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Cottage vacation rentals in Chepstow

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Top-rated cottage rentals in Chepstow

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Guest favorite
A spacious garden showcases blooming flowers, including tulips and bluebells, framed by a stone wall. Lush greenery fills the background, featuring tall trees and scattered shrubs. A decorative stone feature stands centrally, surrounded by vibrant plant life under a clear blue sky.
Cottage in Tidenham Chase
4.89 out of 5 average rating, 147 reviews

Goldcrest-Lodge-Forest-of-Dean

Take it easy at this unique and tranquil getaway. Set in the Wye Valley, an area of outstanding natural beauty. You can walk/cycle for miles without touching a road. Collect eggs, milk and delicious ice cream from the farm next door Tintern Abbey with its pubs and restaurants is a walk away (an hour); the races, music at the Castle, Clearwell Caves, Puzzlewood, steam train.. and more. Travelling with friends/family? Check our other listing within the same grounds airbnb.com/h/wyevalleydairy-uk

Top guest favorite
A cozy living area is presented, featuring a blue sofa paired with a yellow armchair adorned with a decorative pillow. A coffee table sits in front, with a wood-burning stove on one side. Natural light filters through a multi-pane window, framed by dark curtains.
Cottage in Chepstow
4.87 out of 5 average rating, 493 reviews

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.

Guest favorite
A charming stone cottage is set against a backdrop of lush greenery. The two-story structure features large windows, showcasing natural light. The surrounding area is accented by trees and plants, with a slight incline leading to the entrance.
Cottage in Monmouthshire
4.92 out of 5 average rating, 128 reviews

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.

Top guest favorite
A charming stone cottage is illuminated softly at dusk, showcasing a welcoming entrance. A small patio area features light wooden furniture and a large umbrella, surrounded by lush greenery and blooming flowers in planters, evoking a peaceful outdoor space.
Cottage in Tarrington
5 out of 5 average rating, 292 reviews

Countryside Cidermaker's Cottage

A characterful and lovingly converted 18th century cider makers cottage in the heart of the Herefordshire countryside. The interior is welcoming, cosy and unique. A mix of modern and quirky. Only 7.5 miles from the historic city of Hereford and the market town of Ledbury. An idyllic countryside retreat. Perfect for foodies, walkers, cyclists or a bolthole for getting away from it all. We are only 1.5 hours from Birmingham and Bristol airports and 2 3/4 hours drive from London Heathrow.

Top guest favorite
A feature arched window frames panoramic views of rolling hills and fields, with sunlight illuminating the stone wall and wooden shutters. A vase of fresh flowers sits on a round table, enhancing the inviting atmosphere of the open living space.
Cottage in Saint Briavels
5 out of 5 average rating, 338 reviews

Wye Valley Escape. Romantic Loft on 40-Acre Estate

Romantic luxury loft for two on a 40-acre private estate in the Wye Valley National Landscape. Perfect for honeymooners, stargazers, proposals, anniversaries, or milestone moments. Enjoy panoramic Mork Valley views through the feature arched window, vaulted oak beams, and a cozy fire pit (logs & marshmallows incl.). Includes a generous welcome hamper and exclusive access to our dark skies, meadows, stream, and woodland. A peaceful, magical retreat with high-end, curated experiences available.

Top guest favorite
A charming cottage with a brick exterior showcases climbing roses and vibrant flowers along its walls. Graceful windows are complemented by a small path leading to a well-maintained lawn, enhancing the tranquil setting surrounded by greenery.
Cottage in Wotton-under-Edge
5 out of 5 average rating, 229 reviews

Peaceful South facing cottage in Cotswolds. UK,

South facing, quiet, cottage with exceptional views set in valley of "Outstanding natural beauty" close by "The Cotswold Way" and miles of wonderful walks from the doorstep. Light filled rooms are decorated with original paintings and textiles. There are 2 computer chairs, a good table for laptops & business connection wi fi in the cottage. Relax by the wood burning stove, sleep on a super king size antique brass bed. Private south facing small terrace & lawn which cannot be overlooked.

