24/7 “On Holiday” Support

Our friendly UK team are here to help, in case of any emergency.

Award Winning Holiday Experts

Over 30 years of experience in UK self-catering holidays.

B Corp Certified Business

Committed to making a positive social and environmental impact.

Safe & Secure Payments

Flexible payment options for peace of mind.

Holiday Cottages in Chepstow

REFINE SEARCH

Your Chepstow/Cas-Gwent, Monmouthshire search returned 33 cottages

Most relevant
  • Distance to Location
  • Most relevant
  • Price (lowest first)
  • Price (highest first)
  • Sleeps (lowest first)
  • Sleeps (highest first)
  • Tick Rating (lowest first)
  • Tick Rating (highest first)
20
  • 10
  • 20
  • 50
  • 100
  • Sleeps8
  • Bedrooms3
  • PetsNo

    5.0

    Perfect

  • Sykes rating

An idyllic, characterful cottage near Chepstow, Monmouthshire. Electric flame-effect stove. Countryside views. In the Wye Valley AONB. Original features. Monmouth 15.1 miles; Bristol 21.4 miles; Newport 21.4 miles. (Ref. 1118276)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Baby-friendly

7 nights from £667

Last booked yesterday
See more details
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A charming detached barn conversion, close to Oldbury-on-Severn in Gloucestershire. Exposed beams. En-suite. Ground-floor bedroom. (Ref. 1011610)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Washing machine
  • Baby-friendly

7 nights from £604

  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A high quality, detached cottage set in beautiful surroundings with wonderful views. Heavenly! Convenient for touring (or relaxing) the Cotswolds, Wye Valley and Forest of Dean (Ref. 988783)

  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £552

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A beautifully presented cottage in the lovely village of St. Briavels near Lydney in Gloucestershire. Stunning gardens. Conservatory. TV. Upside down layout. Pub 5 mins walk. St. Briavels Castle. (Ref. 985313)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher

7 nights from £366

Last booked yesterday
See more details
  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Thoughtfully designed and extended luxury accommodation with stunning views over the Wye Valley. Fabulous! (Ref. 990342)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room

7 nights from £928

Last booked yesterday
See more details
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

An immaculately presented character first-floor apartment in converted Grade II listed coach house in Lydney, Gloucestershire. Off-road parking. Near Forest of Dean. Open-plan. Chepstow 9 miles; Ross-on-Wye 16 miles; Gloucester 20.8 miles. (Ref. 1065654)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

7 nights from £452

  • Sleeps10
  • Bedrooms5
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A contemporary, five-bedroom home resting on farmland in the village of Aust, Gloucestershire. Countryside views. EV charging point. Hot tub. Large. Family-friendly. Stylish. Thornbury 6.6 miles; Bristol 11.5 miles; Weston-Super-Mare 26.2 miles. (Ref. 1124276)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Ground floor bedroom
  • Hot Tub
  • Dishwasher
  • Washing machine

7 nights from £1583

  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Perfect

  • Sykes rating

A delightful single-storey annex nestled in Stroat, Gloucestershire. Ground-floor living. Countryside views. Romantic. Monmouth 14.8 miles; Bristol 21.6 miles; Newport 23.6 miles. (Ref. 1083768)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Hot Tub
  • Dishwasher

7 nights from £585

Last booked yesterday
See more details
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A characterful cottage resting on the outskirts of Lydney, Gloucestershire. Off-road parking. Pet-friendly. WiFi. Chepstow 9 miles; Ross-on-Wye 16 miles; Gloucester 20.8 miles. (Ref. 1057990)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £444

Last booked yesterday
See more details
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

A single-storey cottage in the village of Llandenny near Raglan in Monmouthshire. Suitable for people with mobility issues. WiFi. Raglan 2 miles, Usk 4.9 miles, Chepstow 8.6 miles, 16.9 miles. (Ref. 983854)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Washing machine
  • Baby-friendly

7 nights from £419

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A superb all ground floor barn conversion with countryside views. Walks and bike rides from the door. In the Forest of Dean. Clearwell 5.5 miles. (Ref. 921012)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Washing machine

7 nights from £441

  • Sleeps3
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A semi-detached cottage in the village of Llandenny near Raglan in Monmouthshire. Contemporary interior. WiFi. Raglan 2 miles, Usk 4.9 miles, Chepstow 8.6 miles, 16.9 miles. (Ref. 983855)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Washing machine
  • Baby-friendly

