Rent Luxury Holiday Cottages in Chepstow

We selected the 832 homes worth renting in this location

Who's coming along?

Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

An extra fee may apply

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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 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.

Farm Fresh Living

Farm Fresh Living

  • 2 guests

  • 1 bedrooms

Boughspring, Chepstow

With sweeping countryside views and a hot tub perfectly positioned for starlit soaks, this peaceful retreat is all about slowing down. Ideal for two, and surrounded by fields and footpaths, this shepherd's hut sits in the heart of a working dairy farm in the Wye Valley, just fifteen minutes from Chepstow.

Rustic Luxe Retreat

Rustic Luxe Retreat

  • 6 guests

  • 3 bedrooms

Boughspring, Chepstow

Tucked into the hills near Chepstow and surrounded by a working dairy farm, this countryside escape blends rustic charm with easygoing luxury. Made up of a cosy shepherd's hut and an elegant farmhouse, it’s a thoughtful setup for families or friends.


We selected the top 3% holiday homes in Chepstow Cottages

Explore the 832 most perfect homes in our collection

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Most popular homes in Chepstow

The Druid's Hut

The Druid's Hut

  • 2 guests

  • 1 bedrooms

Devauden, Chepstow

Wild Boar & Trout Pond

Wild Boar & Trout Pond

  • 6 guests

  • 3 bedrooms

Aylburton, Lydney

Knights of the Round

Knights of the Round

  • 14 guests

  • 5 bedrooms

Caldicot, Wales

Wye Valley View

Wye Valley View

  • 6 guests

  • 3 bedrooms

Whitebrook, Monmouth

Forests & Fields

Forests & Fields

  • 6 guests

  • 3 bedrooms

Aylburton, Lydney

Gloucestershire Gaze

Gloucestershire Gaze

  • 2 guests

  • 1 bedrooms

Tidenham, Gloucestershire

Haybales & Horses

Haybales & Horses

  • 6 guests

  • 3 bedrooms

Mitchel Troy, Monmouth

Cider House Rules

Cider House Rules

  • 2 guests

  • 1 bedrooms

Hereford, Herefordshire

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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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