Holiday Rentals in Chepstow

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Chepstow holiday rentals
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28 Holiday Rentals and Airbnb in Chepstow

Orchard Gate Apartments From Your Stay Bristol - Chepstow
8.3 323 reviews
Chepstow
01/07 – 31/07
NZ$347/nighttotal: NZ$10410 (30 )

Orchard Gate Apartments From Your Stay Bristol

2 3
apartment, Bristol
The Orchard Gate Apartments are situated in a peaceful suburban area just outside Bristol, a 15-minute drive from the city centre and half a mile from the M5 motorway. These apartments have received very good ratings for location, cleanliness, and overall user experience.
The apartments offer comfortable lounges with a sofa, TV, and CD player, perfect for relaxing after a day of exploring. The accommodation comes with fully equipped kitchens, free Wi-Fi, and on-site parking (subject to availability).
Cottage ∙ 5 Bedrooms ∙ 9 Guests - Chepstow
Chepstow
19/08 – 26/08
NZ$423/nighttotal: NZ$2961 (7 )

Cottage ∙ 5 Bedrooms ∙ 9 Guests

5 4
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.
Modern Apartment Near The Wave & Aztec West - Chepstow
9.7 391 reviews
Chepstow
19/08 – 26/08
NZ$251/nighttotal: NZ$1757 (7 )

Modern Apartment Near The Wave & Aztec West

1 4
apartment, Almondsbury
This studio apartment is located on the outskirts of Almondsbury, just 1 kilometre from The Wave water park and within easy driving distance of other attractions like The Wild Place, Cribbs Causeway shopping mall, and Aztec West Business Park. It has received excellent ratings for location, cleanliness, and user experience.
The self-contained studio features a private garden, a kitchen with a fridge, oven, and microwave, and a separate room with a washing machine and heated airer. Guests can enjoy ample parking, access to local footpaths, and the option of adding a single bed in the main bedroom or using the sofa bed in the lounge for shorter stays.
The Willow - Studio 30 - Chepstow
8.4 8 reviews
Chepstow
21/08 – 30/08
NZ$177/nighttotal: NZ$1593 (9 )

The Willow - Studio 30

1 2
studio, Bristol
The Willow - Studio 30 is a self-contained apartment in Bristol, situated 6 kilometres from Bristol Parkway station and within a 16-22 kilometre radius of Cabot Circus, Bristol Temple Meads, Bristol Cathedral, and Ashton Court.
This one-bedroom apartment sleeps two guests and features a fully equipped kitchen with a fridge and microwave, free Wi-Fi, and a TV; nearby public transport provides easy access to Bristol's attractions.
The Elements Residence - Chepstow
Chepstow
01/07 – 02/07
NZ$2123/nightfor 1 night

The Elements Residence

10 1
apartment, Chepstow
This luxury residence in Chepstow offers a secluded setting within a walled garden, located just 500 meters from the town centre and Chepstow railway station, with Chepstow Castle and riverside walks also within easy reach.
This versatile property, ideal for groups, accommodates up to 26 guests across 10 bedrooms and 8 bathrooms, featuring a large kitchen, spacious living areas, and private parking for 4 vehicles, with additional free parking available.
Mackie House By Cliftonvalley Apartments - Chepstow
10 14 reviews
Chepstow
01/07 – 31/07
NZ$474/nighttotal: NZ$14220 (30 )

Mackie House By Cliftonvalley Apartments

3 3
house, Bristol
Mackie House by Cliftonvalley Apartments is located in Bristol, just 2.1 kilometers from Bristol Parkway Station and offers easy access to both Bristol Zoo (7.2 kilometers) and Cabot Circus (9.8 kilometers). This home has received excellent ratings for its location, cleanliness, and user experience.
This 3-bedroom house is 110 square meters and can accommodate up to 5 guests. The house includes a fully equipped kitchen, a private garden, free Wi-Fi, and free private parking, as well as comfortable amenities like towels and bed linen.
Old Ferry View - Chepstow
9.4 234 reviews
Chepstow
21/08 – 30/08
NZ$225/nighttotal: NZ$2025 (9 )

Old Ferry View

1 2
apartment, Bristol
Old Ferry View is a peaceful apartment located in Bristol, about 9.3 miles from Bristol Parkway Station and 13 miles from Bristol Zoo, offering a tranquil escape from the city centre. It has received excellent ratings for its location, cleanliness, and overall user experience.
This one-bedroom flat, with a floor area of 10 square metres, can accommodate up to four guests. The apartment features a fully equipped kitchenette with a microwave, air conditioning, a private patio, complimentary Wi-Fi, parking, and a shuttle service for exploring the city and surrounding areas.
The Old Rectory With Swimming Pool - Chepstow
9.8 28 reviews
Chepstow
27/06 – 04/07
NZ$1329/nighttotal: NZ$9303 (7 )

