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House holiday 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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Guest favourite
The barn features an expansive glass facade, allowing for ample natural light and unobstructed views of the surrounding landscape. A wooden deck extends outward, bordered by gravel. Inside, a spacious room can be seen with a super king-size bed and dining area.
Home
4.92 out of 5 average rating, 296 reviews

Unique Private Slad Valley Contemporary Chic Barn

Peglars Barn was completed in 2019, the entire front of this barn is glass which brings the stunning Slad Valley to you at all times, with nothing except the odd animal to distract you from your back to nature experience. This property has everything, blinds, super kingsize bed, en-suite walkin shower, laundry & loo, fully equiped kitchen, huge Smart TV, DVD, WiFi, Bose speaker, Nespresso machine, Laurie Lee trail walking map & other trails. Please read on for more local interest for your stay.

Guest favourite
Home
4.95 out of 5 average rating, 187 reviews

Tregaron Cottage, Upper Cwmbran

Nestled in the tranquil foothills of Blaen Bran Community Woodlands. A perfect, cosy getaway for couples, families & pets (plz NB there is an additional charge for pets) The cottage boasts exceptional mountain views. Perfectly situated for walkers & cyclists to explore the nearby trails inc BikePark Wales trail. 30 sec walk to The Bush Inn Pub, 3 min walk to The Queen Inn (recently reported as the worlds 1st vegan steakhouse), both friendly & welcoming, serving excellent meals & craft beers.

Superhost
A striking red sports car is parked on the gravel driveway in front of a historic stone-built townhouse. The three-story building is characterized by large windows and classic architectural features, set against a clear blue sky.
Home
4.81 out of 5 average rating, 124 reviews

Stunning 17th century Cotswolds townhouse annexe

Rounceval House is a marvellous 17th century stone-built town house in the shadow of the south Cotswolds escarpment on the famous Cotswold Way walk. It was an upmarket 11-bedroom boutique hotel until recently. New owners Richard and Leanne now run it as a family home and rent out the self-contained three-double bedroomed eastern annexe wing to guests. It's a lovely space. The bedrooms are exceptionally large. The double beds in them are also very large (either king-sized or super king-sized).

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
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
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
4.92 out of 5 average rating, 148 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
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
4.92 out of 5 average rating, 288 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.

Guest favourite
The historic Grist Mill is depicted, showcasing its stone façade and traditional cupola atop the roof. Lush greenery surrounds the building, with a pathway leading to the entrance. A garden area features outdoor seating, inviting leisurely moments outdoors.
Home
4.83 out of 5 average rating, 187 reviews

Grist Mill - listed Cotswold mill at Owlpen (1728)

The Grist Mill is an early 18th-century watermill which sleeps up to 8 in four double bedrooms. This listed Grade 2 landmark building has been restored as a gem of a holiday home, with contemporary comfort and style, surmounted by lantern and cupola. Enjoy open plan living in traditional style on the ground floor, and as you head up through the house you'll find cosy bedrooms and old machinery still in place, a relic of times past. Wooden beams, comfortable beds and new bathrooms.

Top guest favourite
The living room features a comfortable leather sofa set arranged around a central rug, with a log burner and wooden mantel as focal points. Large windows provide natural light, while framed photographs decorate the walls. A television is positioned for viewing convenience.
Home
4.97 out of 5 average rating, 227 reviews

Quiet Edwardian era House, Painswick

Welcome to our family owned Edwardian era house situated in Painswick. Renovated with hosting in mind, we'll have everything you need for a relaxing stay. Situated just off the Cotswold Way national trail, it's the perfect pit-stop for keen walkers (or runners!). If sight seeing is more your thing, the popular 18th Century Rococo Garden is just a 5 minute walk away. Ideally located for travel to Stroud, Cheltenham, Cirencester and Gloucester all within a 20 min drive.

Top guest favourite
The charming Cotswold stone cottage is framed by lush greenery and colorful flowers. A gravel pathway leads to the entrance, flanked by a small pond. The property features a symmetrical facade, with multiple gabled roofs and large windows reflecting natural light.
Home
4.93 out of 5 average rating, 323 reviews

Beautiful Cotswold Stone Cottage

Situated close to the Cotswold Way and the Gloucestershire Way footpaths, Close Cottage (the earliest building in Coberley circa 1550) really is in the heart of the Cotswold Hills. The self contained property comprises: two double bedrooms, fully equipped kitchen, shower room and a cosy lounge with wood burner. The traditional Cotswold stone cottage overlooks picturesque countryside and is situated within ten minutes drive from the beautiful and popular spa town of Cheltenham.

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
4.91 out of 5 average rating, 183 reviews

Self catering cottage, sleeps 4, in Portishead.

The early 18C cottage is a part of our home but totally 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. Both have tea and coffee making facilities. The property enjoys two bathrooms; each close to the each of the bedrooms. There is a large lounge with a wood burning stove, ample seating, TV/DVD player and a piano. The large kitchen has a range, microwave cooker and dishwasher.

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
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
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
4.95 out of 5 average rating, 1,102 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.

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 £15 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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