
House holiday rentals in Chepstow
Find and book unique houses on Airbnb
Top-rated house rentals in Chepstow
Guests agree: these houses are highly rated for location, cleanliness and more.

Unique Private Slad Valley Contemporary Chic Barn
Peglars Barn was completed in 2019, the entire front of this barn is glass which brings the stunning Slad Valley to you at all times, with nothing except the odd animal to distract you from your back to nature experience. This property has everything, blinds, super kingsize bed, en-suite walkin shower, laundry & loo, fully equiped kitchen, huge Smart TV, DVD, WiFi, Bose speaker, Nespresso machine, Laurie Lee trail walking map & other trails. Please read on for more local interest for your stay.

Tregaron Cottage, Upper Cwmbran
Nestled in the tranquil foothills of Blaen Bran Community Woodlands. A perfect, cosy getaway for couples, families & pets (plz NB there is an additional charge for pets) The cottage boasts exceptional mountain views. Perfectly situated for walkers & cyclists to explore the nearby trails inc BikePark Wales trail. 30 sec walk to The Bush Inn Pub, 3 min walk to The Queen Inn (recently reported as the worlds 1st vegan steakhouse), both friendly & welcoming, serving excellent meals & craft beers.

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.

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.

Grist Mill - listed Cotswold mill at Owlpen (1728)
The Grist Mill is an early 18th-century watermill which sleeps up to 8 in four double bedrooms. This listed Grade 2 landmark building has been restored as a gem of a holiday home, with contemporary comfort and style, surmounted by lantern and cupola. Enjoy open plan living in traditional style on the ground floor, and as you head up through the house you'll find cosy bedrooms and old machinery still in place, a relic of times past. Wooden beams, comfortable beds and new bathrooms.

Quiet Edwardian era House, Painswick
Welcome to our family owned Edwardian era house situated in Painswick. Renovated with hosting in mind, we'll have everything you need for a relaxing stay. Situated just off the Cotswold Way national trail, it's the perfect pit-stop for keen walkers (or runners!). If sight seeing is more your thing, the popular 18th Century Rococo Garden is just a 5 minute walk away. Ideally located for travel to Stroud, Cheltenham, Cirencester and Gloucester all within a 20 min drive.

Beautiful Cotswold Stone Cottage
Situated close to the Cotswold Way and the Gloucestershire Way footpaths, Close Cottage (the earliest building in Coberley circa 1550) really is in the heart of the Cotswold Hills. The self contained property comprises: two double bedrooms, fully equipped kitchen, shower room and a cosy lounge with wood burner. The traditional Cotswold stone cottage overlooks picturesque countryside and is situated within ten minutes drive from the beautiful and popular spa town of Cheltenham.

Self catering cottage, sleeps 4, in Portishead.
The early 18C cottage is a part of our home but totally self contained. It retains many of the features of the time and is full of character. The two doubles are a good size and have wardrobes and shelving. Both have tea and coffee making facilities. The property enjoys two bathrooms; each close to the each of the bedrooms. There is a large lounge with a wood burning stove, ample seating, TV/DVD player and a piano. The large kitchen has a range, microwave cooker and dishwasher.

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

Olli's Summer House - Jacuzzi & Natural pool

The Old Rectory with Swimming Pool

Granary Cottage with access to indoor pool & spa

Dog friendly with hot tub and Pool -The Pool House

Modern inner city 3 bed eco house

Boundary Court Barn, Selsley common, Stroud

Cotswold Farmhouse with Swimming Pool

Luxury Cosy Cottage with Garden
Weekly house rentals

The Old Bakery - 11B

Delightful 3-Bedroom cottage with log burner

Redland Suites: The Mews. Great Location & Sleep 4

Unique Cosy Retreat - Spacious 3-Bed Farm House

The Pink Cottage

Sumptuous Two Bed Home in Portishead & EV charger

Gardener's Cottage at Mathern Palace

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
Private house rentals

Lovely Spacious 2 bed/Scenic location, Parking

41 The Green House, Usk

Wharfinger's Cottage

Long Stays-4bed house-Parking-By FabAccommodation

Newport 3-Bedroom Home with Pool & Table Tennis

Charming Country Cottage | Peaceful Nature

Sophisticated Spacious Rural Retreat | Wood Burner

Tythe Barn @avonfarmcottages
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
- Durham Holiday rentals
- Paris Holiday rentals
- London Holiday rentals
- Picardie Holiday rentals
- Grand Paris Holiday rentals
- Thames River Holiday rentals
- South West Holiday rentals
- Inner London Holiday rentals
- Rivière Holiday rentals
- Dublin Holiday rentals
- South London Holiday rentals
- Central London Holiday rentals
- Cotswolds AONB
- Principality Stadium
- Cardiff Castle
- Bannau Brycheiniog National Park
- Stonehenge
- Cheltenham Racecourse
- Wye Valley Area of Outstanding Natural Beauty (AONB)
- Lower Mill Estate
- Bike Park Wales
- Roath Park
- Cardiff Bay
- Zip World Tower
- Sudeley Castle
- Bath Abbey
- Bute Park
- No. 1 Royal Crescent
- Newton Beach - Porthcawl
- Puzzlewood
- Royal Porthcawl Golf Club
- Dunster Castle
- Caerphilly Castle
- Hereford Cathedral
- Bowood House and Gardens
- Dyrham Park




