
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

Verified guest reviews
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.

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
FamilyValueIndoor spaces

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.
LocationFamilyNearby

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.
ValueFamilyDecor

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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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.
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Redland Suites: The Mews. Great Location & Sleep 4
This beautiful 2-bedroom high spec mews house sleeps 4 guests comfortably. A gorgeous open plan fully equipped kitchen and living area, two bedrooms with king sized beds, both have luxury en-suite bathrooms one with a waterfall shower and the other with a bath. The property also has a downstairs toilet and utility room. These are just some of the features to make your stay perfect. The high-end finish and furniture has been selected with your comfort in mind.
LocationValueGetting around

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!
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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.
LocationFamilyCondition

Incline Cottage
As wildly romantic as it gets! With a wooded backdrop and canal side terrace, this larch-clad cottage is absolute luxury for two - with a sumptuous bed and statement slipper bath. Feel refreshed from the glorious views across the canal towards the mountains, or cosy up in front of the wood burner in the lounge. Unwind with a stroll along the canal towpath or stargaze together in the hot-tub. Pets are welcome, too.
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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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Popular amenities for Chepstow house rentals
House rentals with a pool

Olli's Summer House - Jacuzzi & Natural pool
LocationValueLong stay

Large Luxurious Picturesque Countryside House
LocationFamilySleep quality

The Old Rectory with Swimming Pool
LocationFamilyHospitality

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

Green Hat Stays - Chepstow - Harvax House
FamilyLocationIndoor spaces

The Warm Hearth: 18th century barn retreat.
LocationFamilyComfort

Modern inner city 3 bed eco house
FamilyValueLaundry

Boundary Court Barn, Selsley common, Stroud
FamilyLocationSleep quality
Weekly house rentals

Red Castle Lodge
ValueLocationSleep quality

Large Country Cottage, Log Fire, Fire Pit, Air Con
ValueFamilyIndoor spaces

Forest Cottage
LocationValueWifi

The Loft House - Beautiful House in Best Location
ValueFamilyCheckout

Luxury Cotswolds Cottage, Castle Combe (optional Hot Tub)
LocationFamilyComfort

Willsbrook Lodge
LocationValueNearby

Charming end of terrace 2 bed country cottage
FamilyLocationHeating

The Game Larders
ValueLocationRiver
Private house rentals

Luxury Forest Hideaway with Four Poster Bed
ValueFamilyOutdoor spaces

Delightful 3-Bedroom cottage with log burner
LocationFamilyBackyard

The Pink Cottage
ValueFamilyCondition

Scenic Wye Valley Retreat with Panoramic Views
FamilyLocationBathroom

New 3 Bedroom Flat Close to Station
LocationFamilyHospitality

Country cottage with scenic views and hot tub
LocationValueCondition

Wye Valley Retreat | Deer Garden & River Views
FamilyLocationAmenities

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





