
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 $17 NZD 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.

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
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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.
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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.
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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
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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.
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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.
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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.
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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.
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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.
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Fuchsia Barn, romantic Cotswolds
Fuchsia Barn is a brand new purpose built Airbnb unit, finished to a very high standard, with lots of natural materials giving it a relaxing and cosy atmosphere. It is situated 12 minutes walk from the beautiful village of Castle Combe, often voted the prettiest in the country, and featured in many films. There are wonderful woodland walks from the property, and two village pubs within walking distance
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Cosy Private Studio. Fast Wi-Fi & Parking.
A cosy, modern studio in Caldicot- perfect for solo professionals or couples*, looking for a comfortable home base. Enjoy smart design, high-speed Wi-Fi. ✨ The Space Compact open-plan area with sofa bed, Smart TV and dedicated workspace Dishwasher, microwave, and plug-in appliances. En-suite shower room with modern fittings Mezzanine sleeping area with double bed & second Smart TV
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The Loft House - Beautiful House in Best Location
The Loft House is a charming, newly renovated house in the heart of Bath . A host of lovely cafes, restaurants and independent shops are right on the doorstep. The historic Circus is a stone's throw away with the Royal Crescent a short walk beyond. Heading south, you'll quickly reach Milsom Street which will take you down towards the Roman Baths, Abbey and Pulteney Bridge.
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Popular amenities for Chepstow house rentals
House rentals with a pool

Boundary Court Barn, Selsley common, Stroud
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Modern inner city 3 bed eco house
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Private Pool/Cotswolds/Gatherings/Slps 12/Games Rm
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The Warm Hearth: 18th century barn retreat.
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Large Luxurious Picturesque Countryside House
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The Old Rectory with Swimming Pool
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Charmandene: 5-Bedroom Villa with Pool & Large Sec
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Buckstone House Coach House
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Weekly house rentals

The Game Larders
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Stylish barn in The Forest of Dean
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Unique Cosy Retreat - Spacious 3-Bed Farm House
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Stunning Lansdown Crescent Mews House with parking
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Charming end of terrace 2 bed country cottage
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Beautiful Barn near Bristol in Picturesque Setting
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Dry Dock Cottage
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Forest Cottage
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Private house rentals

A most unusual Manor House
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The Pink Cottage
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Delightful 3-Bedroom cottage with log burner
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New 3 Bedroom Flat Close to Station
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20fairview Chepstow
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Spacious 2 bed/Scenic location, Parking
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Country Farmhouse | Hamlet Views & Walks from Door
LocationFamilyNearby

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





