Your search returned 7 cottages.
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- Sleeps8
- Bedrooms3
- PetsNo
An idyllic, characterful cottage near Chepstow, Monmouthshire. (Ref. 1118276)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from £732
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- Sleeps2
- Bedrooms1
- PetsNo
A fabulous converted bull pen situated in the rural countryside of Llansoy near Raglan. (Ref. 1010598)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
7 nights from £420
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- Sleeps4
- Bedrooms2
- PetsYes
A stunning detached lodge perched in Llanvair-Discoed, Monmouthshire. (Ref. 1117998)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Hot Tub
- Dishwasher
- Washing machine
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10% off - Sun 1st Jun to 9th Jun 2025
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10% off - Fri 27th Jun to 5th Jul 2025
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10% off - Sat 5th Jul to 13th Jul 2025
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10% off - Sun 13th Jul to 21st Jul 2025
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10% off - Mon 21st Jul to 29th Jul 2025
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10% off - Tue 29th Jul to 6th Aug 2025
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5% off - Wed 6th Aug to 15th Aug 2025
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10% off - Fri 15th Aug to 30th Aug 2025
7 nights from £431
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- Sleeps4
- Bedrooms2
- PetsYes
A lovely, semi-detached cottage located in the charming village of The Narth near Trellech in Monmouthshire. (Ref. 1025887)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
7 nights from £354
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- Sleeps4
- Bedrooms2
- PetsYes
A beautiful oak-clad lodge resting in Llanvair-Discoed, Monmouthshire. (Ref. 1112486)
- Wi-fi
- Off-road parking
- Hot Tub
- Dishwasher
- Washing machine
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5% off - Fri 25th Apr to 3rd May 2025
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5% off - Fri 9th May to 17th May 2025
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5% off - Sat 17th May to 25th May 2025
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5% off - Sun 25th May to 1st Jun 2025
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5% off - Sun 1st Jun to 9th Jun 2025
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5% off - Mon 9th Jun to 17th Jun 2025
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5% off - Tue 17th Jun to 25th Jun 2025
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10% off - Fri 1st Aug to 16th Aug 2025
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5% off - Sat 16th Aug to 24th Aug 2025
7 nights from £460
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- Sleeps3
- Bedrooms2
- PetsYes
A cosy detached stone-built cottage in the village of Trellech. (Ref. 938052)
- Wi-fi
- Off-road parking
- Washing machine
- Baby-friendly
7 nights from £333
Secure your holiday with a 30% deposit* Book now -
- Sleeps4
- Bedrooms2
- PetsNo
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. (Ref. 13460)
- Wi-fi
- Dishwasher
- Washing machine
7 nights from £458
Secure your holiday with a 30% deposit* Book now
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:
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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