Holiday Cottages in Chepstow

Your Chepstow/Cas-Gwent, Monmouthshire search returned 36 cottages

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A property's star rating is the average of the star ratings received from guests that wish for their review to be published

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    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


for 7 nights €548

  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Castle Rag is a charming, single-storey, pet-friendly cottage in Parkend, Gloucestershire, offering an open-plan living space and a secure patio. Monmouth 10.8 miles; Ross-on-Wye 12.8 miles; Symonds Yat 12.8 miles. (Ref. 1197901)

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


for 7 nights €504

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • 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


for 7 nights €515

  • 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


for 7 nights €574

Last booked yesterday
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  • Sleeps9
  • Bedrooms5
  • PetsNo

    4.3

    Good

  • Sykes rating

14 Birchwood Road is a wonderful, detached holiday home resting in the pretty little village of Woolaston in Gloucestershire with a woodburning stove. Chepstow 6.4 miles; Monmouth 12.4 miles; Ross-on-Wye 17.8 miles. (Ref. 1168522)

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


for 7 nights €822

  • 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


for 7 nights €521

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • 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


for 7 nights €455

Last booked yesterday
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  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A contemporary annexe resting in Woolaston, Gloucestershire. Open-plan. Close to amenities. Pet-friendly. Chepstow 5.9 miles; Monmouth 12.4 miles; Ross-on-Wye 19.7 miles. (Ref. 1102411)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher


for 7 nights €483

  • 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


for 7 nights €522

  • Sleeps3
  • Bedrooms1
  • PetsYes

    4.3

    Good

  • Sykes rating

The Snug, a peaceful, single-storey hut tucked away in the rural outskirts of Llanvair Discoed in Monmouthshire. Near to National Landscape. Studio-style. Caldicot 5.3 miles; Chepstow 8.3 miles; Tintern 11.3 miles; Cwmcarn 20.8 miles; Cardiff 23.9 miles. (Ref. 1158114)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • 10% off - Mon 3rd Aug to 10th Aug 2026

  • 10% off - Mon 10th Aug to 17th Aug 2026

  • 10% off - Mon 17th Aug to 24th Aug 2026

  • 10% off - Mon 24th Aug to 31st Aug 2026


for 7 nights €336

  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Woods Cottage is a traditional farmhouse set in Kingcoed near Raglan, Sir Fynwy, complete with a woodburning stove, a hot tub, and a welcome for pets. Usk 5.5 miles; Monmouth 8.9 miles; Abergavenny 12.5 miles. (Ref. 1152870)

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


for 7 nights €619

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A charming private apartment situated in the vibrant town of Lydney in Gloucestershire. Pet friendly. Off-road parking. Balcony. Chepstow 8.9 miles; Monmouth 11.8 miles; Gloucester 19.9 miles. (Ref. 1065656)

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


for 7 nights €716