Book Luxury Monthly Rentals in Chepstow

We selected the 1820 homes worth renting in this location

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Home spotlights in Chepstow

Gloucestershire Gaze

Gloucestershire Gaze

  • 2 guests

  • 1 bedrooms

Tidenham, Gloucestershire

Nestled in the grounds of the owner’s home, in the peaceful village of Stroat, this home is perfect for a couple’s getaway to the country. With far-reaching views from the private garden and a cosy hot tub, ideal for soaking tired muscles after a day exploring the great outdoors, this home ticks a lot of holiday boxes.

An Emerald Escape

An Emerald Escape

  • 4 guests

  • 2 bedrooms

Lydney, Gloucestershire

This comfortable apartment in Lydney is an excellent base for exploring the Forest of Dean and Gloucestershire. It’s on the edge of the Cotswolds Area of Outstanding Natural Beauty, too – charming villages and stunning countryside await.

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 Burrow

The Burrow

  • 2 guests

  • 1 bedrooms

Brewham, Somerset

A lot of time and thought has been put into converting the historic chapel that is now The Burrow. Nestled in a tranquil spot of countryside surrounded by rolling hills, the space feels authentically rustic but still comfortable and elegant.


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

Explore the 1820 most perfect homes in our collection

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Most popular homes in Chepstow

Rustic Luxe Retreat

Rustic Luxe Retreat

  • 6 guests

  • 3 bedrooms

Boughspring, Chepstow

The Cotswold Idyll

The Cotswold Idyll

  • 6 guests

  • 3 bedrooms

Lower Slaughter, Cheltenham

Forest King

Forest King

  • 14 guests

  • 6 bedrooms

West Dean, Gloucestershire

Green Village

Green Village

  • 10 guests

  • 3 bedrooms

Pilning, South Gloucestershire

Shakespearean Elegance

Shakespearean Elegance

  • 2 guests

  • 1 bedrooms

Bidford-on-Avon, Alcester

The Vintage Farmhouse

The Vintage Farmhouse

  • 12 guests

  • 6 bedrooms

Thornbury, Herefordshire

The Druid's Hut

The Druid's Hut

  • 2 guests

  • 1 bedrooms

Devauden, Chepstow

Farmers Daughter

Farmers Daughter

  • 4 guests

  • 2 bedrooms

Boughspring, Chepstow

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Frequently asked questions

Discover the ultimate collection of luxury Monthly Rentals in Chepstow, and say goodbye to all your travel troubles. Here at Plum Guide, it is our promise that each and every home in our range is in the top 3% of homes in its location, so there is no doubting the consistent quality we are able to offer. Secure your extended or short stay today and enjoy the trip of a lifetime in your fully furnished home, with every property on our site including all linens, essential bathroom toiletries, and a perfectly-equipped kitchen. Our meticulous home critics test everything from Wifi speed to a home's design, so you really can trust our judgement. Rent your perfect Chepstow Monthly Apartment today with the help of our team of experts, on standby 24/7 to assist you with absolutely anything.

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