Cottage vacation rentals in Chepstow

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Top-rated cottage rentals in Chepstow

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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 in Chepstow
4.87 out of 5 average rating, 474 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, 124 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.

Superhost
The exterior of a stone cottage is shown, featuring a wooden door and large windows. A picnic table is situated nearby, along with a fire bowl filled with logs. A bicycle is propped against the wall, and the surrounding area includes gravel pathways and green vegetation.
Cottage in New Mills
4.88 out of 5 average rating, 229 reviews

Highlands Cottage | cider orchard | Wye Valley

Highlands Cottage is a detached, stone built converted stable with lots of rural charm and set in a beautiful apple orchard. It is tastefully converted; sleeps 4 and has a well equipped kitchen and open plan dining/living area, plus a walk in shower room. The South-facing patio has beautiful views across the valley, perfect for enjoying a meal. Free parking and good wifi. Numerous walks from the door, to pubs, forests and the River Wye. Short drive to Monmouth and lots of visitor attractions.

Top guest favourite
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, 225 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 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, 185 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 in Brockweir
4.99 out of 5 average rating, 247 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.

Guest favourite
A living room is displayed with a stone fireplace as a focal point. A comfortable chair is positioned next to a window seat adorned with cushions. A television rests on a side table, surrounded by a few books. Decorative wall art adds subtle character.
Cottage in Minchinhampton
4.97 out of 5 average rating, 231 reviews

Grade II listed historic Cotswolds cottage

A Grade II listed 2-bedroom cottage, in a charming Cotswolds area, steeped in history and character, with original windows, traditional flagstone flooring, stone walls, oak beams and a fireplace. All rooms have lovely little window seats. Enjoy your own orchard at the end of the garden, perfect for a BBQ or picnic. The Cottage also includes free off-street parking. We love the local walks, views and the quintessential little Cotswolds high street only minutes walk from the cottage.

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, 330 reviews

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.

Top guest favourite
The cottage's exterior is framed by a lush garden, featuring colorful flower pots and a gravel path. A shaded area with a green chair offers a peaceful spot to relax, while the soft sunlight illuminates the charming white facade and surrounding greenery.
Cottage in Scowles
4.96 out of 5 average rating, 320 reviews

Country cottage with private woodland and orchard.

Our beautiful beamed attached cottage complete with log burner is set in over 3 acres of private ancient woodland, in the Forest of Dean near the River Wye. The garden path leads down to a secluded orchard which is a haven for birds, deer & wildlife. The cottage is located in a quiet country lane, with walks to our local pubThe Ostrich Inn and town. We are close to all ammenities, cycle trails, river activities and the best of what the Forest of Dean and Wye Valley has to offer.

Top guest favourite
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, 148 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.

Superhost
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, 330 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!

Top guest favourite
An open living area featuring high vaulted ceilings with original beams. A cozy white sofa sits adorned with decorative pillows, complemented by a stylish armchair and modern dining table. Natural light streams through large windows, creating a bright and inviting space.
Cottage in Frome Vale
4.94 out of 5 average rating, 190 reviews

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.

Popular amenities for Chepstow cottage rentals

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  2. United Kingdom
  3. Wales
  4. Monmouthshire
  5. Chepstow
  6. Cottage rentals