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We selected the 1818 luxury monthly villas and homes worth renting in this location

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Home spotlights in Chepstow

The Memory Jar

The Memory Jar

  • 24 guests

  • 9 bedrooms

Hereford, Herefordshire

With the flexibility to sleep up to 24 people, this magical country house is all set up for special events, gatherings of friends and family, activity holidays and more. With views across the Wye Valley, it's set on five acres of pristine land and has nine bedrooms for you to choose between – either in the beautifully restored and extended 17th-Century farmhouse or the stunning new guest annexe.

The Robins & The Roses

The Robins & The Roses

  • 4 guests

  • 2 bedrooms

Stow-on-the-Wold, Gloucestershire

When you think of the Cotswolds, chances are you picture chocolate-box villages, cobbled lanes and that famous honey-coloured stone. Stow-on-the-Wold promises all that and more.

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.

Light of the Forest

Light of the Forest

  • 6 guests

  • 3 bedrooms

Aylburton, Lydney

Sitting peacefully on the edge of the Forest of Dean, this home provides the perfect setting for a refreshing retreat. Outside, you can enjoy the views while soaking in the hot tub (available for an additional fee).


We selected the top 3% holiday homes in Chepstow Self-Catering Apartments

Explore the 1818 most perfect homes in our collection

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Most popular homes in Chepstow

The Coaching House

The Coaching House

  • 8 guests

  • 3 bedrooms

Lacock, Chippenham

The Cotswold Cedar

The Cotswold Cedar

  • 4 guests

  • 1 bedrooms

Painswick, Stroud

Dovesong

Dovesong

  • 6 guests

  • 3 bedrooms

Weston Subedge (DET), Gloucestershire

A Glass And A Half

A Glass And A Half

  • 2 guests

  • 1 bedrooms

Llanfrynach, Brecon

The Heart of the Forest

The Heart of the Forest

  • 24 guests

  • 12 bedrooms

Aylburton, Lydney

Wye Valley View

Wye Valley View

  • 6 guests

  • 3 bedrooms

Whitebrook, Monmouth

Serenity in the Black Mountains

Serenity in the Black Mountains

  • 27 guests

  • 9 bedrooms

Llanigon, Hereford

Penny-Farthing

Penny-Farthing

  • 4 guests

  • 2 bedrooms

Malmesbury, Wiltshire

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Frequently asked questions

Book luxury Self-Catering Apartments in Chepstow, and enjoy a memorable stay for all the right reasons. We leave no stone unturned in our pursuit of the most remarkable homes, vetting everything from shower pressure to design aesthetic. Every home in our collection of luxury Chepstow Self-Catering Rentals comes fully furnished with a well-equipped kitchen, all linens, and essential bathroom toiletries included. And should you need any help in finding the perfect home, our friendly experts are always on hand to help.

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