Holiday Rentals in Chepstow

67 available vacation rental offers

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Chepstow holiday rentals
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Best Holiday rentals and Airbnb offers in Chepstow

Best family friendly Chepstow holiday rentals

Among the 67 accommodations in Chepstow, here are the 4 best family friendly rentals

The Potting Shed At Mathern Palace - Chepstow
9.4 3 reviews

The Potting Shed At Mathern Palace

cottage, Mathern
The Potting Shed is a restored 19th-century barn located on the grounds of Mathern Palace, a Grade I listed building dating back to 1408, just a short walk from the village of Mathern and its pub, The Millers Arms. The surrounding area offers picturesque countryside walks and is within easy reach of Caerwent Roman Town and Thornbury Castle.
This charming cottage has two bedrooms and can accommodate up to four guests. It features a spacious open-plan kitchen/diner, a separate lounge, a gravel front garden and a shared back garden, plus a Smart TV with Netflix and Prime Video apps, and a welcome pack with local recommendations.
Wallhope Retreat - Chepstow, Spectacular Views - Chepstow
10 36 reviews

Wallhope Retreat - Chepstow, Spectacular Views

cottage, Chepstow
This Chepstow cottage, situated within 4.8 kilometres of the River Wye, Chepstow Castle, Chepstow Museum, and Symonds Yat Rock, offers a peaceful rural retreat near major attractions.
The 119 square metre property sleeps four guests in two bedrooms and two bathrooms, boasting a jacuzzi, private garden with barbecue, free Wi-Fi, and ample parking.
The Elements Residence - Chepstow
10 1 review

The Elements Residence

house, Chepstow
This 10-bedroom, 8-bathroom residence is located in Chepstow's town centre, providing easy access to local shops and attractions.
This property offers 275 square meters of living space, featuring a kitchen equipped with a fridge, freezer, microwave, and dishwasher, alongside a garden and parking.
Wallhope Escape - Sleeps 6 Guests  In 3 Bedrooms - Chepstow
No reviews

Wallhope Escape - Sleeps 6 Guests In 3 Bedrooms

cottage, Chepstow
Wallhope Escape, a rural retreat on a working farm, is situated in tranquil countryside near Chepstow, a short drive from the Wye Valley Area of Outstanding Natural Beauty and Chepstow town centre. This 144 square meter holiday home sleeps six guests across three bedrooms and three bathrooms, featuring a kitchen with a dishwasher, fridge, and microwave, plus a garden, parking, and two private hot tubs for a secluded getaway.

Best Chepstow holiday rentals with parking

Edge Barn - Chepstow
9.7 179 reviews

Edge Barn

house, Woolaston
Edge Barn is situated in Woolaston, a tranquil village just 29 kilometres from Bristol Parkway Station and 37 kilometres from Bristol Temple Meads Station. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The property features two bedrooms and one bathroom, spanning 110 square metres and accommodating up to six guests. Edge Barn boasts a fully equipped kitchen, a private garden with river views, free Wi-Fi, and private parking, providing everything you need for a comfortable stay.
Cromwell House, Central Chepstow - Chepstow
9.8 147 reviews

Cromwell House, Central Chepstow

apartment
This charming flat is situated in the heart of Chepstow, a historic town in Monmouthshire, just a short walk from Chepstow Castle. It's received excellent ratings for location, cleanliness and user experience.
The apartment has two double bedrooms, a spacious kitchen with dining space, and a bathroom with a bath and shower, comfortably accommodating up to four guests. It's fully equipped with everything you need for a comfortable stay, including Wi-Fi, and its recent refurbishment ensures a modern and clean environment.
Cosy Private Studio. Fast Wi-fi & Parking. - Chepstow
9.8 103 reviews

Cosy Private Studio. Fast Wi-fi & Parking.

apartment
Caldicwtch Tiny home is a quiet, self-contained property located in a cul-de-sac in Monmouthshire, just 5km from Broomes' Event Centre and a short walk from local amenities. The property has been consistently rated excellent by guests for its cleanliness, location, and overall experience.
The tiny home has one bedroom and one bathroom, comfortably accommodating up to 3 guests. It features a modern design with smart TVs, super-fast Wi-Fi, and a self-service laundry facility nearby.
Pet Friendly 'Home From Home In The Wye Valley Wales - Chepstow
10 6 reviews