The Old Rectory With Swimming Pool

1 2
apartment, Oldbury-upon-Severn
This five-bedroom country house near Oldbury-on-Severn, Gloucestershire, offers a tranquil escape less than 60km from Bath and 45km from Bristol.
Sleeping up to ten guests, the property boasts a heated swimming pool (open May-September), tennis court, two acres of private gardens, a well-equipped kitchen, and ample parking.
14 Birchwood Road - Chepstow
10 2 reviews
Chepstow
19/08 – 26/08
NZ$443/nighttotal: NZ$3101 (7 )

14 Birchwood Road

5 4
apartment, Woolaston
This five-bedroom detached house in Woolaston, located at 14 Birchwood Road, is situated just 3 kilometers from the Forest of Dean and offers convenient access to local amenities.
This property accommodates up to nine guests and includes a fully equipped kitchen, a utility room with laundry facilities, a sitting room with a wood-burning stove, and an enclosed garden, with WiFi and parking provided.
Altohaus | Luxury | 4 Bed | Contractors | Groups - Chepstow
8.0 3 reviews
Chepstow
01/07 – 31/07
NZ$347/nighttotal: NZ$10410 (30 )

Altohaus | Luxury | 4 Bed | Contractors | Groups

1 3
apartment, Patchway
This four-bedroom house in Patchway, Bristol offers convenient access to Eastgate Retail Park and benefits from excellent public transport links.
Sleeping up to eight guests, the property includes two bathrooms, a fully equipped kitchen with fridge and freezer, free on-street parking, and free Wi-Fi; long-term booking discounts are available.
New 3 Bedroom Flat Close To Station - Chepstow
10 9 reviews
Chepstow
28/06 – 30/06
NZ$422/nighttotal: NZ$844 (2 )

New 3 Bedroom Flat Close To Station

3 2
apartment, Chepstow
This three-bedroom, three-bathroom apartment in Chepstow offers convenient access to Chepstow train station and is approximately 42 kilometres from Bristol Airport.
The 60 square metre self-catering flat sleeps up to 11 guests and includes free Wi-Fi, on-site parking, a fully equipped kitchenette with oven and microwave, and a washing machine; towels and linen are provided.
Woods Cottage - Chepstow
10 2 reviews
Chepstow
24/07 – 25/07
NZ$1628/nightfor 1 night

Woods Cottage

3 4
house, Usk
Woods Cottage, situated in Usk, Monmouthshire, offers easy access to Bristol and Cardiff, approximately 40-47 km away.
This three-bedroom house, boasting 130 square metres of floor space, provides comfortable accommodation for up to nine guests and features a jacuzzi, garden, parking, and a fully equipped kitchen with dishwasher; free Wifi is also available.

Best family friendly Chepstow holiday rentals

Among the 28 accommodations in Chepstow, here are the 4 best family friendly rentals

Modern 5 Bed House New - Chepstow
10 4 reviews
Chepstow
19/08 – 26/08
NZ$461/nighttotal: NZ$3227 (7 )

Modern 5 Bed House New

5 4
house, Bristol
This spacious 5-bedroom modern house is situated in Bristol, 7.1 kilometres from Bristol Parkway Station and 8.4 kilometres from Clifton, providing convenient access to Bristol Cathedral and Cabot Circus.
This family-friendly property offers accommodation for up to 19 guests with 110 square meters of floor area, featuring a shared kitchen with a fridge, microwave oven, and dishwasher, alongside free private parking and WiFi for a comfortable stay.
Landau House - Chepstow
8.1 18 reviews
Chepstow
27/06 – 04/07
NZ$445/nighttotal: NZ$3115 (7 )

Landau House

2 2
apartment, Bristol
Landau House, a family-friendly apartment in Bristol, is situated a short drive from Bristol Parkway station and further from central Bristol attractions such as Bristol Temple Meads and Bristol Cathedral.
This 50 square metre flat offers two bedrooms, one bathroom, sleeps five guests, and includes free private parking, Wi-Fi, and a fully equipped kitchenette; a nearby coffee shop adds convenience.
Baker's Bun | Sleeps 7 | Spacious Home | Parking & - Chepstow
10 1 review
Chepstow
08/08 – 10/08
NZ$754/nighttotal: NZ$1508 (2 )

