Holiday Cottages in Chepstow

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

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  • 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 €492

  • 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 €555

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • 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


for 7 nights €405

  • Sleeps5
  • Bedrooms3
  • PetsYes
  • Sykes rating

Tawny Cottage is a charming cottage in Raglan, Monmouthshire, boasting a woodburning stove, countryside views and five acres of woodland to explore. Usk 5.5 miles; Monmouth 8.9 miles; Abergavenny 12 miles (Ref. 1183265)

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


for 7 nights €722

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

A stunning detached lodge perched in Llanvair-Discoed, Monmouthshire. Near Wye Valley AONB. Private garden. Off-road parking. Woodburning stove. Caldicot 5.3 miles; Newport 11.6 miles; Cardiff 23.9 miles. (Ref. 1117998)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Hot Tub
  • Dishwasher
  • Washing machine
  • 10% off - Sat 3rd Jan to 10th Jan 2026

  • 5% off - Sat 10th Jan to 17th Jan 2026

  • 5% off - Sat 17th Jan to 24th Jan 2026

  • 5% off - Sat 24th Jan to 31st Jan 2026

  • 5% off - Sat 31st Jan to 7th Feb 2026

  • 10% off - Sat 7th Feb to 14th Feb 2026

  • 10% off - Sat 14th Feb to 21st Feb 2026

  • 5% off - Sat 21st Feb to 28th Feb 2026

  • 5% off - Sat 28th Feb to 7th Mar 2026


for 7 nights €522

  • 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 €482

  • Sleeps2
  • Bedrooms1
  • PetsYes

    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)

  • Ground floor bedroom


for 7 nights €414

  • 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 €734

  • Sleeps9
  • Bedrooms5
  • PetsNo

    4.7

    Outstanding

  • 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 €809

  • Sleeps2
  • Bedrooms1
  • PetsYes
  • Sykes rating

Walnut Cottage is a romantic cottage in Raglan, Monmouthshire, featuring a woodburning stove, countryside views and access to five acres of woodland. Usk 5.5 miles; Monmouth 8.9 miles; Abergavenny 12 miles. (Ref. 1183268)

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


for 7 nights €418

Last booked 2 days ago
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  • Sleeps5
  • Bedrooms3
  • PetsYes
  • 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 €604

Last booked yesterday
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  • Sleeps3
  • Bedrooms1
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

The Annexe is a lovely, one-bedroom dwelling residing in Yorkley, Gloucestershire. Pet-friendly. Near an AONB. Ground-floor living. Close to amenities. Open-plan. Clearwell 5.6 miles; Symonds Yat 13.8 miles; Ross-on-Wye 15 miles. (Ref. 1138926)

  • Wi-fi
  • Ground floor bedroom
  • Washing machine
  • Baby-friendly


for 7 nights €404

  • Sleeps3
  • Bedrooms1
  • PetsYes

    4.2

    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 - Sun 4th Jan to 11th Jan 2026

  • 10% off - Sun 11th Jan to 18th Jan 2026

  • 10% off - Sun 18th Jan to 25th Jan 2026

  • 10% off - Sun 25th Jan to 1st Feb 2026


for 7 nights €357