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
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, 198 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.

Guest favorite
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.

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, 112 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, 278 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, 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

Guest favorite
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, 308 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.

Top guest favorite
Home in South Gloucestershire
4.95 out of 5 average rating, 211 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 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, 160 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
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, 1,129 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
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

Guest favorite
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
4.92 out of 5 average rating, 153 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.

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, 230 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 ﺩ.ﺇ 37 per night before taxes and fees

  • Verified guest reviews

    Over 600 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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