House vacation rentals in Chepstow

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Quick stats about house rentals in Chepstow

  • Total vacation rentals

    Explore 20 vacation rentals in Chepstow

  • Nightly prices starting at

    Chepstow vacation rentals start at G$2,088 GYD per night before taxes and fees

  • Verified guest reviews

    Over 670 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Wi-Fi availability

    20 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!

Top-rated house rentals in Chepstow

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

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Guest favorite
A charming historical house with a blend of stone and timber-framed architecture is set under a clear blue sky. The entrance features a black door framed by neatly trimmed greenery and colorful flowerbeds, showcasing the character of the village.
Home in Castle Combe
4.92 out of 5 average rating, 131 reviews

Luxury Cotswolds Cottage, Castle Combe (optional Hot Tub)

Luxury self-catering home in the heart of Castle Combe, perfect for family breaks or romantic weekends spent curled up in front of the fire. The spacious bedrooms (inc. super king four poster bed) all with sumptuous bed linen guarantee relaxation. The property was built in 1490 and is one of the oldest houses in the village, retaining its wealth of character including Henry VIII's original coat of arms painted above the fireplace. Rumour has it Henry VIII visited the village and this was painted in his honour. Although built in the 15th Century, this property has been renovated beautifully and you will stay in the lap of luxury! With the very best mattresses and bed linen, you will be treated to a 5-star self-catering experience. There is also a 4–6-person hydro-pool hot tub on the patio behind the house, unfortunately due to the energy crisis and the costs of heating and cleaning it, we offer this as an optional feature and charge an additional fee of £180 per stay if you want to use it. We have excellent heating throughout the house and the wood burning stove in the sitting room throws out a huge amount of heat. This is the most beautiful village in England (officially voted to be!) and the set of numerous block buster films and period dramas. We are a two minute walk to the Manor House complete with Michelin star restaurant 'the Bybrook', a world class golf course, Castle Combe Circuit racing and endless stunning walks along the river. There are two pubs, the White Heart does incredible sandwiches and hot food. Sal and Dave are a castle combe institution, and this is the pub we spend most time at. The Castle Inn is now owned by the Manor Hotel. The food is high end and the prices have followed it. Recommend to book and a good place for dinner. Please note, free parking is available outside the Castle Inn Hotel or White Hart pub and additional free parking available up the hill from the main square, roughly 2 minutes walking. However at peak busy periods you may find parking is further up the hill than you like, sorry, on a hot Saturday many people come to enjoy the walks around the village and it can get busy. You can use the space outside the Old Court House for loading and unloading, however we would recommend that you don't leave the car parked for long periods as there is a traffic warden who exercises the free distribution of parking tickets without prejudice! Please just check that you are not parked on a yellow line. This is a place you can do everything or nothing. Perfect to unwind in front of our wood burning stove set in a majestic fireplace. You will never want to leave! As the house is situated in the heart of Castle Combe please respect our neighbours and remember to keep any noise down to a minimum after dark.

Top guest favorite
The exterior of the barn conversion is shown, featuring a mixture of stone and wood materials. Bright flowers and greenery surround the entrance, along with patio seating. Large windows allow natural light to illuminate the interior, and a red front door offers an inviting focal point.
Home in Falfield
4.99 out of 5 average rating, 208 reviews

The Barn. Perfect for family & friends to meet up.

This very spacious barn conversion is the perfect place to meet family & friends, to relax and “re-connect”. The large fully equipped open plan kitchen and dining room join into the light and comfortable lounge to form the perfect social space plus there's a games room with full size table tennis! Extensive outside patios & gardens provide stunning views over the Severn Vale and wonderful sunsets. Three of the four bedrooms are on the ground floor; all have private en-suites with shower or bath.

Top guest favorite
An electric hot tub is positioned in a spacious garden, surrounded by lush greenery. Two steamer chairs are visible nearby, offering a relaxing area for guests. The hot tub features jets and bubbles, with clear blue water inviting for a soothing experience.
Home in Llanrothal
5.0 out of 5 average rating, 105 reviews

The Cart Shed-hot tub, up to 4 bedrooms

A peaceful & luxurious new stone conversion in the heart of The Monnow Valley. On the English/Welsh border. Electric Hot Tub, large mature enclosed garden, private driveway and parking. Sleeps up to 6. Up to 4 bedrooms. 1 dog welcomed. Rolling hills & beautiful countryside. From the location the views are magnificent. Doorstep footpath takes you 200 mtrs down to river Monnow where it can be followed to picturesque Llanrothal church & Tregate bridge within 1/2 mile.The location is truly idylic

Top guest favorite
The exterior of Colliers Cottage is showcased under a clear blue sky. The stone façade features red accents, with large windows that invite natural light. A wooden patio area is furnished with a dining table and chairs, offering a view of the well-maintained garden.
Home in Parkend
4.99 out of 5 average rating, 137 reviews

Colliers Cottage at The Barracks, Forest of Dean

Situated in the heart of the Forest of Dean, you will find Colliers Cottage. An ex-colliers cottage that has been extensively renovated in 2024, it comprises 2 bedrooms (1 with en-suite), family bathroom, kitchen, lounge (with sofa bed), dining room and a large, fully fenced private garden with off road parking If you want a stay where you are surrounded by nature, look no further! This is an ideal location for keen walkers, runners and cyclists with off road trails just a short distance away

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 Trellech
5.0 out of 5 average rating, 124 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
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, 172 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

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, 309 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
Home in Castle Combe
4.95 out of 5 average rating, 464 reviews

The Old Museum, Castle Combe

The Old Museum is a detached self-contained holiday home in the historic and picturesque village of Castle Combe. It is just short walk (200m) to the village centre with its pubs, cafe and restaurant. The Manor House Golf Club and Castle Combe Circuit are both within in walking distance and the footpath opposite connects up with a series of walks across the land of the Castle Combe Estate and beyond. The property enjoys private off-street parking, which is a rare find for the village.

Top guest favorite
Home in South Gloucestershire
4.95 out of 5 average rating, 220 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.

Guest favorite
Home in Cotham
4.95 out of 5 average rating, 102 reviews

Redland Suites: The Mews. Great Location & Sleep 4

This beautiful 2-bedroom high spec mews house sleeps 4 guests comfortably. A gorgeous open plan fully equipped kitchen and living area, two bedrooms with king sized beds, both have luxury en-suite bathrooms one with a waterfall shower and the other with a bath. The property also has a downstairs toilet and utility room. These are just some of the features to make your stay perfect. The high-end finish and furniture has been selected with your comfort in mind.

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, 1148 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.

Guest favorite
The country cottage features a classic stone exterior with a slate roof, surrounded by a lush green lawn and garden. A white parasol provides shade over the outdoor seating area, enhancing the inviting appearance of the property amidst the natural surroundings.
Home in Lower Wraxall
4.93 out of 5 average rating, 146 reviews

Delightful Cottage Retreat

Nestled in the heart of the idyllic village of Lower South Wraxhall, this beautiful country cottage is the perfect place to get away from it all. Just north of the historic town of Bradford on Avon, 20 minutes to Bath and sitting within the Cotswolds, the cottage is well placed for exploring. Beautifully decorated and well equipped for blissful summer days or cosy winter evenings you are guaranteed to have a special stay.

Popular amenities for Chepstow house rentals