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House vacation rentals in Chepstow

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Top-rated house rentals in Chepstow

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Top guest favorite
A private courtyard patio is visible, featuring wooden fencing and vibrant greenery. A small round table is surrounded by two rustic chairs. The backdrop offers an expanse of grassy fields and trees, illuminated by natural light under a partly cloudy sky.
Home in COLEFORD
4.96 out of 5 average rating, 138 reviews

Individual, detached Annexe…

This individual Annexe is situated near the wonderful market town of Coleford in the heart of the Forest of Dean, which has all the amenities needed to make your stay enjoyable and is an ideal base to explore the area. There are many places to visit, such as, Puzzlewood, (walking distance), Clearwell caves, Symonds Yat and the Wye Valley. There is a footpath that leads directly from the property into the forest so you can enjoy walking and biking. There’s also two 18 hole golf courses nearby.

Guest favorite
A spacious lodge interior features a comfortable double bed with a premium mattress, set against a backdrop of artistic wall decor. Large glass doors provide natural light and lead to a garden area, while a wall-mounted smart TV and a kitchenette are visible in the background.
Home in Patchway
4.94 out of 5 average rating, 636 reviews

BEAUTIFUL Tiny House: Whitsun Lodge

Tiny little lodge/House in Bristol. Detached from our house with access to the garden. 10 minutes drive from THE WAVE. 30 seconds walk from Aerospace Bristol (Concorde museum) Great links to the City Centre Comprising of full kitchen, En-suite bathroom and shower, comfy double bed (premium mattress) Smart TV already connected to Netflix/NowTV/Disney+ Use of the washing machine if you need Me, My wife Charlee, My baby son Finley and our little Dog Louie look forward to welcoming you 😄

Top guest favorite
A bright and inviting room is filled with natural light from large windows dressed with soft curtains. The cozy area features a spacious bed with light bedding, a textured sofa, and a circular coffee table. Artwork hangs above the bed, adding a touch of color.
Home in Thornbury
4.98 out of 5 average rating, 218 reviews

Birch Cottage

Set in the Countryside just outside the market town of Thornbury, Birch cottage is moments away from Bristol, Wales and 30 mins to the Cotswolds. Standing in its own private garden with stunning views across the river Severn into Wales, friendly sheep are your neighbours. The Cottage is brand new, fitted to a high standard with its own kitchen, en suite and private gated parking 10 mins from the M4/5. Close by are:The Wave, Clifton Bridge, Wye Valley, Bristol docks and Thornbury Castle.

Top guest favorite
The exterior of a charming stone cottage is presented, featuring a warm facade adorned with ivy. A welcoming entrance opens into the space, while a small courtyard area is visible, surrounded by greenery and gravel pathways, enhancing the tranquil atmosphere.
Home in Tidenham Chase
4.92 out of 5 average rating, 142 reviews

The Dairy

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 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/cosy-wye-valley-getaway

Guest favorite
A charming detached lodge is surrounded by a well-maintained garden, featuring a mix of stone and wooden design elements. The inviting entrance is framed by potted plants, with a patio area of stepping stones leading to lush green grass. The exterior is bathed in natural light under a partly cloudy sky.
Home in Raglan
4.88 out of 5 average rating, 185 reviews

Willsbrook Lodge

This little piece of heaven sits in the centre of the village of Raglan, within the grounds of Willsbrook House, just moments from its castle & within walking distance of a pub, restaurant, village Supermarket (Tesco 7am-11pm) & award winning butcher. Ideally located for exploring Tintern Abbey, floral Usk, Abergavenny and Monmouth (all under 10 miles) visitors can also enjoy golf courses abound and the Breacon Beacons, Offa's Dyke, Wye and Usk Valleys which all provide good walking.

Guest favorite
The side of a spacious barn conversion is shown, featuring large glass doors that provide expansive views of the surrounding fields. Lush greenery and blooming flowers line the foreground, creating a natural border against the rustic stone structure.
Home in Tidenham
4.92 out of 5 average rating, 122 reviews

Elegant Family-Friendly Retreat Stunning Views

Beautiful Family & Friends Retreat in the Wye Valley & Forest of Dean Looking for the perfect getaway for your family and friends. This stylish and spacious barn conversion offers everything you need for a memorable stay, with breathtaking views, incredible outdoor adventures, and plenty of on-site activities for all ages. River kayaking, wild swimming, fishing, horse riding, golf, zip wire & inland surfing. You'll love meeting our friendly chickens( & enjoy fresh eggs during your stay!

Top guest favorite
The cottage features a charming garden surrounded by greenery, with a well-maintained pathway leading to the entrance. Colorful flower pots are arranged along the stone path, and hints of the rustic stone exterior of the building are visible, creating a tranquil outdoor space.
Home in Portishead
4.91 out of 5 average rating, 174 reviews

Self catering cottage, sleeps 4, in Portishead.

