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

Total vacation rentals
Explore 10 vacation rentals in Chepstow

Nightly prices starting at
Chepstow vacation rentals start at ﺩ.ﺇ 37 per night before taxes and fees

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Over 600 verified reviews to help you choose

Wi-Fi availability
10 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.

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

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.

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

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.

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

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.

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.
Popular amenities for Chepstow house rentals
House rentals with a pool

Maple cottage

Granary Cottage with access to indoor pool & spa

The Old Rectory with Swimming Pool

Amazing 40% off JULY mid-weeks in the Cotswolds

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
Weekly house rentals

Stunning 17th century Cotswolds townhouse annexe

Unique Cosy Retreat - Spacious 3-Bed Farm House

The Loft House - Beautiful House in Best Location

Forest Cottage

Luxury Cotswolds Cottage, Castle Combe (optional Hot Tub)

Cider Mill Monmouthshire.Views of Black Mountains

Willsbrook Lodge

Charming end of terrace 2 bed country cottage
Private house rentals

Large Luxurious & Picturesque Countryside House

Delightful 3-Bedroom cottage with log burner

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

The Pink Cottage

The Roundhouse

Luxury Woodland Spa | Hot Tub & Sauna | Sleep 6

Wye Valley Retreat | Deer Garden & River Views

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