Pet Friendly 'Home From Home In The Wye Valley Wales

cottage, Chepstow
Clares Cottage is a charming 2-bedroom property located just 3 kilometres from the historic town of Chepstow, nestled in the peaceful Lower Wye Valley, on the border of Wales and England. The cottage enjoys a secluded country setting, surrounded by stunning countryside views and a half-acre organic garden.
The cottage offers a spacious living area and garden, ideal for families or groups of up to 4 guests. It comes equipped with modern amenities including a fully fitted kitchen, an electric car charging point, and a cosy log burner, perfect for relaxing evenings.

Frequently asked questions about holiday rentals in Chepstow

  • What are some interesting places to visit in or near Chepstow?

    Chepstow Castle is a must-see, it's a stunning Norman castle with a rich history. The town itself is lovely, with independent shops and pubs. If you're looking for something a little further afield, Tintern Abbey is only a short drive away and is worth a visit.
  • What are the best Airbnb and vacation rentals in Chepstow?

    Broadrock Accommodation - Clock Cottage, Chepstow Town - Welsh Cottage and Sedbury Farm Cottages #2 are the most popular Airbnb and vacation rentals in Chepstow among travelers.

  • Which walking or cycling routes are the best in Chepstow?

    The Offa's Dyke Path runs right through Chepstow, offering stunning views of the Wye Valley. For a shorter walk, try the Chepstow Town Trail, which takes you past some of the town's historic landmarks. If you're a cyclist, the Wye Valley Cycle Path is a great option, with flat, scenic routes.
  • What are the most popular Airbnbs in Chepstow?

    Among the Airbnbs in Chepstow, Chepstow Town - Welsh Cottage, Sedbury Farm Cottages #2 and Peaceful - Rural Apartment With River Views are the most popular ones.

  • What sports or outdoor activites can visitors enjoy in and around Chepstow?

    Chepstow Racecourse hosts horse racing throughout the year. There are also plenty of opportunities for kayaking and canoeing on the River Wye. For something more adventurous, try rock climbing at the Chepstow Climbing Centre.
  • What are the best vacation rentals with a pool in Chepstow?

  • What other towns or cities can be easily accessed from Chepstow?

    You're ideally located for exploring the area. You can easily reach the city of Bristol in under an hour, and Cardiff is about an hour and a half away. The historic town of Monmouth is just a short drive up the Wye Valley.
  • What are the best rentals for families and kids in Chepstow?

    The best rentals for families and kids in Chepstow are Broadrock Accommodation - Clock Cottage, Chepstow Town - Welsh Cottage and Sedbury Farm Cottages #2.

  • What amenities are commonly available in vacation rentals in Chepstow?

    Most vacation rentals in Chepstow offer basic amenities like Wi-Fi, TV, and a washing machine. Many also have private gardens, off-street parking, and a fully equipped kitchen. You'll find some with more luxurious features like hot tubs and swimming pools, depending on your budget.
  • What are the best rentals or Airbnbs with a jacuzzi in Chepstow?

    The best vacation rentals or Airbnb with a jacuzzi in Chepstow are 5 Bed Luxury House With Swimming Pool, 5br Luxury House With Swimming Pool Chepstow Town and Court Park Barn.

  • What time of year is best to rent a vacation rental Chepstow?

    Spring and autumn are lovely times to visit Chepstow, with mild weather and fewer crowds. Summer is popular for outdoor activities, but it can get busy. Winter can be chilly, but the town is still charming and there are fewer tourists.

