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

The Pink Cottage - Chepstow
9.8 81 reviews

The Pink Cottage

apartment
This recently refurbished fisherman's cottage in Chepstow, Monmouthshire, is a short walk (less than 1 km) from the River Wye and Chepstow Castle.
Sleeping up to eight guests, the three-bedroom property boasts a living room, dining room, kitchen with dishwasher, family bathroom, boot room, west-facing courtyard garden, parking, and Wi-Fi; its location offers easy access to Offa's Dyke Path and the Wales Coast Path.
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.
Cottage ∙ 1 Bedroom ∙ 2 Guests - Chepstow
No reviews

Cottage ∙ 1 Bedroom ∙ 2 Guests

cottage, Brockweir
Ferryman's Lodge, an idyllic wooden lodge, is situated on the outskirts of Brockweir village, offering countryside views and direct access to walks within the Wye Valley National Landscape, with Chepstow a short drive away. This family-friendly cottage for two features an open-plan living space with a woodburning stove, a double bedroom with an en-suite, a kitchen with a fridge and microwave oven, and a garden with a raised veranda, all within easy reach of Brockweir's pubs, convenience store, and riverside.
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.

Best Chepstow holiday rentals with parking

Gardeners Cottage At Mathern Palace - Chepstow - Chepstow
10 2 reviews

Gardeners Cottage At Mathern Palace - Chepstow

cottage, Chepstow
This Chepstow holiday home is situated 1.3km from St Pierre Country Club, 3km from Chepstow Castle, and 5km from Chepstow Racecourse, offering easy access to local attractions.
Sleeping four guests in two bedrooms and one bathroom, the self-catering property includes a fully equipped kitchen with fridge, microwave, oven and washing machine, plus a Smart TV and peaceful garden with parking.
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.
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.
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.

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

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.
Sedbury Farm Cottages - Chepstow
No reviews

Sedbury Farm Cottages

apartment, Chepstow
Apartment listing. This accommodation is based in Chepstow.
Facilities and services include a garden, a fridge and a dish washer. Take advantage of the terrace in this apartment in Chepstow.
Broadrock Accommodation - Clock Cottage - Chepstow
9.7 152 reviews

Broadrock Accommodation - Clock Cottage

apartment, Chepstow
This apartment is located in Chepstow, within the Wye Valley, a 40-minute drive from Bristol and Cardiff. It's rated excellent for location, cleanliness, and user experience, making it a great choice for travellers.
The apartment is self-catering, with a kitchen equipped with a fridge, microwave, and dishwasher. It also has a terrace or balcony, a garden, a restaurant, a fitness centre, a tennis court, parking, and internet access.
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

9 Bed Home Designed For Contractors And Families - Chepstow
10 3 reviews

9 Bed Home Designed For Contractors And Families

apartment, Patchway
This nine-bedroom house in Patchway, Bristol, offers convenient access to Blaise Castle Estate Country Park, with its proximity to major attractions such as Ashton Gate Stadium and the Memorial Stadium (distances unspecified).
The property sleeps nine, features three bathrooms, Wi-Fi, and a dryer, making it ideal for large families or contractors, and provides a comfortable home-from-home experience.
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.
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.
Laurel Retreat- A Relaxing And Beautiful Rural Retreat By Stae-homes - Chepstow
No reviews

Laurel Retreat- A Relaxing And Beautiful Rural Retreat By Stae-homes

house, Magor
Laurel Retreat, a spacious house in Magor, is located 31 kilometers from the University of South Wales – Cardiff Campus and Motorpoint Arena Cardiff.
This property offers 7 bedrooms, 5 bathrooms, and accommodates up to 32 guests, featuring a kitchen with a fridge, microwave oven, and dishwasher, an outdoor swimming pool, a sauna, a garden, terrace, and free private parking.
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