
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.

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.

Individual, detached Annexe…
This individual Annexe is situated near the wonderful market town of Coleford in the heart of the Forest of Dean, which has all the amenities needed to make your stay enjoyable and is an ideal base to explore the area. There are many places to visit, such as, Puzzlewood, (walking distance), Clearwell caves, Symonds Yat and the Wye Valley. There is a footpath that leads directly from the property into the forest so you can enjoy walking and biking. There’s also two 18 hole golf courses nearby.

BEAUTIFUL Tiny House: Whitsun Lodge
Tiny little lodge/House in Bristol. Detached from our house with access to the garden. 10 minutes drive from THE WAVE. 30 seconds walk from Aerospace Bristol (Concorde museum) Great links to the City Centre Comprising of full kitchen, En-suite bathroom and shower, comfy double bed (premium mattress) Smart TV already connected to Netflix/NowTV/Disney+ Use of the washing machine if you need Me, My wife Charlee, My baby son Finley and our little Dog Louie look forward to welcoming you 😄

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

Willsbrook Lodge
This little piece of heaven sits in the centre of the village of Raglan, within the grounds of Willsbrook House, just moments from its castle & within walking distance of a pub, restaurant, village Supermarket (Tesco 7am-11pm) & award winning butcher. Ideally located for exploring Tintern Abbey, floral Usk, Abergavenny and Monmouth (all under 10 miles) visitors can also enjoy golf courses abound and the Breacon Beacons, Offa's Dyke, Wye and Usk Valleys which all provide good walking.

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.

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.

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.

Cottage luxe in The Cotwolds
Wycke Cottage welcomes you with unequivocal charm and a little luxe at every turn. Hunker down in style in the picture-perfect Cotswold setting in the heart of Painswick. This 400-year-old cosy cottage, sits opposite the historic church. With stunning sunset views across to the church's beautiful spire and clockface, and its much storied 99 cloud-like yew trees, this stay offers the quintessential Cotswold experience.

Delightful Cottage Retreat
Nestled in the heart of the idyllic village of Lower South Wraxhall, this beautiful country cottage is the perfect place to get away from it all. Just north of the historic town of Bradford on Avon, 20 minutes to Bath and sitting within the Cotswolds, the cottage is well placed for exploring. Beautifully decorated and well equipped for blissful summer days or cosy winter evenings you are guaranteed to have a special stay.
Popular amenities for Chepstow house rentals
House rentals with a pool

Olli's Summer House - Jacuzzi & Natural Pool

Granary Cottage with access to indoor pool & spa

The Old Rectory with Swimming Pool

Dog friendly with hot tub and Pool -The Pool House

Modern inner city 3 bed eco house

Boundary Court Barn, Selsley common, Stroud

The Locks

Country House, heated pool, hot tub & great views!
Weekly house rentals

2 Bedroom Family Home in Chepstow with Parking

Delightful 3-Bedroom cottage with log burner

Rectory Cottage - Luxury Gloucestershire Retreat

The Pink Cottage

Charming Retreat in the Heart of Wye Valley AONB

Ty Gwilym; a beautiful Brecons barn conversion

Designer house, balcony, views, sauna, pool

Portishead eco-home with a View
Private house rentals

Birdsong Cottage

Rose Bungalow

Very Spacious 1 Bed Home in the Countryside

Gardener's Cottage

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

Forest Views, Trails & Tranquillity

The Lodge

Cute little Wye Valley cottage
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 $35 NZD per night before taxes and fees

Verified guest reviews
Over 540 verified reviews to help you choose

Wi-Fi availability
10 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!
Destinations to explore
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- Cotswolds AONB
- Principality Stadium
- Brecon Beacons national park
- Stonehenge
- Lower Mill Estate
- Bike Park Wales
- Cheltenham Racecourse
- Cardiff Castle
- Roath Park
- Newton Beach Car Park
- Sudeley Castle
- Bath Abbey
- Royal Porthcawl Golf Club
- Zip World Tower
- No. 1 Royal Crescent
- Bute Park
- Puzzlewood
- Dunster Castle
- Caerphilly Castle
- Bowood House and Gardens
- Hereford Cathedral
- National Showcaves Centre for Wales
- Porthcawl Rest Bay Beach
- Aberavon Beach




