
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.

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.

Self catering cottage, sleeps 4, in Portishead.
The early 18C cottage is a part of our home but totally separate and 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. The property enjoys two bathrooms; each close to each of the 2 bedrooms. There is a large lounge with a wood burning stove, ample seating, TV and a piano. The large kitchen has a range, microwave cooker and dishwasher. In the utility room there is a washing and tumble drier.
The Shed at Norbin Barton
Recently built, architect-designed conversion The Shed is perfect for exploring and relaxing. Light, spacious with beautiful decor, the stunning property is set in open countryside with great views. 5 miles from Bath, it's well located for visiting some of the UK's most beautiful places. Quiet and peaceful, birdsong is the only noise you're likely to hear as you unwind. For the active, there is a tennis court outside, many walking and cycling routes and a golf course within 1/2 mile.

Dry Dock Cottage
Relaxing is easy in Dry Dock Cottage: there’s a cinema snug, roll-top bath and king-size bed. The high-tech gadgetry means that, at the touch of a screen, you can control the heating, close the blinds, dim the lights and play your favourite music. With spectacular views from all four levels, this open-plan former dry dock sits at the very water’s edge. Open the bi-fold glass doors from the lounge area, to get even closer to the ducks and the boats that pass by. Pets are welcome, too.

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.

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

Granary Cottage with access to indoor pool & spa

60% off June mid-weeks. Private Heated Pool.

Modern inner city 3 bed eco house

Boundary Court Barn, Selsley common, Stroud

Cotswold Farmhouse with Swimming Pool

Cotswolds Cottage, Heated Pool, Tithe Barn Views

The Moretons Farmhouse
Weekly house rentals

Colliers Cottage at The Barracks, Forest of Dean

Delightful 3-Bedroom cottage with log burner

School Cottage, next to Berkeley Castle

The Pink Cottage

Woodside Cottage, Cannop Heart of Forest of Dean

Super Chic trendy town house central Bedminster

Luxury Cotswolds Cottage, Castle Combe (optional Hot Tub)

Gardener's Cottage, part of a 16th century manor.
Private house rentals

Redland Suites: The Mews. Great Location & Sleep 4

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

The Courtyard Barn overlooking Monmouth.

Romantic rural barn nestled in The Mendip Hills

3 Bed Coachhouse, Courtyard & Driveway

Redwood House - Free Parking

Luxury Woodland Spa | Hot Tub & Sauna | Sleep 6

Wye Valley Retreat | Deer Garden & River Views
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
- Puzzlewood
- No. 1 Royal Crescent
- Dunster Castle
- St Audrie's Bay
- Newton Beach - Porthcawl
- Eastnor Castle
- Hereford Cathedral
- National Showcaves Centre for Wales
- Longleat Safari Park





