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House holiday rentals in Chepstow

Find and book unique houses on Airbnb

Quick stats about house rentals in Chepstow

  • Total holiday rentals

    Explore 20 holiday rentals in Chepstow

  • Nightly prices starting at

    Chepstow holiday rentals start at $17 NZD per night before taxes and fees

  • Verified guest reviews

    Over 670 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Wi-Fi availability

    20 of Chepstow holiday 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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Top Guest favourite
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, 204 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 favourite
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, 116 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 favourite
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, 167 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 favourite
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
4.92 out of 5 average rating, 195 reviews

Self catering cottage, sleeps 4, in Portishead.

The early 18C cottage is a part of our home but totally separate and 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. The property enjoys two bathrooms; each close to each of the 2 bedrooms. There is a large lounge with a wood burning stove, ample seating, TV and a piano. The large kitchen has a range, microwave cooker and dishwasher. In the utility room there is a washing and tumble drier.

Top Guest favourite
A spacious outdoor patio features a dining table set for a meal, surrounded by chairs. A shaded umbrella stands nearby, and greenery accents the area. The backdrop includes the rustic barn and expansive countryside views under a partly cloudy sky.
Home in Backwell
5 out of 5 average rating, 189 reviews

Beautiful Barn near Bristol in Picturesque Setting

Holly Tree Barn is a new modern conversion surrounded by lovely countryside, on the doorstep of Bristol and near Bath . Ideal for the Balloon Fiesta, the Airport and University Graduations. Bristol is easily reachable by train, bus, cycle path or car. Glastonbury, the Cotswolds and the beach are an easy drive. The Barn is down a quiet lane with village shops, pubs and the train station a 10 min walk. It is near public footpaths allowing you to explore the valley, walk, cycle and unwind.

Top Guest favourite
Home in South Gloucestershire
4.95 out of 5 average rating, 218 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 favourite
A charming two-story farmhouse is depicted in the image, featuring a classic white exterior. The front garden is adorned with vibrant red flowers and well-maintained greenery. A set of stone steps leads up to the entrance, with seating available on a small patio area.
Home in Hengoed
5 out of 5 average rating, 306 reviews

Unique Cosy Retreat - Spacious 3-Bed Farm House

Escape to a cozy, 17th-century Grade II listed farmhouse steeped in history and charm. Tucked away down a quiet lane, Cascade House is set within 1.5 acres of mature gardens, offering a peaceful sanctuary for couples and families. Explore beautiful walking routes throughout the local area or take advantage of our secure storage for bicycles. With ample gated parking and plenty of space to breathe, this historic retreat is the perfect base for your next countryside adventure.

Top Guest favourite
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, 166 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 favourite
A cozy living area is highlighted by a stone fireplace, where a gentle flame burns. Plush red sofas with patterned cushions surround a stylish coffee table adorned with decorative items and candles. Large windows draped with soft fabric allow natural light to filter in.
Home in Bath and North East Somerset
4.98 out of 5 average rating, 160 reviews

Stunning Lansdown Crescent Mews House with parking

Lansdown Crescent is a well-known example of Georgian architecture and a short walk from the famous Royal Crescent. Sitting quietly behind this iconic address you'll find this beautifully converted, lavish Upper Lansdown Mews house. Just a ten minute saunter from Bath centre, this truly luxurious two-bedroom retreat is brimming with the finest fixtures and finishes, complimented by a private terrace, mood lighting, carefully chosen furniture and artwork aplenty.

Top Guest favourite
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, 1,137 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 favourite
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
4.93 out of 5 average rating, 135 reviews

Elegant Family-Friendly Retreat Stunning Views

Beautiful Family & Friends Retreat in the Wye Valley & Forest of Dean. 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 off site activities for all ages. River kayaking, wild swimming, fishing, horse riding, golf, zip wire & inland surfing. Nightly rate includes 15% Airbnb fee

Guest favourite
The charming grade II listed cottage features a traditional stone facade with a thatched roof, nestled among lush greenery. A wooden front door is framed by manicured hedges and flowering plants, creating an inviting entrance to the historic property.
Home in Lower South Wraxall
4.91 out of 5 average rating, 158 reviews

Idyllic Historic Cottage

This charming character grade II listed cottage, built in the 1600's is set the middle of the beautiful village of Lower South Wraxhall. Ideally positioned just five minutes from the historic town of Bradford on Avon, twenty minutes from the UNESCO city of Bath and sitting within the Cotswolds. Nestled in an exquisite cottage garden, the property is fully equipped for summer garden bbq's or cosy winter evenings by the fire.

Popular amenities for Chepstow house rentals

  1. Airbnb
  2. United Kingdom
  3. Wales
  4. Monmouthshire
  5. Chepstow
  6. House rentals