Holiday Rentals in Chepstow

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Chepstow holiday rentals
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67 Holiday Rentals and Airbnb in Chepstow

Best family friendly Chepstow holiday rentals

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

Caradoc - Chepstow
9.3 22 reviews

Caradoc

house, Chepstow
Caradoc is a spacious house in Chepstow, just 11km from Tintern Abbey and 12km from St Briavel's Castle, making it a great base for exploring the area's historical attractions. It has consistently received very good user and location ratings and an excellent cleanliness rating.
The house has 5 bedrooms and 4 bathrooms, spread over 160 square metres, accommodating up to 10 guests. It includes a fully equipped kitchen, a garden, free Wi-Fi, parking, and is pet-friendly, making it perfect for families and groups.
Character Cottage, Stroll To Town, Wye Valley Base - Chepstow
9.9 109 reviews

Character Cottage, Stroll To Town, Wye Valley Base

apartment
Vauxhall Cottage is a charming 1790s property located just 500 metres from Chepstow's historic town centre, putting you within easy reach of the town's attractions, including Chepstow Castle. The cottage has consistently received excellent ratings for location, cleanliness, and overall user experience.
This cosy holiday home can comfortably accommodate up to 6 guests and features a well-equipped kitchen, a comfortable living room with a wood-burning stove, and a sunny garden room. Enjoy the enclosed garden, perfect for relaxing with your furry friends, and take advantage of the modern amenities like a fast Wi-Fi connection, a private study, and a washing machine.
Cottage ∙ 4 Bedrooms ∙ 10 Guests - Chepstow
10 5 reviews

Cottage ∙ 4 Bedrooms ∙ 10 Guests

cottage, Pilning
Hidden Well, a luxurious barn conversion in Aust, South Gloucestershire, offers easy access to the Severn Bridges and is approximately 10km from Pilning, placing guests within reach of Bristol's attractions including the Clifton Suspension Bridge and SS Great Britain.
This three-bedroom property sleeps up to ten guests and boasts a swimming pool, hot tub, and fully equipped kitchen including a dishwasher, alongside a garden perfect for alfresco dining; nearby attractions include the Aust Wetlands and Wild Place Project.
Cottage ∙ 3 Bedrooms ∙ 5 Guests - Chepstow
9.7 36 reviews

Cottage ∙ 3 Bedrooms ∙ 5 Guests

cottage, Woolaston
The Piggery is situated in the Gloucestershire countryside, just off a narrow lane near Woolaston, with stunning views of the River Severn and a good pub and shop within an 800-yard walk.
This 3-bedroom, 5-guest capacity cottage offers a spacious 130 square meter living area, a fully equipped kitchen with a fridge, microwave oven, and dishwasher, and a peaceful garden setting, perfect for families or groups seeking a relaxing retreat.

Best Chepstow holiday rentals with parking

Stone Cottage With A Splendid Wye Valley View - Chepstow
9.9 112 reviews

Stone Cottage With A Splendid Wye Valley View

apartment
This charming cottage is located just a short distance from the village of Brockweir, offering stunning views of the River Wye and the surrounding countryside. It has received excellent ratings for its location, cleanliness, and overall experience.
The cottage has two bedrooms and one bathroom, accommodating up to four guests. It features a well-equipped kitchen, a private balcony and garden, and a wood-burning stove for cosy evenings.
Self-contained Annexe, Chepstow - Chepstow
9.8 71 reviews

Self-contained Annexe, Chepstow

house
This private annexe is located in central Chepstow, just 700 metres from the town centre and close to the racecourse, the Wye Valley, the River Wye, and Chepstow Castle. The property has received excellent ratings for its location, cleanliness, and overall experience.
The annexe is a modern and refurbished one-bedroom self-catering accommodation with an ensuite shower room, sleeping up to two guests. It offers essential amenities like a small fridge, tea and coffee making facilities, a DAB radio, and Wi-Fi access via a personal hotspot. Free on-street parking is available within a 3-minute walk.
Chepstow Apartmentshort Walk To Town&free Parking - Chepstow
10 45 reviews

Chepstow Apartmentshort Walk To Town&free Parking

apartment
This newly renovated one-bedroom flat is situated in a peaceful, upscale residential area of Chepstow, a 5-minute walk from the town centre and within easy reach of the Wye Valley Area of Outstanding Natural Beauty, with Chepstow Castle a short stroll away.
This accommodation offers a private entrance, a king-size bed, a 60-inch smart TV, and a fully equipped kitchen with a dishwasher, providing a comfortable base for exploring local walking trails, historical sites like Tintern Abbey (a short drive/walk), and prestigious golf courses such as St Pierre Golf Club (5 minutes away), while also being conveniently located for grocery shopping at Tesco and M&S Foodhall and travel via Chepstow Train Station.
The Nursery Wing - Wyndcliffe Court - Chepstow
9.9 130 reviews

