Holiday Cottages in Chepstow

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We are delighted to announce that we have been awarded 'Best UK Holiday Cottage/Self Catering Booking Company' at the British Travel Awards.

Holiday Cottages in Chepstow

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Your Chepstow/Cas-Gwent, Monmouthshire search returned 35 cottages

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Map View
A living room with a fireplace a mirror a wooden coffee table sofas and a large window at Caradoc Tutshill near Chepstow
40
Tutshill near Chepstow, Gloucestershire, NP16
  • Sleeps10
  • Bedrooms5
  • PetsNo

    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 €894

Last booked 2 hours ago
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A backyard with green lawn a wooden pergola with a hot tub patio furniture and a modern house at Bilsham Meadows in Aust
53
Aust, Gloucestershire, BS35
  • Sleeps10
  • Bedrooms5
  • PetsNo

    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 €1762

Last booked yesterday
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The exterior entrance of a white house with stone walls a mailbox and the name Pippins on a wall at Pippins in Bream
44
Bream, Gloucestershire, GL15
  • Sleeps6
  • Bedrooms3
  • PetsNo

    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 €552

Last booked 1 hour ago
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An outdoor patio area with a round metal table and four chairs a fire pit and a small wooden storage box next to a wooden and stone building at The Comfy Cow in Llansoy near Raglan
22
Llansoy near Raglan, Monmouthshire, NP16
  • Sleeps2
  • Bedrooms1
  • PetsNo

    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 €506

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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 €962

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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 €1066

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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 €1397

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A covered outdoor patio area with stone flooring glass sliding doors and outdoor furniture at Hidden Well in Aust
45
Aust, Gloucestershire, BS35
  • Sleeps10
  • Bedrooms3
  • PetsNo

    4.8

    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 €1517

Last booked 2 days 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 €580

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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 €698

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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 €505

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A blue front door with a wreath and stacked firewood outside next to a potted plant and a stone bench at Lilly Cottage in Whitecroft Royal Forest of Dean
11
Whitecroft, Royal Forest of Dean, Gloucestershire, GL15
  • Sleeps2
  • Bedrooms1
  • PetsNo

    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 €636

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An outdoor tiled patio area with a black table and four chairs and a seating area near a white building at The Fountain Lodge in Parkend
35
Parkend, Gloucestershire, GL15
  • Sleeps4
  • Bedrooms2
  • PetsNo

    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 €533

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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 €525

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A living room with two black leather sofas a wooden chest coffee table and a wall mounted tv at Pool House The Narth near Trellech
33
The Narth near Trellech, Monmouthshire, NP25
  • Sleeps4
  • Bedrooms2
  • PetsYes

    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 €420

Last booked 3 days ago
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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 €656

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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 €525

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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 €395

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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 €513

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A wooden barn style building with a fenced grassy yard and a gravel driveway at Top Lodge in Llanvair-Discoed near Penhow
31
Llanvair-Discoed near Penhow, Monmouthshire, NP16
  • Sleeps4
  • Bedrooms2
  • PetsYes

    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

7 nights from €562

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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.