Book Luxury Holiday Rentals in Chepstow

Award-winning homes from £98

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Home spotlights in Chepstow

Green Village

Green Village

  • 10 guests

  • 3 bedrooms

Pilning, South Gloucestershire

Close to Bristol for work or play yet nicely nestled in the countryside, this three-bedroom home is a peaceful place to relax within easy reach of the city. The bright, double-height living area offers plenty of room to cook, dine, and unwind, while the en-suite bedrooms are comfy and modern.

Dovesong

Dovesong

  • 6 guests

  • 3 bedrooms

Weston Subedge (DET), Gloucestershire

Private farmland surrounds this stunning converted barn, a traditional slice of countryside tranquillity. There's a delicate balance of modern grandeur and tasteful tradition here.

The Cotswold Way

The Cotswold Way

  • 5 guests

  • 3 bedrooms

Chipping Campden, Gloucestershire

There's something to satisfy everyone's wanderlust at this charming period cottage nestled right in the beating heart of Chipping Campden. This is your gateway to the best of the Cotswolds – Market Hall, The Spa at Cotswold House and Chipping Campden's bustling high street are all within walking distance.

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.


We selected the top 3% holiday homes in Chepstow Holiday Rentals

Explore the 1820 most perfect homes in our collection

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Most popular homes in Chepstow

Farmers Daughter

Farmers Daughter

  • 4 guests

  • 2 bedrooms

Boughspring, Chepstow

The Idyllic Retreat

The Idyllic Retreat

  • 14 guests

  • 7 bedrooms

Winford, North Somerset

Haybales & Horses

Haybales & Horses

  • 6 guests

  • 3 bedrooms

Mitchel Troy, Monmouth

The Cotswold Cedar

The Cotswold Cedar

  • 4 guests

  • 1 bedrooms

Painswick, Stroud

Shakespearean Elegance

Shakespearean Elegance

  • 2 guests

  • 1 bedrooms

Bidford-on-Avon, Alcester

Knights of the Round

Knights of the Round

  • 14 guests

  • 5 bedrooms

Caldicot, Wales

The Cider Barn

The Cider Barn

  • 10 guests

  • 5 bedrooms

Pilning, South Gloucestershire

Penny-Farthing

Penny-Farthing

  • 4 guests

  • 2 bedrooms

Malmesbury, Wiltshire

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Chepstow. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that Chepstow has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

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