Holiday Cottages in Chepstow

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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
  • A house with a gravel driveway and front garden at 3 bed property
    58
    Raglan, South Wales & Pembrokeshire
    • Sleeps5
    • Bedrooms3
    • Pet FriendlyYes

      4.9★

      Outstanding

    • Coast & Country Holidays rating

    Tawny Cottage is a charming cottage in Raglan, Monmouthshire, boasting a woodburning stove, countryside views and five acres of woodland to explore. (Ref. 1183265)

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

    7 nights from From €901

    Book now
  • A wooden barn style building with a fenced grassy yard and a gravel driveway at Top Lodge in Llanvair-Discoed near Penhow
    44
    Llanvair-Discoed near Penhow, South Wales & Pembrokeshire
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.6★

      Outstanding

    • Coast & Country Holidays rating

    A beautiful oak-clad lodge resting in Llanvair-Discoed, Monmouthshire. (Ref. 1112486)

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

    7 nights from From €478

    Book now
  • A garden with a stone patio and seating at 1 bed property in Usk
    27
    Raglan, South Wales & Pembrokeshire
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyYes

      5.0★

      Perfect

    • Coast & Country Holidays rating

    Walnut Cottage is a romantic cottage in Raglan, Monmouthshire, featuring a woodburning stove, countryside views and access to five acres of woodland. (Ref. 1183268)

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

    7 nights from From €540

    Last booked yesterday
    Book now
  • 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
    35
    The Narth near Trellech, South Wales & Pembrokeshire
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.7★

      Outstanding

    • Coast & Country Holidays rating

    A lovely, semi-detached cottage located in the charming village of The Narth near Trellech in Monmouthshire. (Ref. 1025887)

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

    7 nights from From €402

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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
    22
    Penhow, South Wales & Pembrokeshire
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.7★

      Outstanding

    • Coast & Country Holidays rating

    A stunning detached lodge perched in Llanvair-Discoed, Monmouthshire. (Ref. 1117998)

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

    7 nights from From €477

    Book now
  • 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, South Wales & Pembrokeshire
    • Sleeps3
    • Bedrooms2
    • Pet FriendlyYes

      4.7★

      Outstanding

    • Coast & Country Holidays rating

    A cosy detached stone-built cottage in the village of Trellech. (Ref. 938052)

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

    7 nights from From €371

    Book now
  • A house with a garden and patio at Woods Cottage Kingcoed near Raglan
    34
    Kingcoed near Raglan, South Wales & Pembrokeshire
    • Sleeps5
    • Bedrooms3
    • Pet FriendlyYes

      4.5★

      Outstanding

    • Coast & Country Holidays 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. (Ref. 1152870)

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

    7 nights from From €623

    Last booked yesterday
    Book now
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Steeped in history and surrounded by stunning natural landscapes of Monmouthshire, holiday cottages in Chepstow offer a blend of historical exploration and outdoor adventures.

Staying in a cottage in Chepstow allows you to wander its historic streets, visit the impressive Chepstow Castle, and enjoy scenic walks along the Wye Valley and Offa’s Dyke Path.

Why Choose Holiday Cottages in Chepstow?

A Chepstow self-catering cottage is perfect for those looking to explore both history and nature while enjoying a peaceful retreat. 

As one of the gateways to Wales, this charming market town boasts rich heritage, with one of the oldest surviving stone castles in Britain, Chepstow Castle stands proud above the River Wye. 

Beyond its historic sites, Chepstow is a fantastic base for outdoor lovers with the Wye Valley Area of Outstanding Natural Beauty, offering stunning walking trails, rolling hills and scenic riverbanks. 

With easy access to both Welsh and English attractions, a stay in a holiday cottage in Chepstow ensures a mix of relaxation, exploration, and adventure. 

Places to Visit from Chepstow Self-Catering Cottages

Staying in a self-catering cottage in Chepstow puts you in the perfect location to explore some of the most stunning and historic sites in South Wales and the West of England.  

A must-visit is the stunning Chepstow Castle, a breathtaking Norman fortress offering panoramic views and centuries of history to uncover. 

For outdoor adventures, explore the Wye Valley Area of Outstanding Natural Beauty, known for its scenic walking trails and dramatic river landscapes—you could easily spend a full day here.

Another nearby area is the Forest of Dean, where you can enjoy activities ranging from hiking and cycling to canoeing on the River Wye.

Meanwhile, the vibrant city of Bristol is just across the Severn Bridge, featuring a host of attractions such as the SS Great Britain and a variety of museums and shops.

Whatever you seek, a holiday cottage in Chepstow provides the perfect base for an unforgettable getaway.

Other Popular Destinations near Cottages in Chepstow: 

Cardiff 

Machynlleth 

Swansea 

Types of Holidays in Wales 

Secure your next countryside break today with a holiday cottage in Chepstow!

If you're interested in exploring other options, a wide range of alternatives awaits, including coastal cottages (as well as plenty of remote options), sea view cottages, cottages with hot tubs, detached cottages, glamping pods, shepherd’s huts, large cottages, cottages with stunning views, mountain cottages and lots of cottages for romantic getaways too. 

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