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
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 7 nights From £475

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 7 nights From £475

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From £484

  • Sleeps3
  • Bedrooms2
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Washing machine
  • Baby-friendly


for 7 nights From £317

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

Horse Gin is a charming, pet-friendly cottage situated in Parkend, Gloucestershire, with a mezzanine bedroom, open-plan living, and an enclosed patio. Monmouth 10.8 miles; Ross-on-Wye 12.8 miles; Symonds Yat 12.8 miles. (Ref. 1195950)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Washing machine


for 7 nights From £439

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    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


for 7 nights From £648

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

The Foxes Den is a welcoming, single-storey Shepard's hut resting in the rural Shepperdine, a village in Gloucestershire. Countryside. Woodburning stove. Thornbury 5.7 miles; Chepstow 15 miles; Stroud 20.6 miles. (Ref. 1151420)

  • Pets go free
  • Ground floor bedroom


for 7 nights From £341

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    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)

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


for 7 nights From £429

Last booked yesterday
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  • Sleeps3
  • Bedrooms2
  • Pet FriendlyNo

    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 From £449

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Ground floor bedroom
  • Dishwasher


for 7 nights From £416

  • Sleeps9
  • Bedrooms5
  • Pet FriendlyNo

    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 From £709

  • Sleeps5
  • Bedrooms3
  • Pet FriendlyYes

    4.5

    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)

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


for 7 nights From £533

Last booked yesterday
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  • Sleeps3
  • Bedrooms1
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • 20% off - Mon 3rd Aug to 10th Aug 2026

  • 20% off - Mon 17th Aug to 24th Aug 2026

  • 15% off - Mon 24th Aug to 31st Aug 2026


for 7 nights From £289

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    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 From £450

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 7 nights From £633