Popular Features
Sleeps
Sleeps
Destinations
Popular Cottages
- Bears Court Unit 7
- Quarry Lodge in Munsley
- Cow Byre
- Bustard Hut in Cholderton
- Hillside Barn
- Bears Court Unit 4
- Cider Mill in Garway Hill
- The Brook at Mirrorbrook
- Estuary View Minsterworth
- Poppy Cottage at Manor Farm
- Moors Farm
- Wye Valley Manor
- Shepherds Hut Retreat in Alderbury
- The Royal Forest Lodge
- Oak Villa in Drybrook
- Plough Share in Gloucester
- The Lakeside Yurt
- Coach House Cottage
- Kingfisher Lodge in Glastonbury
- The Cottage
- Pippin in Pilton
- The Dairy at Applebarn Holidays
- The West Wing
- No. 1 Valley View Cottage
- Cotswold Valley View
- Rockstowes House
- The Annex at The Oaks
- Ardens Court Farmhouse
- Greenways Cottage
- Church Farm Barns 4
Chepstow Holiday Cottages
Our curated collection of Chepstow cottages has something for everyone... Whether you're idea of a great holiday is a modern glamping pod, or a rustic thatched cottage that's a hundred years old, we've got you covered! Each of our rentals features a private hot tub and everything you need for your next family holiday, romantic retreat or that getaway with a group of friends. Discover find your perfect Chepstow holiday home today.
- Private hot tub with views
- Wheelchair accessible ground floor
- Games room entertainment
- England Wales border location
- Wildlife watching opportunities
View Cottage
[+] To Favourites
Visitor Rating
4.5
- Private hot tub with views
- Ground floor barn conversion
- Secure dog exercise paddock
- Forest of Dean location
- Near Chepstow Castle attractions
View Cottage
[+] To Favourites
- Private hot tub for six
- Ground floor cottage layout
- England Wales border location
- Games room with pool table
- Private parking three cars
View Cottage
[+] To Favourites
Visitor Rating
4.8
- Private hot tub with views
- Ground floor easy access
- Enclosed garden for pets
- Minutes from Tintern Abbey
- Stunning Wye Valley location
View Cottage
[+] To Favourites
Visitor Rating
5
- Private wood-fired hot tub
- Secluded meadow location
- Luxury king-size bed
- Wildlife watching opportunities
- Excellent hosts
View Cottage
[+] To Favourites
Visitor Rating
4.9
- Private hot tub garden
- Four bedrooms with TVs
- Woodburner and cosy living
- Enclosed garden and barbecue
- Walking from your doorstep
View Cottage
[+] To Favourites
- Private hot tub with countryside views
- Wood burner and vaulted ceilings
- Two en-suite bedrooms sleeping four
- Trails from doorstep Forest of Dean
- Welcomes up to four dogs
- Secure parking and bike storage
View Cottage
[+] To Favourites
Visitor Rating
4.9
- Panoramic River Severn views
- Hot tub on private terrace
- Sleeps 20 across 7 bedrooms
- Three acres of beautiful gardens
- Basement games room with karaoke
View Cottage
[+] To Favourites
Visitor Rating
4.9
- Seven-seater hot tub with river views
- Spotlessly clean modern accommodation
- Two bedrooms plus sofa bed
- Enclosed garden with fire pit
- Close to Forest of Dean trails
View Cottage
[+] To Favourites
Visitor Rating
4.8
- Private hot tub
- Tennis court on site
- Sleeps up to 10 guests
- Dog walking field
- Perfect for celebrations
View Cottage
[+] To Favourites
Visitor Rating
4.8
- Private hot tub
- Peaceful forest location
- King-size bed with luxury linens
- Large rainfall shower
- Direct access to forest walks
View Cottage
[+] To Favourites
Visitor Rating
4.6
- Shared hot tub access
- Forest of Dean location
- Pet-friendly accommodation
- Private parking space
- Near Go Ape adventure
View Cottage
[+] To Favourites
Visitor Rating
4.7
- Shared hot tub access
- Forest of Dean location
- Pet friendly accommodation
- Private parking included
- On-site horse riding facilities
View Cottage
[+] To Favourites
Visitor Rating
4.8
- Hot tub with forest views
- King-size bed with quality linens
- Woodburning stove for cosy evenings
- Walks direct from the door
