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House holiday rentals in Chepstow

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Top-rated house rentals in Chepstow

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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, 189 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, 103 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
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, 260 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 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, 127 reviews

Elegant Family-Friendly Retreat Stunning Views

Beautiful Family & Friends Retreat in the Wye Valley & Forest of Dean Looking for 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 of on-site activities for all ages. River kayaking, wild swimming, fishing, horse riding, golf, zip wire & inland surfing. You'll love meeting our friendly chickens( & enjoy fresh eggs during your stay!

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, 289 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.

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, 151 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
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, 277 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.

Top guest favourite
A dining table is set with a neutral table runner and natural placemats. Elegant glassware and neatly arranged plates accompany a vase filled with greenery and white flowers, creating a refined dining experience against a textured stone wall.
Home in Bath and North East Somerset
4.98 out of 5 average rating, 109 reviews

Stunning, stone property with city views

Immaculately presented two bedroom property located moments from the bustling city streets. This stunning property has the most beautiful views from the terrace, overlooking the UNESCO city of Bath, large living and dining spaces, two bedrooms both with ensuite bathrooms and off street parking. A real gem in the tranquility of elegant Widcombe with an abundance of local cafes, shops, pubs and restaurants only a short stroll away. Come, refresh and relax!

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, 1,105 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 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, 190 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.

Top 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
4.97 out of 5 average rating, 297 reviews

Forest Cottage

Self catering cottage, originally built in the 1800's, restored and extended to provide a high standard of accommodation. Set in private gardens with outstanding views across the Usk valley. The garden area provides 2 large decked viewpoints, Private parking. The property has retained it's original stone spiral staircase which might prove difficult for guests with mobility issues or the very young.

Top guest favourite
Home in Devauden
4.92 out of 5 average rating, 104 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.

Popular amenities for house rentals in Chepstow

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 $26 SGD per night before taxes and fees

  • Verified guest reviews

    Over 570 verified reviews to help you choose

  • Wifi availability

    10 of Chepstow holiday rentals include wifi 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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