Cottage holiday rentals in Chepstow

Pineapple Cottage - Chepstow Town Centre (Wales)

17th Century cottage in the heart of Chepstow, close to Offa's Dyke & the Wye Valley. Tucked down a little cobbled street in the town centre, it’s a small but perfectly formed cottage ideal for a couple or a young family. There’s a secret door leading to the second bedroom, where you’ll even get a glimpse of Chepstow Castle from the window. It’s an ideal base for weddings at St Tewdrics (we’ve even hosted the bride and groom!) or for walking and cycling in the Forest of Dean and Wye Valley.

The Old Coach House at Tintern, the Wye Valley

The old coach House is a few minutes walk from the centre of Tintern on the banks of the river Wye, where you'll find the famous abbey, as well as places to eat and drink, and shops selling local crafts. The Wye Valley Walk passes the house, and the hourly bus between Chepstow and Monmouth stops just metres away. Staying at the historic Old Coach House in Tintern, you'll experience the unique charm of an early 1800s Welsh cottage, while enjoying modern comforts in a stylish and homely setting.

Country Cottage 25% Weekly Discount, Covered Patio

The Mews House is a homely, light & spacious character cottage in the village of Llanishen, Monmouthshire, between the Wye & Usk Valleys, both AONB areas. There is a variety of attractions including walks from the property and in the local area, castles, Tintern Abbey, the River Wye, Roman Caerleon, horse riding, cycling & golf. There is a good food pub & shop only 3 minutes walk away (temporarily closed 16/8/25) . The two super king beds can both be set out as twin beds to suit your needs.

3 bedroom, peaceful, secluded, & large garden

Hidden away on the edge of the ancient Forest of Dean, in the beautiful Wye Valley, with a large secluded garden, accessed by a mile long, narrow, single track lane, hanging with ferns in summer. It's is a fabulous place for walkers and town escapees. Once a woodman’s cottage, with a cosy, spacious interior, fully equipped kitchen, log burner, very comfortable beds, all you need for a relaxing break. Not suitable for young children 1-12, the large garden has a pond and steep terracing.

Set in AONB & 40 Acres of Private Countryside

Perfectly situated to explore all the Wye Valley and Forest of Dean has to offer, The Apple Loft is an idyllic getaway popular with honeymooners, walkers, cyclists and those just wishing to escape the hustle and bustle of everyday life. With panoramic views across Mork Valley, guests can walk our grassy tracks, explore the old lime kilns, picnic in our fields, say ‘hello’ to the pet sheep and enjoy the sights and sounds of nature, stars and sunsets in this magical and relaxing retreat.

Scenic 1-bedroom cottage with beautiful views

A self-contained tranquil cottage in a private gated residence within a quiet hamlet bordering Tortworth Estate fields and beautiful views. Sensational country walks and cycling straight from the property, but only 3 minutes from the M5 for maximum accessibility to the local areas of Bath, Bristol, Chepstow and Gloucester. NB the cottage is beside our house with its own patio and garden. You share our gated driveway for parking. Please feel free to make a pre-booking enquiry.

Cotswolds Romantic Getaway in Luxury Barn

The Barn at Church View is a unique luxury conversion of a 200 year old stone former calving barn in The Cotswolds, near the maket towns of Thornbury and Wotton-under-Edge. Its privileged countryside location is within easy reach of the vibrant cities of Bristol, Bath and Gloucester offering an abundance of things to do. The recently renovated barn is a tranquil private space away from noisy roads, the perfect setting for your next holiday or romantic getaway.

Olli's Cottage-Terrace &Jacuzzi

Olli's cottage is situated in one of Bristol picturesque suburds, newly refurbished 700sq Ft/70 Sqm with private terrace and hot tub (3 days notice required/small extra charge). In close proximity to La Villa Olli: Swimming pool with waterfall, pool table & ping pong table (Small extra charge). Located near M4/M5, making travel to/from easy. Perfect for a couple getaway or a business trip in a tranquil environment within 5 minutes access to country pubs.

Peaceful Escape | Dog Friendly | Wye Valley

Mill Cottage is a delightful stone cottage situated on a private lane in the heart of a pretty village located on the River Wye. The original cottage is over 150 years old and was the home of the sawmill manager, who ran the nearby sawmill, which has long since disappeared. It is now a lovely holiday cottage, that sleeps two couples and one well-behaved dog. It overlooks a pretty church and is very conveniently located for the village pub.