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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
4.89 out of 5 average rating, 154 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
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
4.88 out of 5 average rating, 522 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
Cottage
4.91 out of 5 average rating, 114 reviews

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, 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. It is a 2 minute walk to the village shop, garage & new coffee shop. The village pub is closed at the moment, there are 3 other good food pubs each just over 2 miles away.

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
5 out of 5 average rating, 352 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 spacious, pet-friendly garden is shown, featuring a lush green lawn surrounded by blooming bluebells and trees. A gravel path leads to a small shed and a seating area is visible, all under a clear blue sky with wispy clouds.
Cottage
4.97 out of 5 average rating, 102 reviews

Spacious cottage, sunny garden, stroll to town

Vauxhall Cottage is a charming home-from-home, ideal for families & friends, yet cosy for couples. The spacious layout offers social areas & quiet nooks, with 4 comfy bedrooms, large kitchen & lounge, sunroom & an enclosed, dog-friendly garden with patio & BBQ. The modernised 1790s Welsh cottage is a short stroll to Chepstow’s historic centre, Castle & riverside, ideal for the racecourse, & to explore the Forest of Dean, Wye Valley & beyond, with easy connections to Cardiff, Bristol & M4/M5.

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
4.97 out of 5 average rating, 198 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 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
4.99 out of 5 average rating, 271 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 stone cottage is featured with a modern roof and large windows, allowing natural light to fill the interior. A charming fountain and manicured garden surround the entrance, with outdoor seating visible for relaxation. The structure is harmoniously integrated into the landscape.
Cottage
4.98 out of 5 average rating, 301 reviews

Elm Park Barn, Chewton Keynsham, BS31 2SS

Nestled between the popular cities of Bristol and Bath, stunning views with exclusive use hot tub & large indoor heated swimming pool. 3 charming outdoor seating areas. Easy access to Bath and Bristol 'Park and Rides'. TVs in bedrooms, 65" lounge smart TV. WIFI, Bluetooth Boom Box. dishwasher, washing machine, and microwave. Not suitable for children under 18 or pets. Car essential. The base price is for 2 people. Extra guests 3 and 4 pay £65 per night per person.

Top guest favourite
An inviting dining area features a light-colored wooden table set with tableware, complemented by a cozy yellow sofa. A decorative wall piece and a flat-screen TV enhance the rustic charm of the stone interior, while a soft light illuminates the space through an arched doorway.
Cottage
4.97 out of 5 average rating, 178 reviews

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.

Top guest favourite
The entrance features a wooden door with a diamond-shaped window, framed by large glass panels that allow natural light to enter. Surrounding the entryway are lush green plants and ferns, enhancing the rustic charm of the stone cottage.
Cottage
5 out of 5 average rating, 105 reviews

Birch Cottage with woodland sauna

Birch Cottage is a charming 3-bedroom stone cottage with a secluded woodland sauna cabin and views across the Wye Valley countryside. It is located on Offas Dyke footpath on a very quiet road, so is great for anyone looking to explore the network of Wye Valley footpaths. Monmouth, Forest of Dean, Bristol, Bath and Cardiff are close enough for day visits. Whatever season you prefer, it's a wonderful place to recharge your batteries and connect with nature.

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
4.89 out of 5 average rating, 483 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.

Guest favourite
The exterior of a historic cottage is displayed, featuring a whitewashed facade with black window frames and a central door. Flower boxes are visible under the windows, while ivy is seen climbing the adjacent building, adding charm to the scene. A lamppost stands nearby.
Cottage
4.92 out of 5 average rating, 126 reviews

Historic cottage opposite Chepstow Castle

Directly opposite the castle, this cottage is in the perfect location for exploring Chepstow and its surrounding areas. The cottage dates back to the 17th century, but has been freshly modernised. Expect a homely yet luxurious stay. Chepstow itself is a historic town, packed with lovely restaurants, pubs, cafés and shops. Our house guide will give you plenty of recommendations to make the most of the area.

Popular amenities for cottage rentals in Chepstow

Quick stats about cottage rentals in Chepstow

  • Nightly prices starting at

    Chepstow holiday rentals start at £66 per night before taxes and fees

  • Verified guest reviews

    Over 1,280 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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