Holiday Cottages in Chepstow

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Holiday Cottages in Chepstow

REFINE SEARCH

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

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Map View
A driveway with a stone wall building on the left and a black house with a red roof on the right at The Snug in Llanvair Discoed near Caerwent
Offer
15
Llanvair Discoed near Caerwent, Monmouthshire, NP16
  • Sleeps3
  • Bedrooms1
  • PetsYes

    4.6

    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

  • £100 off - Fri 25th Jul to 1st Aug 2025

  • £120 off - Fri 1st Aug to 8th Aug 2025

  • £136 off - Fri 8th Aug to 15th Aug 2025

7 nights from £317

Last booked yesterday
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A wooden shepherds hut with a raised deck and stairs in a grassy area surrounded by trees at The Foxes Den Shepherds Hut in Oldbury-On-Severn
27
Oldbury-On-Severn, Gloucestershire, BS35
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    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

7 nights from £357

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A single story building with a tiled roof and fenced patio with an umbrella and chairs surrounded by trees at Bottom Lodge in Penhow
19
Penhow, Monmouthshire, NP16
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    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

7 nights from £463

Last booked 3 days ago
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A stone cottage with a small patio and outdoor table and chairs with potted plants at The Pound in Trellech near Monmouth
23
Trellech near Monmouth, Monmouthshire, NP25
  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.7

    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 £333

Last booked yesterday
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Exterior view of a single-story house with a gravel driveway and windows at The Honey Pot in Stroat near Chepstow
29
Stroat near Chepstow, Gloucestershire, NP16
  • Sleeps2
  • Bedrooms1
  • PetsNo

    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 £533

Last booked 5 hours ago
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A stone building with arched windows and a fenced front yard with an orange umbrella at The Old Sunday School in Bream
36
Bream, Gloucestershire, GL15
  • Sleeps8
  • Bedrooms4
  • PetsNo

    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

Last booked 2 days ago
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A house with a sloped roof surrounded by bushes and a grassy area at Rose Cottage in Bream
31
Bream, Gloucestershire, GL15
  • Sleeps4
  • Bedrooms2
  • PetsYes

    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

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A small house with roof covered in red and green leaves surrounded by grass and trees at The Piggery in Lydney
29
Lydney, Gloucestershire, GL15
  • Sleeps5
  • Bedrooms3
  • PetsNo

    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 £562

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An exterior view of a white house with a tiled roof a garden with grass flowers a stone wall and a gravel path at Avonside Cottage in Pill Somerset
28
Pill, Somerset, Somerset, BS20
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    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 £450

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An outdoor patio with wicker furniture a chessboard playing cards and potted plants overlooking a green landscape at The Grooms in Lydney
36
Lydney, Gloucestershire, GL15
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    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

7 nights from £627

Last booked 9 hours ago
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An outdoor covered seating area with two wicker chairs a matching table and a potted palm at The Tack Room in Lydney
52
Lydney, Gloucestershire, GL15
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    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 £494

Last booked yesterday
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A stone house exterior with green framed windows and doors and plants at The Stable in Lydney
44
Lydney, Gloucestershire, GL15
  • Sleeps4
  • Bedrooms2
  • PetsYes

    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

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A living room with a leather sofa cushions a fireplace wall-mounted tv and a kitchen bar with stools at The Carriage in Lydney
42
Lydney, Gloucestershire, GL15
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    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 £461

Last booked yesterday
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A stone house with white windows and door behind a stone wall and open gate at About Time Cottage in Parkend
47
Parkend, Gloucestershire, GL15
  • Sleeps10
  • Bedrooms5
  • PetsYes

    4.8

    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

Last booked today
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A brick building with black doors and windows a concrete pathway green grass and a flower pot at The Pheasant Two in Raglan
28
Raglan, Monmouthshire, NP15
  • Sleeps3
  • Bedrooms2
  • PetsNo

    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 £432

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A garden with a wooden picnic table and patio furniture outside a stone and wood building with trees in the background at The Stable @ Rose Cottage in Yorkley
20
Yorkley, Gloucestershire, GL15
  • Sleeps4
  • Bedrooms2
  • PetsYes

    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 £426

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Exterior of a two story stone cottage with garden, trees, shrubs, bench, and a pathway at The Cottage in St Briavels
33
St Briavels, Gloucestershire, GL15
  • Sleeps8
  • Bedrooms4
  • PetsYes

    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

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An exterior view of a stone and wood barn with a tiled roof and flower pots around Golden Valley Barn Oldbury-On-Severn
33
Oldbury-On-Severn, Gloucestershire, BS35
  • Sleeps4
  • Bedrooms2
  • PetsNo

    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

Last booked yesterday
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A stone house with a tiled roof surrounded by trees and bushes at The Generals Cottage in Penallt Wye Valley
8
Penallt, Wye Valley, Monmouthshire, NP25
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Sykes Rating

A beautifully-presented rural cottage set in the heart of the Wye Valley, with lovely walks from the doorstep and two lovely village inns serving excellent food and local ales. Monmouth 6 miles. (Ref. 13460)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £429

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A living room with a sofa armchairs coffee table dining table and chairs at The Annexe in Yorkley
17
Yorkley, Gloucestershire, GL15
  • Sleeps3
  • Bedrooms1
  • PetsYes

    4.5

    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

7 nights from £348

Last booked 2 days ago
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Map View

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.