House holiday rentals in Chepstow

Find and book unique houses on Airbnb

Quick stats about house rentals in Chepstow

  • Total holiday rentals

    Explore 10 holiday rentals in Chepstow

  • Nightly prices starting at

    Chepstow holiday rentals start at $14 AUD per night before taxes and fees

  • Verified guest reviews

    Over 600 verified reviews to help you choose

  • Wi-Fi availability

    10 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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Guest favourite
Home in Boddington
4.94 out of 5 average rating, 187 reviews

Boddington Mill

Boddington Mill is a stunning countryside retreat in the heart of the Cotswolds, steeped in history and rural charm. The building retains industrial mill parts which intersect multiple levels for a unique and generous living space. Its south-facing garden includes outside dining, wood-fired hot tub, and large lawn, home to wildlife and fruit-bearing trees. Inside, the three king sized bedrooms feature luxury bedding beneath vaulted, oak-beamed ceilings and period windows. Sky TV, Sonos speakers.

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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, 199 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.

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Guest favourite
Home in Painswick
4.94 out of 5 average rating, 166 reviews

Breathtaking Cotswolds Restored Chapel Valley View

Step into a rare and remarkable stay at ‘The Old Church’, a lovingly restored & renovated 1820s chapel nestled on the hillside in the idyllic Cotswolds village of Sheepscombe. This enchanting property blends timeless character & period charm with a relaxing contemporary feel. A truly unique picturesque countryside escape. Located in a tranquil woodland setting on the edge of Blackstable Nature Reserve with scenic valley walks, a rustic village setting, a playground & lovely pub down the lane.

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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, 113 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.

LocationFamilyLong stay

Top Guest favourite
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, 279 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.

ValueFamilyWalkability

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, 159 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

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Guest favourite
The exterior of a charming self-catering cottage features a whitewashed façade, wooden accents, and a welcoming front porch. A small stone path leads to the entrance, surrounded by a well-maintained garden with various shrubs and a seating area. Natural scenery frames the cottage in the background.
Home in Coed-y-paen
4.96 out of 5 average rating, 309 reviews

Forest Cottage

There are no hidden extra payments, the nightly fee is total. Self catering cottage, originally built in the 1800's, restored and extended to provide a high standard of accommodation. Set in private gardens which extend to 23 acres and with outstanding views across the Usk valley. The garden area provides 2 large decked viewpoints, Private parking. The property has retained its original stone spiral staircase which might prove difficult for guests with mobility issues or the very young.

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Top Guest favourite
A half-timbered manor house is set within a spacious, green landscape. The building is surrounded by lush trees, with a clear blue sky overhead. A peaceful freshwater lake and gently rolling hills are visible in the background, enhancing the tranquil atmosphere.
Home in Ross-on-Wye
4.92 out of 5 average rating, 298 reviews

The Game Larders

Wythall is a half-timbered manor house in a secluded and idyllic setting with garden, fresh water lake, wooded grounds and vineyards. You will enjoy peace and quiet here and see an abundance of wildlife. Wine tastings and vineyard tours are also available via appointment. The Game Larders is completely self contained and situated in the west wing of the manor house. It is well equipped and furnished, with access to ample parking space and central heating throughout. Pets are welcome.

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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, 299 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.

ValueFamilyBackyard

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, 161 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.

LocationFamilyGetting around

Top Guest favourite
The charming exterior of the period cottage features a stone façade with a blue door at the center. Two windows, framed with white shutters, are symmetrically placed on the upper level, while a warm light illuminates the entrance, enhancing the welcoming appearance.
Home in Chew Magna
4.93 out of 5 average rating, 104 reviews

Charming end of terrace 2 bed country cottage

Welcome to this delightful period cottage in the picturesque village of Chew Maga. This two-bedroom home combines timeless charm with modern comforts. Situated in the heart of Chew Magna, the cottage is just a short 5 minute stroll from the village’s extensive amenities. The cottage is surrounded by scenic walking trails and a short walk to Chew Valley lake and close to the Mendip Hills. Bristol airport is 10 minutes away, Bath 10 miles away and Bristol 6 miles away.

LocationFamilyCheck-in

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
4.92 out of 5 average rating, 133 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

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Popular amenities for Chepstow house rentals

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