

Lakeside | Hot Tub | Pools & Spa | Lower Mill E

Modern inner city 3 bed eco house

Boundary Court Barn, Selsley common, Stroud

Cotswolds Cottage, Heated Pool, Tithe Barn Views

43 Clearwater - Lower Mill Estate + Pools + Spa

Beach House
Weekly house rentals

Wallhope Retreat, Chepstow, Wye Valley

Delightful 3-Bedroom cottage with log burner

The Barn, 2 Bedrooms with Hot Tub, Forest of Dean

Forest Cottage

The Pink Cottage

Cotswold walks & log fires in stylish renovation

Wye Valley Retreat | Deer Garden & River Views

Country Farmhouse | Hamlet Views & Walks from Door
Private house rentals

The West Wing Penthouse Luxury 5 Bedroom Apartment

Spring Cottage - 2 bed countryside retreat nr Bath

The Courtyard Barn overlooking Monmouth.

Romantic rural barn nestled in The Mendip Hills

Sumptuous Two Bed Home in Portishead & EV charger

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

‘Ty Crindau’, 4 BR, Pool room, Sleeps up to 7; 4BR
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 £7 per night before taxes and fees

Verified guest reviews
Over 600 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
- Lower Mill Estate
- Cheltenham Racecourse
- Bike Park Wales
- Wye Valley Area of Outstanding Natural Beauty (AONB)
- Roath Park
- Bath Abbey
- Cardiff Bay
- Zip World Tower
- Sudeley Castle
- Bute Park
- No. 1 Royal Crescent
- Puzzlewood
- Dunster Castle
- Newton Beach - Porthcawl
- St Audrie's Bay
- Eastnor Castle
- National Showcaves Centre for Wales
- Dyrham Park
- Caerphilly Castle





