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House vacation rentals in Chepstow

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Top-rated house rentals in Chepstow

Guests agree: these houses are highly rated for location, cleanliness, and more.

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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, 154 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.

Top 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, 676 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
The traditional cottage is partially obscured by lush greenery, featuring a white exterior and prominent chimneys. A conservatory is visible, and trees frame the surroundings, creating a tranquil and inviting setting in the heart of nature.
Home in Trelleck
5 out of 5 average rating, 102 reviews

Cute little Wye Valley cottage

Surrounded by woodland with hilltop views across the Wye Valley to Offa’s dyke, this eco friendly traditional Monmouthshire cottage is the perfect place to unwind and enjoy nature at its very best. Spend time in the garden listening to bird song and the gentle babbling of the stream or step out the gate to explore Cleddon Falls and beautiful view points along the Wye Valley walk. The medieval village of Trellech and Tintern Abbey are also within easy reach off or on road by foot, bike or car.

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, 254 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, 147 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
An ancient stone church stands amidst greenery, featuring a slate roof and tall arched windows. Surrounding the building are gravestones, set on a well-maintained lawn, with trees providing a natural frame. The structure is enhanced by a peaceful atmosphere, inviting moments of reflection.
Home in Frome Vale
4.94 out of 5 average rating, 199 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 on the western fringe of 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.

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, 272 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 cozy living area features a dark sofa adorned with decorative pillows and a yellow throw. A soft area rug sits beneath the furniture. Sunlight filters through the window blinds, illuminating the space and reflecting off a large wall mirror. A smart TV is mounted on the wall.
Home in Portishead
4.77 out of 5 average rating, 177 reviews

Beautiful Studio 1mile to Marina /Lake Grounds

This fully furnished, renovated space - studio apartment is nestled in a cul-de-sac developed by the renowned Free Mantle. It offers a bright open plan living space, kitchenette with appliances. En-suite finished to the highest standards with amenities. Enjoy watching Netflix, YouTube and general stations on an impressive 65 inch smart TV. Super fast broadband. If you need any assistance during your stay your hosts are right next door and happy to help.

Top 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, 1,100 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
Home in Itton
4.92 out of 5 average rating, 102 reviews

Charming Retreat in the Heart of Wye Valley AONB

Cosy modern retreat in peaceful rural Chepstow, set by Chepstow Park Woods. Perfect for walkers and nature lovers. Enjoy easy access to historic Chepstow Castle, stunning Tintern Abbey, and the charming market town of Monmouth. Bright open-plan space with garden views, comfy amenities, and flexible workspace. Close to Wye Valley, Bristol, and Cardiff for exploring or relaxing.

Top guest favorite
A spacious bed is dressed in crisp white linens, with accent cushions in grey and orange. A decorative plant sits in a vase nearby, complementing the dark blue wall behind. A softly glowing pendant light hangs above, enhancing the calm atmosphere of the room.
Home in Bath and North East Somerset
4.98 out of 5 average rating, 302 reviews

The Loft House - Beautiful House in Best Location

The Loft House is a charming, newly renovated house in the heart of Bath . A host of lovely cafes, restaurants and independent shops are right on the doorstep. The historic Circus is a stone's throw away with the Royal Crescent a short walk beyond. Heading south, you'll quickly reach Milsom Street which will take you down towards the Roman Baths, Abbey and Pulteney Bridge.

Top guest favorite
An inviting living space is illuminated by pendant lighting, showcasing a comfortable sofa and a classic Chesterfield armchair. A log burner is central to the room, surrounded by bookshelves. A dining table is set for four, complemented by decorative plants and wall mirrors.
Home in Gloucestershire
4.92 out of 5 average rating, 304 reviews

Stylish barn in The Forest of Dean

Nestled in the peaceful Gloucestershire countryside, this luxurious barn is the ideal getaway to escape the hustle and bustle of daily life. Relax in your own private hot tub overlooking the woodland or cosy up inside next to the log burner. Perfectly situated to explore everything the Wye Valley and Forest of Dean have to offer.

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 570 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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