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

Total vacation rentals
Explore 20 vacation rentals in Chepstow

Nightly prices starting at
Chepstow vacation rentals start at G$2,092 GYD per night before taxes and fees

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Over 670 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Wi-Fi availability
20 of Chepstow vacation 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.

Colliers Cottage at The Barracks, Forest of Dean
Situated in the heart of the Forest of Dean, you will find Colliers Cottage. An ex-colliers cottage that has been extensively renovated in 2024, it comprises 2 bedrooms (1 with en-suite), family bathroom, kitchen, lounge (with sofa bed), dining room and a large, fully fenced private garden with off road parking If you want a stay where you are surrounded by nature, look no further! This is an ideal location for keen walkers, runners and cyclists with off road trails just a short distance away

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

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.

Forest Cottage
There are no hidden extra payments, the nightly fee is total. Self catering cottage, originally built in the 1800's, restored and extended to provide a high standard of accommodation. Set in private gardens which extend to 23 acres and with outstanding views across the Usk valley. The garden area provides 2 large decked viewpoints, Private parking. The property has retained its original stone spiral staircase which might prove difficult for guests with mobility issues or the very young.

Cider Mill Monmouthshire.Views of Black Mountains
Beautiful converted Cidermill set in the Wye Valley, with stunning views of the Black Mountains, quiet rural location three miles from the historic town of Monmouth, therefore we are not suitable for party people. Also not far from The Forest of Dean and the mountain bike tracks, Ideally situated for country walks, comes with ample parking space for two or three cars. Short drive to several country inns and restaurants. What three words compound.quantity.roadways will bring you direct.

Oakwood Cottage, Cannop in heart of Forest of Dean
A 100-year old, semi detached cottage, set in the beautiful Oak woodlands of the Cannop Valley Nature Reserve. The family Cycle trail, XC trail, Enduro trail, DH trail and Pedalabikeaway Cycle Hire Centre are only 200 metres from the cottage. Cycle storage is available at the Cottage. Beechenhurst Lodge Picnic site, the Sculpture trail and the scenic Cannop Ponds are a short woodland walk away. Oakwood Cottage sleeps up to 7 guests and is pet friendly with a large enclosed garden.

Entire House . Self Catering . Almondsbury
Roylands Farm Cottage is located on a working farm, surrounded by countryside yet easy access to motorway networks. Ideally located for exploring Bristol and surrounding areas. The property allows sole use of entire house. The property has 5 bedrooms, four with en-suites, a family bathroom, a lounge with conservatory, Kitchen dinner with all cooking facilities available. A large private garden, with outdoor seating, BBQ and pizza oven for you to enjoy. Ample off road parking.

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.

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

Modern inner city 3 bed eco house

Boundary Court Barn, Selsley common, Stroud

The Warm Hearth: 18th century barn retreat.

Green Hat Stays - Chepstow - Harvax House

Luxury Countryside House | Spacious & Picturesque

The Old Rectory with Swimming Pool

Charmandene: 5-Bedroom Villa with Pool & Large Sec

Pwll Court Retreat, Swim Spa, sleeps 12 people
Weekly house rentals

Luxury In Langstone!

Monmouth Georgian owned by our family since 1923

School Cottage, next to Berkeley Castle

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

Portishead eco-home with a View

Bath Stone Retreat | City Views + Free Parking

Caithness Holiday Home

Pet friendly 3 Bed home ideal for families, groups
Private house rentals

Stylish barn in The Forest of Dean

A most unusual Manor House

Delightful 3-Bedroom cottage with log burner

Country Farmhouse | Hamlet Views & Walks from Door

The Pink Cottage

20fairview Chepstow

New 3 Bedroom Flat Close to Station

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





