Holiday Rentals in Chepstow

67 available vacation rental offers

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Chepstow holiday rentals
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Best family friendly Chepstow holiday rentals

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

New 3 Bedroom Apartment Next To Station - Chepstow
9.0 11 reviews

New 3 Bedroom Apartment Next To Station

apartment, Chepstow
This 3-bedroom flat in Moffat offers convenient access to golf clubs, with Dumfries and County Golf Club 38.6 kilometres away and Dumfries and Galloway Golf Club 40.2 kilometres distant.
This apartment provides free WiFi, a fully equipped kitchen, and parking, accommodating up to 11 guests with a peaceful setting ideal for relaxation.
Cottage ∙ 5 Bedrooms ∙ 9 Guests - Chepstow
No reviews

Cottage ∙ 5 Bedrooms ∙ 9 Guests

cottage, Woolaston
14 Birchwood Road, a detached holiday home in Woolaston, Gloucestershire, offers convenient access to historical sites such as Tintern Abbey (approximately 8km away) and Chepstow Castle (approximately 11km away).
This five-bedroom house sleeps nine guests and features a spacious kitchen with dishwasher and fridge, a utility room with washing machine and tumble dryer, a dining room, a sitting room with wood-burning stove, an enclosed garden, and ample off-road parking.
Tranquil Cottage Forest Of Dean - Chepstow
10 137 reviews

Tranquil Cottage Forest Of Dean

apartment
This charming one-bedroom cottage is located in Alvington, just 2 kilometers from Lydney Harbour and within easy reach of attractions like Tintern Abbey, Go Ape, and the Forest of Dean Railway. The cottage consistently receives excellent ratings for its cleanliness, location, and overall experience, making it a popular choice for travelers.
The cottage comfortably accommodates two guests, with a sofa bed in the sitting room providing additional sleeping space. It features a fully equipped kitchen, a private enclosed garden, and amenities like a washing machine, clothesline, and tumble dryer. Guests can enjoy nature walks, cycling trails, and explore nearby dog-friendly pubs.
Sedbury Farm Cottages - Chepstow
8.4 125 reviews

Sedbury Farm Cottages

apartment, Chepstow
Sedbury Farm Cottages offers a self-catering apartment in Chepstow, approximately 24 kilometres from Bristol Parkway Station and 31 kilometres from Cabot Circus in Bristol, close to Chepstow town centre and its historic attractions.
This family-friendly property features a private patio, free Wi-Fi, free parking, a fully equipped kitchen with dishwasher, a comfortable seating area with flat-screen TV, and a private bathroom; a relaxing garden is also available for guest use.

Best Chepstow holiday rentals with parking

Betty Shepherd's Hut - Sleeps 2 Guests  In 1 Bedroom - Chepstow
10 14 reviews

Betty Shepherd's Hut - Sleeps 2 Guests In 1 Bedroom

cabin, Forest of Dean
Betty, a charming shepherd's hut, is located on the Lydney Park Estate in the Forest of Dean, a short distance from the picturesque town of Lydney and within easy reach of the Wye Valley. It has received excellent user ratings, making it a popular choice for travellers. The cabin features a compact layout, spanning 20 square metres and comfortably accommodating two guests. Betty boasts a well-equipped kitchenette, a private decking area with a fire pit, and a stylish shower room, offering a blend of rustic charm and modern amenities.
Mediaeval Cellar In The Forest Of Dean - Chepstow
9.8 18 reviews

Mediaeval Cellar In The Forest Of Dean

apartment, Tidenham
This one-bedroom flat is located in the historic village of Tidenham, just 8 kilometres from Chepstow and the Severn Bridge, in the beautiful Wye Valley. The village is steeped in history, with a range of local pubs, shops and attractions to explore.
The self-contained flat is situated in the cellar of a historic cottage, offering a peaceful retreat for up to four guests. The flat has a fully equipped kitchen, a lounge with Sky TV, fast WiFi, a private outdoor seating area with a fire pit and views across the fields.
Betty Shepherd's Hut - Chepstow
9.8 13 reviews

Betty Shepherd's Hut

house, Lydney
Betty Shepherd's Hut, a self-catering cottage in Lydney, Gloucestershire, is situated approximately 34-47km from various Bristol landmarks including Bristol Temple Meads railway station, Ashton Gate Stadium, and Cabot Circus.
This one-bedroom holiday home offers 20 square metres of space, sleeping up to three guests and boasting a private patio, garden, free Wi-Fi, parking, and proximity to Forest of Dean's cycling and hiking trails.
Cottage With Views Over Chepstow Bridge - Chepstow
10 4 reviews

Cottage With Views Over Chepstow Bridge

cottage
This newly renovated cottage, located in Tutshill, Great Britain, offers a prime position at the foot of the Wye Valley, providing views of Chepstow Bridge and Chepstow Castle, and is a 2-minute walk to Chepstow's restaurants and pubs.
This 3-bedroom, 1-bathroom holiday home accommodates up to 5 guests and is ideal for dog owners and walkers, with pets welcome and direct access to numerous routes from the property, plus hosts Paul and Liz live next door for assistance.

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 right on the banks of the River Wye. The town itself has some charming historic buildings, like the 15th century St. Mary's Church. If you're looking for something a little different, the nearby Tintern Abbey is a beautiful ruined abbey with stunning views.
  • What are the best Airbnb and vacation rentals in Chepstow?

    Chepstow Town - Welsh Cottage, Sedbury Farm Cottages #2 and Peaceful - Rural Apartment With River Views 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 is a classic long-distance trail that runs right through Chepstow. For a shorter walk, you can explore the Wye Valley Walk, which takes you along the river and through some lovely countryside. If you're into cycling, the Severn Estuary Trail is a great option, offering stunning views of the river.
  • 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 is famous for its National Hunt racing. The River Wye is great for kayaking, canoeing, and paddleboarding. There's also some great mountain biking trails in the Forest of Dean, just a short drive away.
  • What are the best vacation rentals with a pool in Chepstow?