7 nights from £418

  • Sleeps10
  • Bedrooms5
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A wonderful detached cottage in village of Parkend, within the Royal Forest of Dean. Underfloor heating throughout. En-suite facilities. Pet-friendly. Games area. Cinderford 6.7 miles; Monmouth 9.8 miles; Ross-on-Wye 12.8 miles. (Ref. 1062726)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £1053

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

This stunning property is situated in Pill, Somerset. WiFi. Pet-friendly. Enclosed terrace. Bristol 6.5 miles; Mendip Hill AONB 18.4 miles. (Ref. 1004304)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £480

  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A special, converted old chapel resting in the village of Bream, close to the Forest of Dean. Open-plan living. Ideal for families. Garden patio. Coleford 4.2 miles; Lydney 3.4 miles. (Ref. 1071356)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

7 nights from £839

  • Sleeps10
  • Bedrooms5
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

This charming, semi-detached, three-storey holiday home resting in Tutshill near Chepstow, Monmouthshire. Off-road parking. Pet-free. Woodburning stove. Close to amenities. Enclosed garden. Monmouth 15.6 miles; Bristol 18.9 miles; Newport 19.2 miles. (Ref. 1093054)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Games room

7 nights from £797

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A beautifully presented romantic cottage in the heart of Whitcroft, Gloucestershire. Edge of forest. Hot tub. Woodburner. Monmouth 7 miles. (Ref. 991699)

  • Wi-fi
  • Off-road parking
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Sky TV

7 nights from £523

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A lovely three-bedroom bungalow resting on the outskirts of Lydney, Gloucestershire. Pet-friendly. Private garden/ Off-road parking. Close to amenities. Chepstow 10.2 miles, Monmouth 13.6 miles; Gloucester 20.2 miles (Ref. 1120525)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £393

Last booked yesterday
See more details
  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A cosy detached stone-built cottage in the village of Trellech. Situated in Area of Outstanding Natural Beauty ideal for walking and cycling. Pet-friendly. Monmouth 6 miles. (Ref. 938052)

  • Wi-fi
  • Off-road parking
  • Washing machine
  • Baby-friendly

7 nights from £323

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A superb, refurbished first-floor apartment in a Grade II listed coach house in Lydney, Gloucestershire. Off-road parking. WiFi. Pet-friendly. Close to amenities. Chepstow 9 miles; Ross-on-Wye 16 miles; Gloucester 20.8 miles. (Ref. 1065655)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

7 nights from £445

Resting alongside the River Wye, with striking views of the limestone cliffs, this bustling town has a large range of Chepstow accommodation to use as your base for touring this stunning part of Wales.

Why Chepstow?

Bordering Gloucestershire, Chepstow benefits from a large selection of traditional eateries for that fine dining experience and many independent shops. The town hosts five Grade I listed buildings, several of which have Grade II* listed status and is hugely popular with tourists for Chepstow Racecourse, which hosts 32 racing fixtures throughout the year, including the Welsh Grand National. Explore the town's historic past at the Chepstow Museum, spot its Georgian and Victorian buildings, as well as the award-winning redevelopment areas, before returning to your homely holiday cottage in Chepstow. For more information on what you can get up to in the area, take a look at our Wales Travel Guide for inspiration.

Places to Visit near Chepstow

A Chepstow cottage is the ideal choice due to its ideal placement within reach of many tourist hot spots. Let's not forget the town's close proximity to the Wales Coast Path offering wonderful panoramic views and ample birdwatching opportunities. The town rests close to the Wye Valley for long rural walks and some historic locations such as Tintern Abbey dating back to the 12th century and the medieval Goodrich Castle. Also available is the Wye Valley Walk and the Wye Valley Butterfly Zoo, something your little ones will delight in. Take a drive towards the thriving capital city of Wales, Cardiff, which gives access to the Gothic Cardiff Castle, notable Cardiff Bay and even Cardiff Golf Club. Make sure you explore Abergavenny, Cardiff, Newport and Wye Valley on your journey, all reachable from your Chepstow accommodation.

Types of Holiday

If it's a coastal break you're interested in, then explore our list of coastal holiday cottages in Wales for an extensive range of options. Don't forget to bring the family pet along and view our dog-friendly cottages in Wales to treat the whole family to a break! Looking for a holiday soon? Fear not, our list of last-minute cottages in Wales is sure to inspire you to book your next break today! Uncover more of the area from these South Wales cottages.

Once you've found your perfect Chepstow accommodation, be sure to secure your booking with us today, with a range of handy travel experts on-hand to help guide you.