The early 18C cottage is a part of our home but totally self contained. It retains many of the features of the time and is full of character. The two doubles are a good size and have wardrobes and shelving. Both have tea and coffee making facilities. The property enjoys two bathrooms; each close to the each of the bedrooms. There is a large lounge with a wood burning stove, ample seating, TV/DVD player and a piano. The large kitchen has a range, microwave cooker and dishwasher.

Top guest favorite
The main entrance features a solid light gray door with a decorative window and a traditional door knocker. A wall-mounted lantern provides illumination, while a small basket of flowers adds a welcoming touch at the base. The cottage number is displayed beside the door.
Home in Aylburton
4.96 out of 5 average rating, 142 reviews

Cosy cottage in village centre.

Newly renovated and restored to a very high standard, the cottage has retained its traditional features.It is warm and cosy located in the centre of the popular village of Aylburton. Enclosed rear terrace and secure bike storage. The fitted kitchen is fully equipped with everything you need to prepare meals, having said that, there's a great pub next door. There is also a BBQ and outdoor seating, just a step up from the kitchen to enjoy a morning coffee on the sunny patio.

Top guest favorite
The cottage is set on a hillside, surrounded by lush greenery and trees. A gentle slope leads to the well-maintained garden, with ferns and native plants framing the stone structure. The sky is bright blue with scattered clouds, enhancing the peaceful rural setting.
Home in Amberley
5 out of 5 average rating, 252 reviews

Magical cottage set within a woodland glade

Badgers Bothy is set within a woodland glade in the grounds of the 16th century Amberley Farmhouse and provides the most unique and charming country escape. Our idyllic cottage is set on the edge of Minchinhampton Common (located in an AONB) and with miles of footpaths which are perfect for those wishing to explore the Cotswolds. This beautiful cottage exudes an aura of peace and tranquillity and a haven for those wishing to escape the hustle and bustle of a busy life.

Guest favorite
A spacious stone cottage is surrounded by lush greenery, with a pathway leading to the entrance. The exterior features a mix of stone and wood elements, creating a rustic charm. Large windows allow natural light to brighten the interior spaces.
Home in Whitebrook
4.95 out of 5 average rating, 1,065 reviews

Adjoined Stone Cottage Wye Valley (Five Springs)

Self-catering cottage in a small quiet Wye Valley village in in the hills above Monmouth. Set in 6 acres of woodland and hidden gardens. Large bedroom with comfortable king (60") & single bed, lounge with log burner, TV & WiFi. Stunning large spa room with sauna, shower, jacuzzi & small toilet room. Kitchen with induction hob, grill and fan oven, microwave, washing machine, tumble dryer and fridge freezer, separate bathroom with toilet.

Top guest favorite
A modern living space is portrayed, featuring a large black sofa and a wooden dining table with chairs. Bright natural light enters through two windows, illuminating the room. A bedroom is visible in the background, with a bathroom on the right, highlighting a clean and contemporary design.
Home in Tregare
4.98 out of 5 average rating, 265 reviews

Waterloo Too - Guest house in a wildlife paradise

One mile from Raglan this little house is seriously comfortable. A great base for anyone visiting the Welsh borders. It has its own garden but there is plenty more garden, a pond and an orchard to explore and relax in. The wildlife and night skies here are spectacular! Well equipped with a huge sofa, WiFi, TV and Netflix. The bathroom has a bath as well as a shower. If there is anything you need just ask the owner who lives next door.

Top guest favorite
The exterior of Wycke Cottage features charming stone walls adorned with lush green vines. Multiple windows allow natural light to fill the space, while potted plants in various sizes enhance the entrance. A clear blue sky creates a serene backdrop.
Home in Painswick
4.98 out of 5 average rating, 147 reviews

Cottage luxe in The Cotwolds

Wycke Cottage welcomes you with unequivocal charm and a little luxe at every turn. Hunker down in style in the picture-perfect Cotswold setting in the heart of Painswick. This 400-year-old cosy cottage, sits opposite the historic church. With stunning sunset views across to the church's beautiful spire and clockface, and its much storied 99 cloud-like yew trees, this stay offers the quintessential Cotswold experience.

Popular amenities for Chepstow house rentals

Quick stats about house rentals in Chepstow

  • Total vacation rentals

    Explore 10 vacation rentals in Chepstow

  • Nightly prices starting at

    Chepstow vacation rentals start at G$4,183 GYD per night before taxes and fees

  • Verified guest reviews

    Over 540 verified reviews to help you choose

  • Wi-Fi availability

    10 of Chepstow vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chepstow rentals

  • 5 Average rating

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

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