The Nursery Wing - Wyndcliffe Court

apartment
This apartment is located just off the Wye Valley walk at Upper Wyndcliff, offering easy access to the beautiful scenery of the Wye Valley and nearby towns like Tintern and Chepstow, all within a 10-kilometer radius. It has consistently received excellent ratings for location, cleanliness, and user experience.
The self-catering property has one bedroom and one bathroom, comfortably accommodating up to two guests. Guests can enjoy a modern kitchen, a garden with uneven steps and steep drops, and a relaxing bathroom with a freestanding roll-top bath, all included in the price.

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 Norman castle with a rich history. If you want something a bit different, the Wye Valley is just a short drive away, and it's a beautiful area with lots of walking trails and stunning views. And for something a bit more modern, the Chepstow Racecourse is a great place to catch a horse race.
  • What are the best Airbnb and holiday rentals in Chepstow?

    Broadrock Accommodation - Clock Cottage, Chepstow Town - Welsh Cottage and Sedbury Farm Cottages #2 are among the best Airbnb and holiday rentals in Chepstow.

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

    The Offa's Dyke Path runs right through Chepstow, it's a long-distance trail that follows the border between England and Wales, and there are some great shorter walks you can do right in town. If you're into cycling, the Wye Valley Cycle Path is a great option. It's a traffic-free route that follows the River Wye.
  • 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 is a great place for outdoor activities. You can go kayaking or canoeing on the River Wye, or go for a hike in the Wye Valley. There's also a great golf course at Chepstow Golf Club, and the Chepstow Racecourse hosts horse racing events throughout the year.
  • What are the best holiday rentals with a pool in Chepstow?

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

    Chepstow is well-connected, you can easily get to Bristol, Newport, and Cardiff by car or train. If you're looking for a day trip, Tintern Abbey is a beautiful historic site just a short drive away.
  • 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 will have the basics like a kitchen, bathroom, and bedrooms. But you can also find places with extras like a garden, a patio, or even a hot tub. Many rentals also offer Wi-Fi and parking.
  • What are the best rentals or Airbnbs with a jacuzzi in Chepstow?

    The best holiday 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?

    The best time to visit Chepstow really depends on what you're looking for. If you want to enjoy the warm weather and outdoor activities, then summer is a great time to visit. But if you want to avoid the crowds and enjoy the beautiful autumn colours, then late September or October is a good option.

Popular destinations

Best Chepstow holiday rentals with a balcony

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.
3-4 Bed Barn, Open Living Space , Pet Friendly, Rural, With Easy Access From M4 - Chepstow
10 1 review

3-4 Bed Barn, Open Living Space , Pet Friendly, Rural, With Easy Access From M4

cottage, Usk Monmouthshire
This three-bedroom, three-bathroom holiday home in rural Monmouthshire is situated within 14.5km of Usk Castle and the Wye Valley, offering easy access to other historical sites including Llangibby Motte and Castle, Caerleon Castle, and Raglan Castle.
Sleeping up to 10 guests, the property boasts a full kitchen with dishwasher and washing machine, a terrace, garden, parking, fireplace, Smart TV, and pet-friendly accommodation.
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.
The Nook - Chepstow
10 1 review

The Nook

house, Tidenham
The Nook in Tidenham offers a peaceful countryside escape, situated approximately 27 kilometres from Bristol Parkway station and within easy reach of Bristol's attractions including Bristol Cathedral and Cabot Circus.
This self-catering cottage boasts a 10 square metre floor area, sleeping two guests in one bedroom with one bathroom, a private hot tub, and free Wi-Fi and parking.

Best pet friendly Chepstow holiday rentals

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

The Old Rectory - Chepstow
9.7 3 reviews

The Old Rectory

house, Bristol
The Old Rectory is situated in a peaceful location just 17 kilometres from Bristol Temple Meads Station and 18 kilometres from Bristol Zoo. This charming house offers a tranquil retreat for those seeking a relaxing getaway.
This spacious property comprises 5 bedrooms and 3 bathrooms, providing comfortable accommodation for up to 10 guests. The house comes equipped with a range of amenities, including a fully equipped kitchen, a washing machine, a fireplace, free Wi-Fi, and ample parking.
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.
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.
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.
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