
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.

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

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.

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.

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 off site activities for all ages. River kayaking, wild swimming, fishing, horse riding, golf, zip wire & inland surfing. Nightly rate includes Airbnb fees

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.

Unique Cosy Retreat - Spacious 3-Bed Farm House
Cosy period three bedroom farm house, as part of a Grade II listed building with history dating back to 17th century. Ideal for couples / families. Beautiful walking routes in neighborhood. Cascade House stands in approximately 1.5 acres of mature gardens with extensive parking. The house is located down a 0.2 miles farm lane. We have plenty of secure storage for bicycles. Ample parking available in a gated and secure area.
Popular amenities for house rentals in Chepstow
House rentals with a pool

Orchard House- 6 bed with hot tub & log burner

Olli's Summer House - Jacuzzi & Natural pool

Granary Cottage with access to indoor pool & spa

The Old Rectory with Swimming Pool

Green Hat Stays - Chepstow - Harvax House

Modern inner city 3 bed eco house

Boundary Court Barn, Selsley common, Stroud

Barn - heated swimming pool, hot tub & log burner
Weekly house rentals

Superb Cotswold Honeycomb House

Delightful 3-Bedroom cottage with log burner

The Pink Cottage

Gardener's Cottage at Mathern Palace

Wye Valley Retreat | Deer Garden & River Views

Country Farmhouse | Hamlet Views & Walks from Door

Artist's Retreat - Style, tennis and hot-tub for 4

Beautiful little two bedroom coach house.
Private house rentals

Country retreat with a hot tub and amazing views

The White House

Redland Suites: The Mews. Great Location & Sleep 4

Sedbury Farm Cottage #5

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

Brand new 2 bedroom barn. Stunning views! Hot tub

Redwood House - Free Parking
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
- Cheltenham Racecourse
- Lower Mill Estate
- Wye Valley Area of Outstanding Natural Beauty (AONB)
- Bike Park Wales
- Roath Park
- Cardiff Bay
- Bath Abbey
- Zip World Tower
- Sudeley Castle
- Bute Park
- No. 1 Royal Crescent
- Puzzlewood
- Newton Beach - Porthcawl
- Dunster Castle
- Eastnor Castle
- Caerphilly Castle
- Longleat Safari Park
- Dyrham Park
- Hereford Cathedral




