Holiday Rentals in Chepstow

28 available vacation rental offers

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Chepstow holiday rentals
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Best Holiday rentals and Airbnb offers in Chepstow

Explore Holiday Rentals for Families in Chepstow

Getting the holiday rental right makes all the difference for a family trip to Chepstow. Find city attractions within easy reach. Start comparing now.

Bilsham Meadows - Chepstow
10 4 reviews
Chepstow
01/07 – 02/07
£1556/nightfor 1 night

Bilsham Meadows

5 1
apartment , Pilning
This five-bedroom, three-bathroom house in Bilsham Meadows, Aust (approximately 1.6km from a shop and 1.6km from a pub), offers a tranquil farm setting near Pilning.
Sleeping ten guests, the property features an open-plan kitchen-diner-sitting area with modern appliances, a private patio with a hot tub, and a private driveway with an EV charging point (at extra cost); all utilities, including Wi-Fi, are included.
Lushmint&sound - Chepstow
10 1 review
Chepstow
24/07 – 27/07
£221/nighttotal: £663 (3 )

Lushmint&sound

3 5
house , Bristol
LushMint&Sound is a 3-bedroom holiday home in Bristol, located 4.2 kilometres from Bristol Parkway Station and 9.8 kilometres from Clifton, with Cabot Circus and Bristol Cathedral 10.5 kilometres away.
This family-friendly property offers parking, free WiFi, a private garden, two bathrooms, and accommodates up to 10 guests, with a floor area of 12 square meters.
Cottage ∙ 3 Bedrooms ∙ 5 Guests - Chepstow
Chepstow
27/06 – 04/07
£175/nighttotal: £1225 (7 )

Cottage ∙ 3 Bedrooms ∙ 5 Guests

3 2
cottage , Hewelsfield
This pet-friendly barn conversion in Hewelsfield, Wye Valley and Forest of Dean, offers panoramic views and direct access to Offa's Dyke and the Wye Valley Walk, located 2.75 kilometers from the nearest restaurant and 1.6 kilometers from Tintern Abbey.
This luxury cottage sleeps five guests, featuring three bedrooms, two bathrooms with underfloor heating on the ground floor, a dishwasher, Wi-Fi, an enclosed garden with a BBQ, and is ideally situated for exploring nearby attractions like Chepstow Castle and the Forest of Dean.
The Potting Shed At Mathern Palace - Chepstow
9.0 2 reviews
Chepstow
13/08 – 16/08
£205/nighttotal: £615 (3 )

The Potting Shed At Mathern Palace

2 4
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.

Choose the Right Self-Catering Holiday Rentals with Free Parking in Chepstow

Free on-site parking comes with these holiday rentals in Chepstow, allowing you to focus on the city centre from day one.

Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chepstow
9.7 14 reviews
Chepstow
29/08 – 30/08
£421/nightfor 1 night

Cottage ∙ 2 Bedrooms ∙ 4 Guests

2 2
cottage
Top Lodge is a two-bedroom holiday home located in the village of Llanvair-Discoed, 4.3 kilometres from Penhow, Monmouthshire, with easy access to the Wye Valley Area of Outstanding Natural Beauty and the coast.
This 105 square metre cottage offers a peaceful setting with a garden, swimming pool, jacuzzi, and parking, perfect for families or couples seeking a relaxing escape.
Bilsham Meadows - Chepstow
9.6 21 reviews
Chepstow
01/07 – 02/07
£1485/nightfor 1 night

Bilsham Meadows

5 1
house , Bristol
This five-bedroom Bristol house, situated in Bilsham Meadows, is approximately 19 kilometres from Bristol Parkway Station and within easy reach of attractions including Bristol Cathedral and Ashton Court.
The 160 square metre property boasts three bathrooms with walk-in showers and hot tubs, a fully equipped kitchen, a swimming pool, a jacuzzi, a garden, and parking; golfing and cycling are nearby.
Cooks House By Cliftonvalley Apartments - Chepstow
8.7 3 reviews
Chepstow
24/07 – 27/07
£301/nighttotal: £903 (3 )

Cooks House By Cliftonvalley Apartments

3 5
house , Bristol
Cooks House, situated in Clifton Valley, Bristol, offers a quiet residential stay approximately 4.8km from Bristol Parkway Station and 16-18km from central Bristol attractions such as Bristol Temple Meads Station and Bristol Cathedral.
This three-bedroom, three-bathroom property boasts 800 square metres of floor space, comfortably accommodating up to 11 guests, and includes free private parking, free Wi-Fi, a fully equipped kitchen with dishwasher and microwave, a garden, and a washing machine; the Free private parking and private check-in/check-out offer adds convenience.
Spacious 4-bed Home Near Cribbs & Bristol - Chepstow
9.1 7 reviews
Chepstow
08/08 – 10/08
£321/nighttotal: £642 (2 )

Spacious 4-bed Home Near Cribbs & Bristol

4 7
apartment , Patchway
This four-bedroom house in Patchway, Bristol, is situated 4.2 kilometers from The Mall at Cribbs Causeway and offers convenient access to Patchway train station, which provides direct links to Bristol city centre.
This residence accommodates up to eight guests with two and a half bathrooms, including an ensuite, a fully equipped kitchen with a fridge and microwave oven, and on-site parking, with attractions like Aerospace Bristol and Blaise Castle within easy reach.

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, a huge Norman fortress with a fascinating history. You can also visit the Tintern Abbey, a beautiful ruined abbey just outside Chepstow, and the National Trust property, The 18th-century Piercefield House and Gardens, with its stunning views across the Wye Valley.
  • 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 Wye Valley Walk is a popular route that takes you through some of the most beautiful scenery in the area. For cyclists, the Forest of Dean is a great place to explore, with plenty of off-road trails.
  • 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, play golf at the Chepstow Golf Club, or go horse riding in the surrounding countryside. There are also plenty of opportunities for fishing, hiking, and mountain biking.
  • What are the best holiday rentals with a pool in Chepstow?

