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Cottage holiday rentals in Chepstow

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Top-rated cottage rentals in Chepstow

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Guest favourite
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, 149 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 favourite
The exterior of Pineapple Cottage is shown, featuring a gray facade and a teal front door. Two potted plants sit beside the doorway. A cobbled street leads upward, lined with traditional buildings and a lantern light adding a touch of character to the scene.
Cottage in Chepstow
4.87 out of 5 average rating, 507 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 favourite
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, 129 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 favourite
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, 341 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 favourite
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, 191 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 favourite
The entrance to the Cider House is framed by lush greenery, featuring a blue door under a warm glow from an exterior light. The stone exterior reflects the building's history, while nearby windows offer glimpses of the interior. A gentle slope leads to the front door.
Cottage in Frome Vale
4.97 out of 5 average rating, 419 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 favourite
A shaded outdoor gazebo features a large table adorned with a bright tablecloth. Surrounding foliage enhances the garden's natural beauty, while wooden folding chairs provide comfortable seating. Potted plants, including colorful flowers, are placed at the edges, creating a welcoming outdoor space.
Cottage in Brockweir
4.99 out of 5 average rating, 261 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 favourite
A gravel driveway leads to the entrance of a charming cottage made of stone. The cottage features a wooden garage door and is surrounded by lush greenery, with trees framing the view. Soft clouds are visible in the sky above.
Cottage in Alvington
4.99 out of 5 average rating, 118 reviews

Tranquil cottage Forest of Dean

Wake up to the sound of bird song and enjoy the serenity of this charming dog friendly cottage nestled in Alvington. Explore The Forest of Dean with its countless walking and cycling trails, where there is the opportunity to see wild boar, pine martens and deer. Perfectly positioned to discover Tintern Abbey, FOD Steam Railway, Symonds Yat and the stunning Wye valley. Great pubs and eateries. This is a retreat for nature lovers and adventurers rather than shoppers. Come and enjoy.

Top Guest favourite
An aerial view captures the serene landscape surrounding the property. The detached coach house and main residence are positioned near a winding road, with green fields stretching into the distance. Trees and hedges frame the area, contributing to the rural setting.
Cottage in Slimbridge
4.98 out of 5 average rating, 446 reviews

The Coach House

Beautiful cosy detached coach house, off-road parking. Located in semi rural village on no through road. Open plan kitchenette and lounge downstairs, upstairs comprises of bedroom with kingsize bed, toilet and separate shower room. Ideal for country walks and conveniently located for many nearby attractions including Slimbridge wildfowl wetlands centre, Berkeley Castle and short drive to Bristol or Cheltenham Racecourse. Shared outside space including car parking and garden.

Guest favourite
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, 348 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 favourite
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, 259 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.

Guest favourite
A bright kitchen area features wooden flooring and natural light from a window. A wooden dining table with four chairs is present, complemented by a potted plant in the corner. The kitchen is equipped with modern appliances and white cabinetry.
Cottage in Monmouthshire
4.89 out of 5 average rating, 471 reviews

Carpenters Cottage - Central Chepstow with parking

Carpenters Cottage is a quaint cosy one bedroom cottage at the bottom of Chepstow Town. It’s 2 minutes walk to the castle, town centre or the pubs on the river wye. The cottage is fully equipped with all your necessities for a wonderful home from home stay. Recently completely refurbished to a high standard it offers comfort, style and privacy with a 4* luxury finish. We hope you enjoy your stay and want to come again.

Popular amenities for Chepstow cottage rentals

Quick stats about cottage rentals in Chepstow

  • Nightly prices starting at

    Chepstow holiday rentals start at $126 AUD per night before taxes and fees

  • Verified guest reviews

    Over 1,230 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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