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
  • 8 Guests
  • 4 Bedrooms
  • Pets No

    4.9

    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 £818

  • 10 Guests
  • 5 Bedrooms
  • Pets Yes

    4.7

    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 £1175

  • 10 Guests
  • 5 Bedrooms
  • Pets No

    4.8

    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
  • Baby-friendly

7 nights from £1482

Last booked 2 days ago
See more details
  • 10 Guests
  • 3 Bedrooms
  • Pets No

    4.9

    Sykes Rating

Hidden Well is a luxury detached holiday home situated in the charming village of Pilning, Gloucestershire. Private parking. Hot tub. EV charging. Thornbury 6.5 miles; Bristol 12.1 miles; Weston-super-Mare 26.5 miles (Ref. 1150111)

  • Wi-fi
  • Electric vehicle charging
  • Ground floor bedroom
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £1276

  • 2 Guests
  • 1 Bedroom
  • Pets No

    4.8

    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 £488

Last booked 3 hours ago
See more details
  • 10 Guests
  • 5 Bedrooms
  • Pets No

    4.7

    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 £774

  • 2 Guests
  • 1 Bedroom
  • Pets No

    5.0

    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 £588

Last booked yesterday
See more details
  • 4 Guests
  • 2 Bedrooms
  • Pets No

    4.9

    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 £623

  • 8 Guests
  • 4 Bedrooms
  • Pets Yes

    4.7

    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 £897

  • 4 Guests
  • 2 Bedrooms
  • Pets Yes

    4.8

    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 £442

  • 6 Guests
  • 3 Bedrooms
  • Pets No

    4.7

    Sykes Rating

A stunning cottage placed on the outskirts of the lovely village of Bream in the Gloucestershire. Countryside views. Conservatory. Lydney 4 miles. (Ref. 966511)

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

7 nights from £457

  • 5 Guests
  • 3 Bedrooms
  • Pets No

    4.8

    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 £554

Last booked 2 hours ago
See more details
  • 2 Guests
  • 1 Bedroom
  • Pets No

    4.8

    Sykes Rating

A fabulous converted bull pen situated in the rural countryside of Llansoy near Raglan. Breath-taking views. Romantic retreat. Garden with barbecue. Usk 7.2 miles; Monmouth 10.7 miles; Abergavenny 15.4 miles. (Ref. 1010598)

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

7 nights from £426

  • 4 Guests
  • 2 Bedrooms
  • Pets Yes

    4.9

    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 £406

Last booked yesterday
See more details
  • 4 Guests
  • 2 Bedrooms
  • Pets No

    4.9

    Sykes Rating

The Fountain Lodge is a delightful lodge in the village of Parkend in Gloucestershire. En-suite bedrooms. Near the Forest of Dean. Close to amenities. Monmouth 10.1 miles; Symonds Yat 11.1 miles; Ross-on-Wye 12.9 miles. (Ref. 1158591)

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

7 nights from £449

  • 4 Guests
  • 2 Bedrooms
  • Pets No

    4.8

    Sykes Rating

Well-presented detached cottage located in the village of Bream, in Gloucestershire. Conservatory. Woodburner. Underfloor heating. Modern. Shop and pub 10 mins walk. (Ref. 989628)

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

7 nights from £425

  • 4 Guests
  • 2 Bedrooms
  • Pets Yes

    4.7

    Sykes Rating

A beautiful oak-clad lodge resting in Llanvair-Discoed, Monmouthshire. Near Wye Valley AONB. Private garden. Off-road parking. Barbecue. Caldicot 5.3 miles; Newport 11.6 miles; Cardiff 23.9 miles. (Ref. 1112486)

  • Wi-fi
  • Off-road parking
  • Hot Tub
  • Dishwasher
  • Washing machine
  • 10% off - Fri 25th Apr to 3rd May 2025

  • 10% off - Fri 9th May to 17th May 2025

  • 15% off - Sat 17th May to 25th May 2025

  • 10% off - Sun 25th May to 1st Jun 2025

  • 10% off - Sun 1st Jun to 9th Jun 2025

  • 10% off - Mon 9th Jun to 17th Jun 2025

  • 10% off - Tue 17th Jun to 25th Jun 2025

  • 10% off - Fri 1st Aug to 16th Aug 2025

  • 10% off - Sat 16th Aug to 24th Aug 2025

7 nights from £438

Last booked 2 days ago
See more details
  • 4 Guests
  • 2 Bedrooms
  • Pets Yes

    4.9

    Sykes Rating

A lovely, semi-detached cottage located in the charming village of The Narth near Trellech in Monmouthshire. Countryside setting. Log-effect fire. WiFi. Monmouth 6.1 miles; Chepstow 12.8 miles; Ross-on-Wye 18.7 miles. (Ref. 1025887)

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

7 nights from £354

  • 3 Guests
  • 2 Bedrooms
  • Pets No

    4.9

    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 £431

7 nights from £495

Last booked 2 days ago
See more details

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.