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.

Splendid House Great Location To Wave Surf & South West Water Park - Super Garden By Stae-homes - Chepstow
9.8 4 reviews
Chepstow
21/06 – 23/06
£209/nighttotal: Â£418 (2 )

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

3 2
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.
Oak Tree Cottage - Chepstow
9.0 47 reviews
Chepstow
21/06 – 23/06
£175/nighttotal: Â£350 (2 )

Oak Tree Cottage

2 2
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.
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: Â£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.
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.

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.

Modern 2-bedroom Apartment - Chepstow
8.5 161 reviews
Chepstow
29/08 – 30/08
£194/nightfor 1 night

Modern 2-bedroom Apartment

2 2
apartment , Bristol
This modern two-bedroom flat is located in Bristol, just 3.7 kilometres from Bristol Parkway Station and 9.3 kilometres from Bristol Zoo, in a quiet area convenient for exploring the city. The property has received excellent ratings for cleanliness, user experience, and location, making it a great choice for travellers.
The flat offers 59 square metres of space, comfortably accommodating up to five guests. It comes equipped with a fully fitted kitchen, free Wi-Fi, and parking, as well as a comfortable living room with a flat-screen TV, ensuring a pleasant and convenient stay.
3-bed-patchway-self-check-in-parking-wi-fi-sleeps 5 - Chepstow
Chepstow
24/07 – 27/07
£184/nighttotal: Â£552 (3 )

3-bed-patchway-self-check-in-parking-wi-fi-sleeps 5

1 5
house , Bristol
This detached house in Patchway, Bristol, is situated 4.35 kilometres from Bristol Parkway Station and is 10.62 kilometres from Cabot Circus and Bristol Cathedral.
This 80 square metre property offers 3 bedrooms, 1 bathroom, a garden with barbecue facilities, free private parking, complimentary Wi-Fi, and a shared lounge, accommodating up to 9 guests with self-check-in.
3 Bedroom Home In The Heart Of Caldicot - Chepstow
9.5 8 reviews
Chepstow
21/06 – 23/06
£157/nighttotal: Â£314 (2 )

3 Bedroom Home In The Heart Of Caldicot

1 2
apartment , Monmouthshire
This 3-bedroom flat is located in Caldicot, Monmouthshire, 500 meters from Caldicot Castle and close to local amenities and major transport links.
This property accommodates up to 6 guests and features a fully equipped kitchen with a fridge, freezer, and microwave, along with free Wi-Fi and heating for a comfortable stay.
Modern 3-bed Bradley Stoke Self Check-in Free Parking Fast Wi-fi - Chepstow
Chepstow
29/08 – 30/08
£234/nightfor 1 night

Modern 3-bed Bradley Stoke Self Check-in Free Parking Fast Wi-fi

3 2
apartment , Bradley Stoke
This 3-bedroom detached property in Bradley Stoke is located in a quiet area, a short drive from Woodlands Golf & Country Club and offers convenient access to Aztec West, major motorways, and Bristol Parkway Station.
This comfortable home accommodates up to 5 guests and features super-fast Wi-Fi, free parking, a private garden, and is situated close to parks, walking paths, and local cafés.

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.

Hawthorn View: Bristol Large House Stae-homes - Chepstow
Chepstow
21/06 – 23/06
£194/nighttotal: Â£388 (2 )

Hawthorn View: Bristol Large House Stae-homes

3 2
apartment , Bradley Stoke
This three-bedroom house in Bradley Stoke enjoys a peaceful cul-de-sac location, a short drive (approximately 15 minutes) from Cribbs Causeway shopping centre and the Concorde Museum.
The 95 square metre property offers self-check-in, parking for two cars, a fully equipped kitchen including a dishwasher and Nespresso machine, a garden with patio furniture, and accommodates up to five guests.
Gorgeous 3 Bed House In Bristol - Chepstow
8.1 14 reviews
Chepstow
21/06 – 23/06
£208/nighttotal: Â£416 (2 )

Gorgeous 3 Bed House In Bristol

1 2
house , Bristol
This three-bedroom house near Bristol Parkway station (3km), offers convenient access to Bristol city centre (11-13km) and Bristol Airport (31km).
The 10-square-metre property features a full kitchen, private parking, Wi-Fi, and accommodates up to 11 guests, with a garden and terrace adding to its appeal.
Broad Leaze House - Hopewell - Chepstow
Chepstow
21/06 – 23/06
£133/nighttotal: Â£266 (2 )

Broad Leaze House - Hopewell

2 2
apartment , Bristol
This Patchway flat is ideally located within 1.6km of The Mall at Cribbs Causeway and Aztec West Business Park, and within 4.8km of Wild Place Project and The Wave water park, offering easy access to shopping, business, and family attractions.
This two-bedroom, one-bathroom dwelling sleeps four, boasting a fully equipped kitchen with dishwasher, private balcony, garden access, parking, and a washing machine; perfect for a Bristol getaway.
Betty Shepherd's Hut - Chepstow
10 12 reviews
Chepstow
21/06 – 23/06
£198/nighttotal: Â£396 (2 )

Betty Shepherd's Hut

1 2
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.

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 ∙ 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.
Gardener's Cottage At Mathern Palace - Chepstow
9.3 64 reviews
Chepstow
13/08 – 16/08
£229/nighttotal: Â£687 (3 )

Gardener's Cottage At Mathern Palace

2 4
house , Chepstow
Gardener's Cottage is situated in Chepstow, a charming town just 22 kilometres from Bristol Parkway Station, offering easy access to both the town's attractions and the wider region. The cottage has consistently received excellent ratings for its cleanliness, location, and overall experience.
This two-bedroom cottage comfortably accommodates up to four guests, providing a relaxing retreat for families or groups of friends. Guests can enjoy a peaceful garden, a well-equipped kitchenette, free parking, and complimentary Wi-Fi, making it ideal for a comfortable and enjoyable stay.
Gardeners Cottage At Mathern Palace - Chepstow - Chepstow
10 2 reviews
Chepstow
13/08 – 16/08
£176/nighttotal: Â£528 (3 )

Gardeners Cottage At Mathern Palace - Chepstow

2 4
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 Stable - Chepstow
9.6 253 reviews
Chepstow
21/06 – 23/06
£239/nighttotal: Â£478 (2 )

The Stable

2 2
apartment , Lydney
The Stable is a peaceful apartment located in Lydney, Gloucestershire, just 20 miles from Kingsholm Stadium and 22 miles from Bristol Parkway Station. It has received excellent ratings for its cleanliness, location, and overall experience, making it an ideal choice for travellers seeking a relaxing stay.
The apartment has two bedrooms and one bathroom, offering 105 square metres of living space. It features a fully equipped kitchen, a private garden, free Wi-Fi, and free private parking, making it perfect for families or groups looking for a comfortable and convenient home away from home.
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