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

    You can easily get to Bristol and Cardiff by car or train. The Forest of Dean is also 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 offer Wi-Fi, parking, and bedding. Many also have kitchen facilities, washing machines, and TVs. Some may even have gardens or balconies.
  • 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 is during the spring or autumn, when the weather is mild and the crowds are smaller. Summer can be busy and hot, while winter can be cold and wet.

Destinations nearby

Best Self-Catering Holiday Rentals with a Terrace in Chepstow

Choosing a holiday rental in Chepstow with a private balcony offers city skyline views that are worth every penny. Compare options and find yours.

Laurel Cottage By Stae-homes - Chepstow
Chepstow
24/07 – 27/07
£205/nighttotal: £615 (3 )

Laurel Cottage By Stae-homes

2 5
apartment , Redwick
This Gwent Levels cottage near Redwick, southeast Wales, is situated approximately 6 kilometres from Severn Tunnel Junction station and a short drive from Newport, offering direct access to the Wales Coast Path for walks and bird-watching, with Caldicot Castle and Country Park nearby.
This 80 square metre, two-bedroom, two-bathroom holiday let accommodates up to five guests and features a kitchen with a coffee machine, an enclosed garden, and free parking for three vehicles, with pets welcome.
2 Bed Barn, Open Living Space , Pet Friendly, Rural, With Easy Access From M4 - Chepstow
10 3 reviews
Chepstow
24/07 – 27/07
£204/nighttotal: £612 (3 )

2 Bed Barn, Open Living Space , Pet Friendly, Rural, With Easy Access From M4

2 5
apartment , Usk Monmouthshire
This Monmouthshire holiday home is situated in a peaceful rural setting, within 14.5km of Usk Castle and the Wye Valley, offering easy access to other historic castles including Llangibby Motte and Castle, Caerleon Castle, and Raglan Castle.
The 120 square metre property boasts two bedrooms, two bathrooms, sleeps six guests, and includes a fully equipped kitchen, private balcony, fireplace, free WiFi, and ample parking.
Welsh Gatehouse, Historic Castle Which Can Cater For Electric Vehicle - Chepstow
9.4 58 reviews
Chepstow
01/07 – 02/07
£315/nightfor 1 night

Welsh Gatehouse, Historic Castle Which Can Cater For Electric Vehicle

1 1
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.
Nj&c Properties - Chepstow
9.3 4 reviews
Chepstow
29/08 – 30/08
£115/nightfor 1 night

Nj&c Properties

2 2
apartment , Bristol
This Bristol flat is located 2.3 kilometres from Bristol Parkway Station, 5.9 kilometres from Clifton, and 6.3 kilometres from Cabot Circus and Bristol Cathedral.
This soundproofed two-bedroom, one-bathroom apartment accommodates up to seven guests and features a private terrace, free WiFi, private parking, and a kitchen with a microwave and oven.

Popular Pet-Friendly Holiday Rentals in Chepstow

Bringing your dog to Chepstow? These holiday rentals are perfectly set up with dog parks nearby and city walks on the doorstep.

Cottage ∙ 1 Bedroom ∙ 2 Guests - Chepstow
9.7 2 reviews
Chepstow
27/06 – 04/07
£71/nighttotal: £497 (7 )

Cottage ∙ 1 Bedroom ∙ 2 Guests

1 2
cottage
The Foxes Den Shepherds Hut, a self-catering studio in Shepperdine, Gloucestershire, is 7km from Oldbury-on-Severn, offering easy access to Thornbury and Bristol, with the Cotswolds Area of Outstanding Natural Beauty nearby for walking and cycling.
This 90 square metre dwelling features a double bed, fully equipped kitchen, dining area, Smart TV, modern shower room, and a spacious garden with decking, lawn, and summerhouse; sleeping up to two guests.
3 Bedroom Accommodation In Devauden, Near Chepstow - Chepstow
9.8 10 reviews
Chepstow
24/07 – 27/07
£374/nighttotal: £1122 (3 )

3 Bedroom Accommodation In Devauden, Near Chepstow

3 5
cottage , Devauden, near Chepstow
This three-bedroom, three-bathroom cottage near Chepstow, in Devauden, boasts stunning Vale of Usk views and is situated 11km from shops and 1.6km from local pubs and restaurants.
The self-catering property, part of a barn conversion, sleeps six guests and features an open-plan living area with a fully equipped kitchen, dishwasher, Freeview TV, and a private enclosed courtyard with barbecue; private parking for two cars is also available.
Offas Dyke Cabin - Chepstow
9.5 141 reviews
Chepstow
01/07 – 02/07
£89/nightfor 1 night

Offas Dyke Cabin

1 1
cabin , Sedbury
Offas Dyke Cabin is situated in the countryside near Sedbury, just a 5-minute drive from Chepstow town centre and a short walk from the local village pub. This peaceful location offers easy access to the historic Offas Dyke Path, a scenic walking trail.
The cabin offers a comfortable stay for up to 4 guests with a double bed and two single beds. Guests can enjoy the views of the Severn Estuary and the Severn Bridge from the large outdoor dining space, while amenities like a microwave, kettle, and toaster make self-catering a breeze.
Spacious Cottage, Sunny Garden, Stroll To Town - Chepstow
9.9 103 reviews
Chepstow
29/08 – 30/08
£1688/nightfor 1 night

Spacious Cottage, Sunny Garden, Stroll To Town

1 2
apartment , Chepstow
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.
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