Popular destinations

Best Chepstow holiday rentals with a balcony

Wallhope Escape - Chepstow
No reviews

Wallhope Escape

house, Tidenham
Wallhope Escape, a spacious 3-bedroom house in Tidenham, Gloucestershire, is situated approximately 27 kilometres from Bristol Parkway station, offering easy access to Bristol's attractions.
This 144 square metre property boasts three bathrooms including a hot tub, a fully equipped kitchen, a private terrace with garden views, free Wi-Fi, parking, and accommodates up to eight guests.
Wallhope Retreat - Chepstow
10 4 reviews

Wallhope Retreat

house, Chepstow
Wallhope Retreat is a short distance from Chepstow town centre, just 17km from Bristol Parkway Station and 21km from Cabot Circus. The surrounding area is beautiful, with easy access to cycling trails and the River Wye.
This 2-bedroom house offers a comfortable and spacious stay for up to 4 guests, with a total floor area of 119 square metres. Enjoy the modern amenities, including a fully equipped kitchen, free Wi-Fi, a terrace with garden views, and a hot tub for relaxation.
Oak Tree Cottage, Countryside Retreat With River View - Chepstow
9.1 51 reviews

Oak Tree Cottage, Countryside Retreat With River View

house, Lydney
Oak Tree Cottage is situated in Lydney, Gloucestershire, just 31 kilometres from Bristol Parkway Station and 37 kilometres from Cabot Circus, offering a peaceful escape close to the River Severn.
This two-bedroom house, with a spacious 108 square metres of floor area, is ideal for families, with a fully equipped kitchen, garden, and patio, perfect for enjoying the outdoors.
Exceptional Luxury At Laurel House By Stae-homes - Chepstow
No reviews

Exceptional Luxury At Laurel House By Stae-homes

apartment, Magor
This spacious rural property, a five-bedroom detached house, is located in Redwick, near Magor and Caldicot in South East Wales, offering easy access to Caldicot Castle and Country Park, approximately 4 kilometers away, and the Gwent Levels for scenic walks.
This family-friendly accommodation, suitable for up to 12 guests, features 476 square meters of floor area, a kitchen with an AGA cooker, a heated swimming pool and sauna for summer use, a games room with a snooker table, and extensive private grounds with gardens and parking.

Best pet friendly Chepstow holiday rentals

Among the 67 accommodations in Chepstow, here are the 4 best pet friendly rentals

Cosy Pet Friendly Barn With Fab Views - Chepstow
9.8 131 reviews

Cosy Pet Friendly Barn With Fab Views

bungalow
Dolly's Barn, a pet-friendly bungalow near Chepstow in the Lower Wye Valley Area of Outstanding Natural Beauty, offers stunning countryside views and is conveniently located a short distance from Chepstow's historical sites.
This self-contained cottage features an open-plan kitchen/lounge, a double bedroom, a bathroom with a walk-in shower, and accommodates two guests, boasting a log-burning stove, central heating, an electric car charging point, and solar panels.
The Barn With A View - Chepstow
10 1 review

The Barn With A View

apartment, Portskewett
The Barn, a holiday let in Portskewett, is located 24 kilometres from Bristol Parkway Station and 32 kilometres from Cabot Circus.
This one-bedroom apartment accommodates up to seven guests and offers a private terrace, free WiFi, a kitchen with a fridge and microwave, and private parking.
Luxury Gatehouse On Mathern Palace Estate - Hot Tub - 3 En-suite Bedrooms - Chepstow
10 2 reviews

Luxury Gatehouse On Mathern Palace Estate - Hot Tub - 3 En-suite Bedrooms

cottage, Mathern
This detached property in Mathern is located 1.2 kilometres from St. Pierre Country Club and 800 metres from the Wye Valley.
This 3-bedroom holiday home accommodates up to 6 guests and offers a kitchen with a microwave and dishwasher, a Jacuzzi, and on-site parking.
Sedbury Farm Cottages #3 - Chepstow
9.0 216 reviews

Sedbury Farm Cottages #3

apartment
This self-catering apartment is located in Gloucestershire, just a short drive from the picturesque Cotswolds and within easy reach of Stratford-upon-Avon and Cheltenham. The apartment consistently receives excellent ratings for its cleanliness, location, and overall user experience.
The apartment has two bedrooms and one bathroom, comfortably accommodating up to four guests. It offers a modern interior, a fully equipped kitchen with a fridge, microwave oven, and dishwasher, a garden, parking, and free Wi-Fi.
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