
House holiday rentals in Chepstow
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Top-rated house rentals in Chepstow
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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.

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.

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.

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.

Hulbert’s Place: C15th house in the heart of Wells
This charming Grade II-listed two bedroom maisonette is situated within a row of ancient dwellings, just a short stroll from Wells Cathedral, The Bishop's Palace and the heart of Wells. Each of the two levels are embellished with wonderful authentic details such as original beams, restored timber floorboards and stone fireplaces. Originally built in the 15th century, the house has been sympathetically restored with an abundance of character, comfort and style.

Surrounded by woodland 10mins from Bristol Airport
Woodside - 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 addition to our home 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.

Idyllic Historic Cottage
This charming character grade II listed cottage, built in the 1600's is set the middle of the beautiful village of Lower South Wraxhall. Ideally positioned just five minutes from the historic town of Bradford on Avon, twenty minutes from the UNESCO city of Bath and sitting within the Cotswolds. Nestled in an exquisite cottage garden, the property is fully equipped for summer garden bbq's or cosy winter evenings by the fire.
Popular amenities for house rentals in Chepstow
House rentals with a pool

Maple cottage

40% off June Weekends. Private Heated Pool.

Modern inner city 3 bed eco house

Boundary Court Barn, Selsley common, Stroud

Cotswolds Cottage, Heated Pool, Tithe Barn Views

The Moretons Farmhouse

Barn - heated swimming pool, hot tub & log burner

Beach House
Weekly house rentals

Stunning 17th century Cotswolds townhouse annexe

Delightful 3-Bedroom cottage with log burner

Forest Cottage

The Pink 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

Cider Mill Monmouthshire.Views of Black Mountains

Trwyn Tal Cottage

Luxury boutique holiday Cottage, 2 bed, 2 bathroom
Private house rentals

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

Modern Chapel Conversion in The Forest of Dean

The Courtyard Barn overlooking Monmouth.

Romantic rural barn nestled in The Mendip Hills

Noxon Pond Cottage

Sumptuous Two Bed Home in Portishead & EV charger

‘Ty Crindau’, 4 BR, Pool room, Sleeps up to 7; 4BR

Country Farmhouse | Hamlet Views & Walks from Door
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





