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

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 ∙ 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.
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.
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.

Best Chepstow holiday rentals with parking

The Studio - Chepstow
9.7 156 reviews

The Studio

chalet
This studio apartment is located in a peaceful rural area near Chepstow, a 5-minute drive from shops and 40 minutes from Bristol and Cardiff. It has consistently received excellent ratings for location, cleanliness, and overall user experience.
The self-contained annexe has one bedroom and one bathroom, comfortably accommodating two guests. The studio features a spacious lounge with a log burner, a well-equipped kitchen, and a private patio and garden, perfect for enjoying the tranquil surroundings.
The Old Rectory With Swimming Pool - Chepstow
10 4 reviews

The Old Rectory With Swimming Pool

apartment, Bristol
This five-bedroom Bristol house, near Thornbury, is situated 4.8km from Thornbury Castle and Thornbury Golf Centre, offering easy access to family attractions such as Cattle Country Adventure Park and Delta Force Paintball North Bristol (within 14.5km).
The 372 square metre property boasts three bathrooms, a private swimming pool, a garden, parking, and sleeps up to ten guests, complete with a well-equipped kitchen including a fridge and dishwasher.
Carpenters Cottage - Central Chepstow With Parking - Chepstow
9.8 493 reviews

Carpenters Cottage - Central Chepstow With Parking

apartment
Carpenters Cottage, a one-bedroom holiday home in Chepstow, Monmouthshire, is located less than 0.2km from Chepstow Castle and the town centre, and the same distance from pubs along the River Wye.
This recently refurbished, 4-star self-catering property sleeps two guests and boasts a fully equipped kitchen (including a fridge and microwave), garden, parking, and is ideally situated for exploring Chepstow and the wider Monmouthshire area.
Castle House Apartment 2 Georgian Town House - Chepstow
10 87 reviews

Castle House Apartment 2 Georgian Town House

apartment
This charming apartment is situated in a Grade 2 listed Georgian townhouse in the lower part of Chepstow, just a few hundred metres from the River Wye and the medieval Chepstow Castle, offering a peaceful setting within easy reach of the town's attractions. The property has consistently received excellent ratings for its cleanliness, location and overall experience.
The self-contained flat is located on the second floor and comfortably accommodates two guests. It features a well-equipped kitchen, a private garden, parking, and access to a range of local activities, including bike hire, canoeing, beekeeping and guided walks.

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 one of the oldest and most impressive Norman castles in Wales. You'll also want to visit the historic town centre, with its beautiful old buildings and quaint shops. For a bit of nature, head over to the Wye Valley, just a short drive away. It's a stunning area of natural beauty with lots of walking trails.
  • 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 is a brilliant walk, following the ancient border between England and Wales. It's a bit of a trek, but you'll be rewarded with amazing views. For a shorter cycle, try the route along the River Wye. The scenery is beautiful, and it's relatively flat, so it's good for all levels.
  • 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?

    You can go kayaking or canoeing on the River Wye, or try your hand at rock climbing at the nearby The Brecon Beacons National Park. There's also plenty of great walking and cycling in the area, and if you're feeling adventurous, you can even go paragliding. For something a bit more relaxed, there's the Chepstow Golf Club.
  • What are the best holiday rentals with a pool in Chepstow?

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

    You're well-placed to explore the rest of South Wales. Bristol is a vibrant city just an hour away by car, and you can easily reach Cardiff, the capital of Wales, in about an hour and a half. For a more scenic trip, head to the historic town of Monmouth, 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 Wi-Fi, a washing machine, and a TV. Many also have a garden or patio, and some even have a hot tub. Look out for rentals that are pet-friendly if you're bringing your furry friend along.
  • 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?

    It really depends what you're looking for! Summer is the busiest time, but you'll have the best weather for outdoor activities. Spring and autumn are lovely for walking and cycling, and you'll find fewer crowds. Winter can be chilly, but it's a great time to explore the local pubs and restaurants.

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.
Laurel House By Stae-homes - Chepstow
No reviews

Laurel House By Stae-homes

house, Magor
Laurel House in Magor is located 30 kilometres from Bristol Airport and 30 kilometres from key Cardiff landmarks such as the University of South Wales – Cardiff Campus and Motorpoint Arena Cardiff.
This spacious 5-bedroom, 3-bathroom property offers accommodation for up to 23 guests, featuring a kitchen with a dishwasher and microwave, a terrace with pool views, an outdoor swimming pool, complimentary on-site parking, and free WiFi, with activities like cycling and hiking available nearby.
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 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

Special Celebration Country House. 4 Acre Grounds. Pet Friendly! - Chepstow
10 6 reviews

Special Celebration Country House. 4 Acre Grounds. Pet Friendly!

apartment, Woolaston
This six-bedroom, six-bathroom house near Woolaston offers a peaceful rural escape, situated within 10km of Taurus Crafts, the Forest of Dean, and the River Wye.
The 576 square metre property boasts a garden, barbecue, patio, Smart TV, and parking, comfortably accommodating up to 12 guests with amenities including a dishwasher, washing machine and fireplace.
Orchard Cottage Monmouthshire - Chepstow
10 1 review

Orchard Cottage Monmouthshire

house, Saint Arvans
This one-bedroom holiday cottage in Saint Arvans, Monmouthshire, is located approximately 25 kilometres from Bristol Parkway Station and 50 kilometres from Bristol Airport, offering access to Bristol Cathedral and Ashton Court.
This pet-friendly holiday home provides a private garden with a barbecue, a fully equipped kitchen, free WiFi, and is ideal for outdoor pursuits such as golfing, fishing, and cycling.
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.
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.
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