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

    You can easily reach Bristol by car or train, it's about a 45-minute drive. Monmouth, a charming market town, is just a short drive away, and you can also reach Newport in about 30 minutes by car.
  • What are the best rentals for families and kids in Chepstow?

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

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

    Most vacation rentals in Chepstow will have basic amenities like Wi-Fi, a kitchen, and a bathroom. Many also offer things like a garden, parking, and a washing machine.
  • 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?

    The best time to visit Chepstow is during the spring or autumn, when the weather is mild and the crowds are smaller. You'll be able to enjoy the outdoors without the summer heat and humidity.
  • What are the local dishes in Chepstow region?

    The local area is known for its fresh seafood, especially salmon and trout from the River Wye. You'll also find plenty of traditional Welsh dishes like Welsh lamb and Cawl, a hearty vegetable stew. Don't forget to try the local cider!

Popular destinations

Best Chepstow holiday rentals with a balcony

Large Modern Home, Free Parking, Families And Contractors Welcome - Chepstow
8.6 13 reviews

Large Modern Home, Free Parking, Families And Contractors Welcome

house, Bristol
This spacious Bristol house is situated 4.3km from Bristol Parkway Station and 11km from Clifton, offering easy access to both the station and the Clifton Suspension Bridge.
The 95 square metre property sleeps up to 11 guests in three bedrooms, two bathrooms, and boasts free Wi-Fi, parking, a garden, and a fully equipped kitchen including a microwave and dishwasher.
Sedbury Farm Cottages - Chepstow
No reviews

Sedbury Farm Cottages

apartment, Chepstow
Vacation rental. Your accommodation will be based in Chepstow.
Services and facilities: free parking, a terrace and a dish washer.
Splendid House Great Location To Wave Surf & South West Water Park - Super Garden By Stae-homes - Chepstow
8.9 9 reviews

Splendid House Great Location To Wave Surf & South West Water Park - Super Garden By Stae-homes

house, Bristol
Hawthorn View, a three-bedroom house in a peaceful Bristol suburb, is located 5km from Bristol Parkway Station and within a 16-29km radius of Cabot Circus, Bristol Temple Meads, Bristol Cathedral, and Bristol Airport.
This 95 square metre property offers a private garden, free Wi-Fi, parking, and sleeps seven guests comfortably, with two bathrooms and a fully equipped kitchen including a fridge and microwave.
Welsh Gatehouse A Historic Castle Retreat That Welcomes Dogs And Electric Vehicles - Chepstow
9.5 47 reviews

Welsh Gatehouse A Historic Castle Retreat That Welcomes Dogs And Electric Vehicles

house, Mathern
Welsh Gatehouse is a charming cottage located in Mathern, just 23 kilometres from Bristol Parkway Station, offering a peaceful escape from the city. The property has received excellent ratings for its location, cleanliness, and overall experience.
The cottage provides comfortable accommodation for two guests, with one bedroom, one bathroom, and a floor area of 32 square metres. It features a well-equipped kitchen, a private garden with views, a balcony, and parking.

Best pet friendly Chepstow holiday rentals

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

Chepstow, Forest Of Dean | Sleeps 4 | Dog Friendly - Chepstow
9.8 174 reviews

Chepstow, Forest Of Dean | Sleeps 4 | Dog Friendly

apartment
This charming cottage is located on the edge of the quiet village of Tutshill, just 2km from Chepstow and a short drive from the Forest of Dean. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The two-bedroom cottage can comfortably accommodate four guests and up to three dogs. Enjoy modern conveniences like a fully equipped kitchen, a roll-top bath, and a wood burner, while also taking advantage of the enclosed patio area and the nearby walking and cycling trails.
The Dairy - Chepstow
9.8 174 reviews

The Dairy

apartment
This charming stone cottage is located just a short walk from Tintern Abbey and its pubs and restaurants, and is situated within the peaceful Gloucestershire countryside, just 3 km from the Forest of Dean. The cottage features a unique upside-down design, with a double bedroom and shower room on the ground floor and an open-plan living area and fully equipped kitchenette on the first floor, and can accommodate up to 2 guests. The cottage has a private garden, a sunny gravelled courtyard, and parking, and is perfect for exploring the surrounding area, with easy access to the Offa's Dyke Path, and is pet-friendly.
Bryn Cosyn - Chepstow
No reviews

Bryn Cosyn

apartment, Shirenewton
Bryn Cosyn apartment in Shirenewton offers a self-catering flat for up to three guests, conveniently located approximately 29 kilometres from Bristol Parkway Station and within 35-42 kilometres of Bristol city centre attractions including Cabot Circus, Clifton, Ashton Court, Bristol Temple Meads Station, and Bristol Cathedral.
This one-bedroom, one-bathroom dwelling includes free private parking, Wi-Fi, a fully equipped kitchen with washing machine, and provides towels and bed linen; enjoying a 4-star rating.
Charming, Historic Farm Cottage In The Wye Valley - Chepstow
9.9 29 reviews

Charming, Historic Farm Cottage In The Wye Valley

apartment
This charming cottage is situated on a 23-acre working farm in the southern Wye Valley, just a short drive from the picturesque village of Woolaston. The cottage is located close to the Forest of Dean, offering easy access to hiking trails and cycling routes.
The cottage sleeps up to four guests in two double bedrooms, one of which is located on the ground floor. The cottage is fully equipped with a modern kitchen, a cosy lounge with a log burner, and two bathrooms. The cottage is also fully accessible for wheelchair users and is ideal for families with pets.
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