Vacation rentals in Chepstow

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Top-rated vacation rentals in Chepstow

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Guest favorite

A tranquil garden scene features a lush array of greenery and colorful blooms. A small pond surrounded by vibrant plants reflects the blue sky. Towering trees and flowering vines enhance the serene atmosphere, inviting exploration and appreciation of nature.

Cottage in Tidenham Chase

4.9 out of 5 average rating, 128 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

Guest favorite

An open-plan area is featured, with a wooden dining table at the forefront. Natural light enters through multiple windows, illuminating the cozy living space with a blue sofa and decorative shelves along the wall. Warm lighting from hanging fixtures adds to the inviting atmosphere.

Cottage in Chepstow

4.86 out of 5 average rating, 445 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.

Top guest favorite

An electric vehicle charging station is mounted on a weathered stone wall. The unit is encased in white plastic, featuring a green accent. Clear instructions are displayed on the front, ensuring ease of use for electric vehicle owners.

Chalet in Boughspring

4.89 out of 5 average rating, 137 reviews

The Studio

A refurbished stone built, 1 bedroom detached chalet in an extremely quiet rural location close to good traffic links, long-distance footpath, Forest of Dean, Wye Valley and the National Dive Centre. Large lounge with log burner, sofa and dining table. Open plan kitchen with electric oven, induction hob, microwave, fridge and toaster. One bedroom with king size bed, ensuite shower and wc. Private patio and access to garden. 5 min drive to shops in Chepstow, 40mins to Bristol / Cardiff.

Top guest favorite

Townhouse in Chepstow

4.94 out of 5 average rating, 234 reviews

Chepstow Town. Welsh Cottage.

The house is in the centre of the beautiful old market town of Chepstow. Nestled on the Welsh / English border. We are just a stone's throw from the ancient castle and the impressive Priory Church of St Mary. Within walking distance of the Chepstow Racecourse and a stroll from the railway and bus stations. 300yds from the River Wye and central to all restaurants and cafes etc. Situated near the AONB Wye Valley and Forest of Dean. Please note the property has a Jack & Jill bathroom upstairs.

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, 164 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

Guest favorite

The view from an ancient window showcases a stone building surrounded by a well-kept garden. A central pathway leads through lush green grass and flowers, inviting exploration. The building features multiple windows and stone detailing, highlighting its historic charm.

Castle in Chepstow

4.93 out of 5 average rating, 179 reviews

Welsh Gatehouse: Luxury 13th Century Medieval Home

The Welsh Gatehouse is a beautiful historic house with modern amenities. Imagine staying in a fairy tale castle built in 1270. The thick walls, ancient windows & steep spiral staircase say 'history'. Romantic log fires keep you warm you in winter, & the thick walls keep you cool in summer. Views from the top of the tower are extraordinary over the Severn Bridges and the Breacon Beacons (NB we call this the terrace in our description below). Unique, luxurious, quirky yet comfortable.

Top guest favorite

Cottage in Saint Briavels

5 out of 5 average rating, 311 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 favorite

The exterior of the bungalow is framed by lush greenery and colorful wildflowers. A compact private patio features a blue table and chairs, ideal for outdoor dining. The entrance is accentuated by a small overhang, adding charm to the environment.

Bungalow in Caldicot

4.98 out of 5 average rating, 210 reviews

Yeomans Lodge - Chepstow, Newly renovated.

Located within the grounds of the owners house, Yeomans Lodge is a newly renovated, quirky, self-contained, compact bungalow. It is a perfect location if you’re looking to escape to the countryside. The historic town of Chepstow and magnificent Wye Valley is a short drive away. Please note that the airbnb is in Crick, Chepstow, on some occasions the airbnb g00gle link takes you to Yeomans Acre in Gloucester which is the wrong location. Trying to sort the issue with Airbnb.

Top guest favorite

An outdoor seating area features a dark wicker sofa with light cushions, accompanied by a matching coffee table and side table. A large umbrella provides shade, while vibrant flowers in pots add color to the stone-paved patio surrounded by a lush green landscape.

Apartment in Gloucestershire

4.99 out of 5 average rating, 122 reviews

Idyllic Country Retreat in the Forest of Dean

Set in the grounds of a magnificent country home with far reaching stunning views over the River Severn and beyond. This is a perfect place to escape and unwind from the daily hustle and bustle of life. Near to Chepstow and with easy access to the M4 & M5 Motorways and only 2 hours drive from London, 30 minutes from Bristol and 40 minutes from Cheltenham. This cosy studio apartment has only recently been completed to an exceptionally high standard.

Top guest favorite

The exterior of a spacious stone house is displayed amidst lush greenery on a sunny day. Neatly trimmed hedges and ornamental topiary enhance the garden. The architecture features a mix of stone textures and inviting windows, providing charm and character to the property.

Apartment in Saint Arvans

4.93 out of 5 average rating, 114 reviews

The Nursery Wing - Wyndcliffe Court

The Accommodation is just off the Wye Valley walk at Upper Wyndcliff, a spacious and comfortable self-contained first floor flat within a private family house and garden with fabulous views. Guests can explore the beautiful gardens - which they may have seen featured in the May 2022 edition of "The English Garden". There are also wonderful walks and cycle rides from the door to Tintern, Chepstow and the AONB of the Wye Valley.

