
House holiday rentals in Chepstow
Find and book unique houses on Airbnb
Quick stats about house rentals in Chepstow

Total holiday rentals
Explore 20 holiday rentals in Chepstow

Nightly prices starting at
Chepstow holiday rentals start at $14 AUD per night before taxes and fees

Verified guest reviews
Over 670 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Wi-Fi availability
20 of Chepstow holiday rentals include Wi-Fi 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!
Top-rated house rentals in Chepstow
Guests agree: These houses are highly rated for location, cleanliness and more.

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.

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

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.

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.

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.

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.

Stunning Lansdown Crescent Mews House with parking
Lansdown Crescent is a well-known example of Georgian architecture and a short walk from the famous Royal Crescent. Sitting quietly behind this iconic address you'll find this beautifully converted, lavish Upper Lansdown Mews house. Just a ten minute saunter from Bath centre, this truly luxurious two-bedroom retreat is brimming with the finest fixtures and finishes, complimented by a private terrace, mood lighting, carefully chosen furniture and artwork aplenty.

Stunning, stone property with city views
Immaculately presented two bedroom property located moments from the bustling city streets. This stunning property has the most beautiful views from the terrace, overlooking the UNESCO city of Bath, large living and dining spaces, two bedrooms both with ensuite bathrooms and off street parking. A real gem in the tranquility of elegant Widcombe with an abundance of local cafes, shops, pubs and restaurants only a short stroll away. Come, refresh and relax!

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.

Elegant Family-Friendly Retreat Stunning Views
Beautiful Family & Friends Retreat in the Wye Valley & Forest of Dean. 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 15% Airbnb fee
Popular amenities for Chepstow house rentals
House rentals with a pool

Olli's Summer House - Jacuzzi & Natural pool

Large Luxurious Picturesque Countryside House

The Old Rectory with Swimming Pool

Private Pool/Cotswolds/Gatherings/Slps 12/Games Rm

Green Hat Stays - Chepstow - Harvax House

The Warm Hearth: 18th century barn retreat.

Modern inner city 3 bed eco house

Boundary Court Barn, Selsley common, Stroud
Weekly house rentals

Colliers Cottage at The Barracks, Forest of Dean

Barton Suites- Luxury Home 1 of 2. Sleeps 6

Cosy Private Studio. Fast Wi-Fi & Parking.

Cotswolds Romantic Getaway in Luxury Barn

Country cottage with scenic views and hot tub

Beautiful Barn near Bristol in Picturesque Setting

Charming end of terrace 2 bed country cottage

The Game Larders
Private house rentals

Luxury Forest Hideaway with Four Poster Bed

Spacious 2 bed/Scenic location, Parking

Delightful 3-Bedroom cottage with log burner

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

The Pink Cottage

New 3 Bedroom Flat Close to Station

Luxury Woodland Spa | Hot Tub & Sauna | Sleep 6

Wye Valley Retreat | Deer Garden & River Views
Destinations to explore
- Cotswolds AONB
- Bannau Brycheiniog National Park
- Stonehenge
- Lower Mill Estate
- Wye Valley Area of Outstanding Natural Beauty (AONB)
- Brean Beach
- Bike Park Wales
- Cheltenham Racecourse
- Roath Park
- Cardiff Bay
- Bath Abbey
- Cotswold Wildlife Park
- Zip World Tower
- Puzzlewood
- Sudeley Castle
- Bute Park
- No. 1 Royal Crescent
- Barry Island Beach
- St Audrie's Bay
- Waterfall Country
- Eastnor Castle
- Newton Beach - Porthcawl
- Hereford Cathedral
- Caerphilly Castle





