Rent Luxury Holiday Cottages in Chepstow

We selected the 824 homes worth renting in this location

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Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

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Home spotlights in Chepstow

Farmers Daughter

Farmers Daughter

  • 4 guests

  • 2 bedrooms

Boughspring, Chepstow

With breathtaking panoramas from every vantage point, this home is a gem. You'll be able to enjoy the views from the private hot tub and garden – although our favourite is the glimpses of the River Severn and Old Severn Bridge from the main bedroom.

The Druid's Hut

The Druid's Hut

  • 2 guests

  • 1 bedrooms

Devauden, Chepstow

These luxurious shepherd’s huts are an excellent choice for a romantic retreat. This quirky home can be found in a secluded meadow on the edge of a natural wood, close to the ancient settlement of Penterry.

The Cider Barn

The Cider Barn

  • 10 guests

  • 5 bedrooms

Pilning, South Gloucestershire

With far-reaching countryside views, this stylish Gloucestershire barn conversion is the perfect retreat for families and friends. The large private garden is a great place to relax with its hot tub, paved patio complete with barbecue and alfresco dining table.

Wild Boar & Trout Pond

Wild Boar & Trout Pond

  • 6 guests

  • 3 bedrooms

Aylburton, Lydney

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We selected the top 3% holiday homes in Chepstow Cottages

Explore the 824 most perfect homes in our collection

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Most popular homes in Chepstow

Knights of the Round

Knights of the Round

  • 14 guests

  • 5 bedrooms

Caldicot, Wales

Forests & Fields

Forests & Fields

  • 6 guests

  • 3 bedrooms

Aylburton, Lydney

Wye Valley View

Wye Valley View

  • 6 guests

  • 3 bedrooms

Whitebrook, Monmouth

Gloucestershire Gaze

Gloucestershire Gaze

  • 2 guests

  • 1 bedrooms

Tidenham, Gloucestershire

Haybales & Horses

Haybales & Horses

  • 6 guests

  • 3 bedrooms

Mitchel Troy, Monmouth

High Above The Whole Scene

High Above The Whole Scene

  • 2 guests

  • 1 bedrooms

Colerne, Wiltshire

Sugar & Lime

Sugar & Lime

  • 4 guests

  • 2 bedrooms

Rodmarton, Cirencester

Serenity in the Black Mountains

Serenity in the Black Mountains

  • 27 guests

  • 9 bedrooms

Llanigon, Hereford

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Frequently asked questions

Discover our curated collection of luxury holiday Cottages in Chepstow. We painstakingly review all homes available in a destination and accept only the top 3% to ensure quality our guests can trust. Each of the Chepstow Cottages in our collection comes fully furnished with essential bathroom toiletries, expertly-equipped kitchens and all linens included. Book your dream stay today and should you need some help, our friendly team of experts are on hand to help plan your perfect Cottage break.

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