Top guest favorite
A quaint stone cottage is framed by lush greenery, featuring a large window that invites natural light inside. The well-maintained lawn includes neatly trimmed hedges and a comfortable seating area, creating a serene outdoor environment.
Cottage in Monmouthshire
4.97 out of 5 average rating, 190 reviews

Peaceful Stone Cottage among fabulous gardens

The Garden House is a peaceful stone cottage set in the historic gardens of High Glanau Manor, the home of H. Avray Tipping (1855-1933) the Architectural Editor of Country Life Magazine from 1907. High Glanau Manor is an important Arts & Crafts house set in 12 acres of gardens designed in 1922. The gardens retain many original features including formal terraces, octagonal pool, glasshouse, pergola and 100 ft long double herbaceous borders. There are spectacular views to the Brecon Beacons

Top guest favorite
A tranquil outdoor patio area is surrounded by vibrant red flowers and lush greenery. A round table is set with a potted plant, complemented by several chairs arranged around it. The blue sky provides a bright and inviting backdrop for relaxation.
Cottage in Frome Vale
4.97 out of 5 average rating, 406 reviews

Beautiful Cider House Village Getaway Sleeps 4

The Cider House is a spacious and comfortable home opposite the Village Green in Cromhall, near to Wotton-under-Edge on the southern fringe of the Cotswolds in Gloucestershire. The village is conveniently located for the M5, with J14 approx. 10 mins by car, and the A38 a similar distance. Easy access to local market towns of Thornbury and Wotton-under-Edge, as well as to Bristol and Bath. The barn is next door to our home but entirely self-contained and private with parking for two cars.

Top guest favorite
The cottage is set amongst lush greenery, featuring a spacious lawn and a well-kept garden. Its exterior is painted white, with large windows and a welcoming entrance. A backdrop of trees adds to the tranquil atmosphere, creating a serene retreat in the countryside.
Cottage in Brockweir
4.99 out of 5 average rating, 254 reviews

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.

Top guest favorite
The cottage features a charming stone exterior with a sloped roof, surrounded by well-maintained gardens. A classic lamppost is positioned in the foreground, and a decorative wooden wheel adds rustic appeal. The private driveway exhibits a spacious brick pattern, inviting guests to approach the entrance.
Cottage in South Gloucestershire
4.96 out of 5 average rating, 156 reviews

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.

Guest favorite
The exterior of Wern Farm Cottage is showcased, featuring a stone facade partially covered by greenery. The structure is surrounded by a lush lawn and trees, offering a natural, serene setting. A window reflects the outdoor greenery, enhancing the inviting atmosphere.
Cottage in Monmouthshire
4.91 out of 5 average rating, 343 reviews

Luxurious spacious cottage with awesome views !

With commanding views over Monmouth, the Wye Valley and beyond, Wern Farm Cottage is a cosy but spacious recluse ideally situated for all that Monmouthshire has to offer. Light, airy and welcoming with zip and link beds. We can accommodate 2-4 flexible to your needs. We are in a great spot for the Forest of Dean, the Brecon Beacons, Bike Park Wales, Cannop Cycle Centre and the Offa’s Dyke Path. There are lovely walks right from the door and so much to do nearby!

Guest favorite
The cottage's stone façade is highlighted by warm wooden accents, surrounded by a garden featuring vibrant daffodils in bloom. A rustic wall made of local stone outlines the property, complementing the natural landscape in the background. Sunlight casts gentle shadows across the scene.
Cottage in Llandogo
4.92 out of 5 average rating, 256 reviews

Cosy Cottage | 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.

Popular amenities for Chepstow cottage rentals

Quick stats about cottage rentals in Chepstow

  • Nightly prices starting at

    Chepstow vacation rentals start at ﺩ.ﺇ367 per night before taxes and fees

  • Verified guest reviews

    Over 1,190 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chepstow rentals

  • 4.9 Average rating

    Chepstow stays are highly rated by guests—averaging 4.9 out of 5!

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