- Fully equipped modern kitchen
View Cottage
[+] To Favourites
Visitor Rating
5
- Sleeps 20 guests comfortably
- Private hot tub for six
- Huge enclosed garden space
- Ground floor accessibility throughout
- Near Bristol and Bath
View Cottage
[+] To Favourites
Visitor Rating
5
- Sleeps 24 guests comfortably
- Private hot tub for six
- Games room and garden
- Parking for 10 cars
- Near Bristol and Bath
View Cottage
[+] To Favourites
Visitor Rating
4
- Grade II listed royal history
- Swimming pool and hot tub
- Cinema room with surround sound
- Secret door in library
- Forest of Dean location
View Cottage
[+] To Favourites
- Private hot tub on deck
- Forest of Dean 10-minute walk
- Three en-suite bedrooms sleep six
- Open-plan living 1100 square feet
- Electric vehicle charging available
View Cottage
[+] To Favourites
- Private hot tub in woodland setting
- Both bedrooms with ensuite bathrooms
- Open-plan living with media wall
- Decked terrace with forest views
- Electric vehicle charging available
View Cottage
[+] To Favourites
- Private hot tub on decked area
- Three bedrooms sleeping six guests
- Two dogs welcome with gardens
- Forest of Dean location for walks
- Electric vehicle charging point available
View Cottage
[+] To Favourites
- Private hot tub on decking
- Four bedrooms sleeping eight guests
- Forest of Dean walking trails nearby
- Enclosed garden for two dogs
- Golf club estate setting Gloucestershire
View Cottage
[+] To Favourites
- Private hot tub with orchard views
- Heated indoor pool by arrangement
- Sleeps 7 across 4 bedrooms
- Parking for 8 cars included
- Forest of Dean 8 miles away
View Cottage
[+] To Favourites
Visitor Rating
4.7
- Private wood-fired hot tub
- Peaceful countryside location
- Fully equipped compact studio
- Underfloor heating throughout
- Close to Cotswolds and Bristol
View Cottage
[+] To Favourites
Visitor Rating
4.7
- Private hot tub with valley views
- Dog-friendly accommodation for two pets
- Excellent Forest of Dean location
- Clean and comfortable living spaces
- Easy access to outdoor activities
View Cottage
[+] To Favourites
- Grade II listed historic cottage
- Private hot tub for six
- Working sheep farm setting
- Three bedrooms sleep six
- Private parking three cars
View Cottage
[+] To Favourites
Visitor Rating
4.8
- Private hot tub
- Enclosed pet-friendly garden
- Games room with table tennis
- Luxury 5-star accommodation
- Perfect Forest of Dean location
View Cottage
[+] To Favourites
Visitor Rating
4.8
- Stunning Severn estuary views
- Private hot tub
- Games room with multiple activities
- Six spacious bedrooms
- Large enclosed garden
View Cottage
[+] To Favourites
Visitor Rating
5
- Grade II listed manor house
- Hot tub for seven people
- Private heated swimming pool
- Ten bedrooms sleep eighteen
- Seven acres private grounds
View Cottage
[+] To Favourites
- Private hot tub for seven
- Heated swimming pool included
- Grade II Listed manor house
- Seven acres of grounds
- Sleeps eight across five bedrooms
View Cottage
[+] To Favourites
Visitor Rating
4.8
- Private hot tub with amazing views
- Dog-friendly with enclosed garden
- Direct access to Cotswold Way
- Short walk to town pubs
- Cosy interior with underfloor heating
View Cottage
[+] To Favourites
Explore more of Gloucestershire
Popular towns and villages in and around Chepstow
Ashton Keynes Badminton Berkeley Bibury Blockley Brockweir Brockworth Cambray Cheltenham Chipping Campden Chipping Sodbury Cirencester Coleford Dangan Deerhurst Ellwood Evenlode Fairford Fiddlers Green Gloucester Hawkesbury Highleadon Hinton Kempley Kingscote Lechlade Little Rissington Longborough Lower Swell Lydney Nailsworth Northway Notgrove Oddington Owlpen Painswick Sandford Sapperton Shipton Moyne Snowshill Somerford Keynes South Cerney Southrop Stonehouse Stroud Sudeley Sudgrove Swell Swindon Symonds Yat Tetbury Tewkesbury Thornbury Whiteway Whitminster Winchcombe