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Holiday Cottages in Chepstow

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Your search returned 25 cottages.

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  • The Comfy Cow

    Llansoy near Raglan, South Wales & Pembrokeshire
    • Sleeps2
    • Bedrooms1
    • PetsNo
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    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)

    12 customer reviews

    7 nights from £347

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  • The Elms

    Shirenewton near Chepstow, South Wales & Pembrokeshire
    • Sleeps6
    • Bedrooms3
    • PetsYes
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    A large, detached property resting in over 40 acres of land near Chepstow. Pet-friendly. Woodburning stove. WiFi. Newport 18 miles. (Ref. 1050456)

    6 customer reviews

    7 nights from £443

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  • Golden Valley Barn

    Oldbury-On-Severn, Gloucestershire
    • Sleeps4
    • Bedrooms2
    • PetsNo
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    A charming detached barn conversion, close to Oldbury-on-Severn in Gloucestershire. Exposed beams. En-suite. Ground-floor bedroom. (Ref. 1011610)

    9 customer reviews

    7 nights from £374

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  • The Pound

    Trellech near Monmouth, South Wales & Pembrokeshire
    • Sleeps3
    • Bedrooms2
    • PetsYes
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    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)

    5 customer reviews

    7 nights from £295

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  • Twixt Cottage

    Bream, Gloucestershire
    • Sleeps4
    • Bedrooms2
    • PetsYes
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    This delightful country cottage is located in Bream, Gloucestershire. Pet-friendly. Woodburner. Coleford 3 miles; Lydney 4 miles. (Ref. 998749)

    15 customer reviews

    7 nights from £307

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  • Lilly Cottage

    Whitecroft, Royal Forest of Dean, Gloucestershire
    • Sleeps2
    • Bedrooms1
    • PetsNo
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    A beautifully presented romantic cottage in the heart of Whitcroft, Gloucestershire. Edge of forest. Hot tub. Woodburner. Monmouth 7 miles. (Ref. 991699)

    10 customer reviews

    7 nights from £420

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  • The Old Baptist Chapel

    Penallt, Wye Valley, South Wales & Pembrokeshire
    • Sleeps4
    • Bedrooms2
    • PetsYes
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    A superb chapel conversion in village of Penallt. Character features, woodburning stove, en-suite bedrooms. Award-winning pub within walking distance. Monmouth 5 miles. (Ref. 22484)

    12 customer reviews

    7 nights from £438

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  • The Granary

    St Briavels, Gloucestershire
    • Sleeps4
    • Bedrooms2
    • PetsNo
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    A beautifully presented cottage in the lovely village of St. Briavels near Lydney in Gloucestershire. Stunning gardens. Conservatory. TV. Upside down layout. Pub 5 mins walk. St. Briavels Castle. (Ref. 985313)

    4 customer reviews

    7 nights from £330

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  • Carriage Apartment

    Lydney, Gloucestershire
    • Sleeps4
    • Bedrooms2
    • PetsYes
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    Tastefully-furnished contemporary apartment in listed coach house above the town of Lydney, with glorious views towards the River Severn. Lydney 0.7 miles. (Ref. 924554)

    3 customer reviews

    7 nights from £372

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  • Little Millend

    Coleford, Gloucestershire
    • Sleeps6
    • Bedrooms3
    • PetsYes
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    Lovely, detached, stone cottage on the edge of the Forest of Dean. Fantastic decked area and hot tub from where you enjoy views stretching off into the distance. (Ref. 988966)

    39 customer reviews

    7 nights from £774

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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!

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.