Guest favorite

A scenic riverside path is depicted, lined with golden grasses and bordered by the water. Distinctive cliffs rise in the background, while a small boat can be seen on the calm river. A few benches are positioned along the path, creating a peaceful outdoor space.

Cottage in Monmouthshire

4.88 out of 5 average rating, 430 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.

Top guest favorite

A white dog lies peacefully on a gravel surface, surrounded by vibrant flower pots. The pots are filled with colorful petunias, adding a cheerful touch to the outdoor setting.

Condo in Earlswood

5 out of 5 average rating, 250 reviews

Luxurious homely and cosy 1st floor apartment.

The Folly is on the first floor and is part of a contemporary country house set in four acres of gardens and paddocks. It is fully furnished to a high standard and very private. Open plan with dual aspect, lovely views to front and rear with balcony and seating overlooking the garden. King size and single bedrooms with immaculate shower room. Perfect rural location to escape to the country to re-charge and relax.

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Popular amenities for Chepstow vacation rentals

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Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Chepstow

Top guest favorite

Cottage in Brockweir

5 out of 5 average rating, 76 reviews

Birch Cottage with woodland sauna

OliverRating, 5 stars3 weeks ago

We had a really lovely time at Birch cottage. Despite only staying for a couple of days we felt right at home and fell in love with the area. The house is well equipped and beautifully decorated, and the Sauna was a fantastic experience. Phil was very helpful and went out of his way to make us feel welcome, I'm sure we'll be back in the not too distant future!

Top guest favorite

A vibrant carpet of bluebells covers the forest floor, surrounded by lush green foliage and soft, light filtering through the trees. The scene captures a serene natural setting, inviting calm and tranquility.

Cottage in Saint Briavels

4.88 out of 5 average rating, 52 reviews

Green Gables Country cottage annexe

MelindaRating, 5 stars2 days ago

We had a lovely stay. The annexe is cosy, clean and had everything we needed for our 1 night stay. Anne was kind enough to leave jigsaws and Lego for our 3 year old to play with, which was really appreciated, and even made my partner a birthday cake! The location is also great for visiting Puzzlewood and the surrounding areas (less than 10 minute drive). We would happily stay again.

Top guest favorite

A balcony setting is shown, featuring a charming glass pitcher and a succulent plant atop a wooden table. The view includes a verdant hillside and quaint rooftops nestled in the landscape, framed by a wrought-iron railing that adds a rustic touch.

Cottage in Brockweir

4.97 out of 5 average rating, 74 reviews

Stone Cottage with a splendid Wye Valley View

JennyRating, 5 stars1 week ago

We had a lovely stay at Riverview. it is situated in a lovely, scenic valley. Walking distance to Tintern Abbey and other lovely walks nearby. The cottage is comfortable and equipped with everything you need. we will definitely return should the opportunity arise.

Guest favorite

A lively horse racing scene captures multiple horses and jockeys at full stride on a green racecourse. Spectators fill the grandstand in the background, creating a sense of excitement. The horses wear numbered saddle cloths, and the varied colors of the jockeys' silks add visual interest to the image.

Vacation home in Monmouthshire

4.95 out of 5 average rating, 85 reviews

Spacious Chepstow home with private garden & patio

KevinRating, 5 stars3 weeks ago

We really enjoyed our short stay at Anna's house. It was clean, tidy, looked to have been recently decorated and had everything we needed to enjoy our time in Chepstow. It was very well placed for the town centre being no more than 10 minutes walk down the hill. There was also a nice Pub a few minutes up the hill called 'Two Rivers' where we went for a drink one night and also enjoyed a good Breakfast their on our way home.

Top guest favorite

A scenic view of the Cotswold Way is presented, featuring historic stone structures against a soft sunset sky. Pathway signs are visible, guiding walkers along the lush green landscape with dry stone walls and mature trees, inviting exploration of the surrounding natural beauty.

Condo in Thornbury

4.99 out of 5 average rating, 382 reviews

Delightful, comfortable, warm home away from home

ChrisRating, 5 stars1 week ago

Great place to stay for a few days, easy to get to all the places I needed to visit and easy to find. Very friendly host.

Guest favorite

The light-filled living area features a cozy seating arrangement with a couch and a rocking chair. A dining table with four chairs is positioned near large open doors, offering expansive views over the countryside. A Scandinavian wood burner adds warmth to the space.

Loft in Stroat

4.91 out of 5 average rating, 115 reviews

The Loft - Window on the Severn

CharlotteRating, 5 stars6 days ago

What a lovely spot. Juliet was a fab host, and the flat was cosy and with beautiful views. Wouldn’t hesitate to come and stay again.

Top guest favorite

The entrance features a welcoming porch with decorative hanging planters. A bench is positioned beside the entrance, with brick planters lining the pathway. The exterior walls are painted in a soft red hue, complementing the black door and trim.

Guest suite in Tockington

4.96 out of 5 average rating, 396 reviews

The Dairy - Quaint village stay

TomRating, 5 stars2 weeks ago

Lovely village, you can see Wales from the top of the hill as you drive in. Really nice, supper clean little self-contained flat. Smart TV was great too. Paddle stairs that you use to access the sleeping mezzanine area, are a little tricky if you had any kind of disability. Not complaining, as this is fully disclosed in the advert, but worth highlighting.

Top guest favorite