Baker's Bun | Sleeps 7 | Spacious Home | Parking &

4 7
apartment, Bradley Stoke
This 4-bedroom house in Bradley Stoke offers convenient access to Bristol, located 8 kilometers away, and is close to major business parks and transport links.
This family-friendly property accommodates up to 7 guests with a fully equipped kitchen, a garden with a pond, a conservatory, and private parking, making it suitable for leisure and business stays.
Modern 2 Bed Home|bristol |Free Parking|nr Parkway - Chepstow
9.8 101 reviews
Chepstow
01/07 – 31/07
NZ$329/nighttotal: NZ$9870 (30 )

Modern 2 Bed Home|bristol |Free Parking|nr Parkway

1 3
apartment, Stoke Gifford
This modern house in Stoke Gifford is less than 1.5km from Bristol Parkway station, providing easy access to Bristol city centre, the M4 & M5 motorways, UWE, Airbus, and MOD.
The two-bedroom property sleeps three, features a well-equipped kitchen, private garden, free parking, and a living room with a smart TV (Netflix & Amazon Prime compatible), plus family-friendly amenities including children's books and proximity to a play park.

Best Chepstow holiday rentals with parking

14 Birchwood Road - Chepstow
8.5 2 reviews
Chepstow
19/08 – 26/08
NZ$453/nighttotal: NZ$3171 (7 )

14 Birchwood Road

5 4
house, Lydney
This five-bedroom, two-bathroom house at 14 Birchwood Road, Lydney, Gloucestershire, is conveniently located approximately 32 kilometres from Bristol Parkway Station and offers easy access to Bristol's attractions, including Cabot Circus, within a 40-kilometre radius.
The 160-square-metre property boasts a fully equipped kitchen with a dishwasher, free Wi-Fi, private parking, a garden, and comfortably accommodates up to 17 guests, making it ideal for family gatherings or group getaways near Lydney's golfing, cycling, and fishing opportunities.
Charming 4-bedroom Cottage In Historic Chepstow - Chepstow
10 3 reviews
Chepstow
19/08 – 26/08
NZ$754/nighttotal: NZ$5278 (7 )

Charming 4-bedroom Cottage In Historic Chepstow

4 4
cottage, Chepstow
Vauxhall Cottage, a 1790s property in Chepstow, is a 5-minute walk from the town centre, Chepstow Racecourse, and offers easy access to the Wye Valley and Forest of Dean.
This three-bedroom, two-bathroom holiday home boasts 168 square metres of space, including a large kitchen with dishwasher, a cosy lounge with log burner, a private study with Wi-Fi, and an enclosed garden with BBQ, accommodating up to six guests and offering off-road parking for 2-3 cars.
The Old Blacksmiths - Chepstow
9.6 14 reviews
Chepstow
24/07 – 25/07
NZ$555/nightfor 1 night

The Old Blacksmiths

2 4
house, Thornbury
The Old Blacksmiths, a 2-bedroom house in Thornbury, South Gloucestershire, is conveniently located 21km from Bristol city centre, offering easy access to the M5 motorway (Junction 14) and attractions such as Bristol Cathedral and Cabot Circus.
This 150 square metre property boasts two bathrooms, sleeps up to 11 guests, includes a fully equipped kitchen with dishwasher, and features a garden, free Wi-Fi, and ambient, soundproofed rooms with parquet floors and a fireplace.
Stylish 2 Bed House - Chepstow
10 2 reviews
Chepstow
01/07 – 31/07
NZ$314/nighttotal: NZ$9420 (30 )

Stylish 2 Bed House

2 3
apartment, Filton
This two-bedroom terrace flat in Filton offers convenient access to local amenities and transport links, situated within a well-connected district.
This apartment sleeps four guests and features a private driveway, a spacious living room with a smart TV, and a private garden, ideal for both business and leisure stays.

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.

Destinations nearby

Best Chepstow holiday rentals with a balcony

The Nook - Chepstow
10 1 review
Chepstow
28/06 – 30/06
NZ$636/nighttotal: NZ$1272 (2 )

The Nook

1 2
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.
4 Bed Luxury Home, Sauna, Hot Tub, Sleeps 9 - Chepstow
10 1 review
Chepstow
08/08 – 10/08
NZ$1479/nighttotal: NZ$2958 (2 )

4 Bed Luxury Home, Sauna, Hot Tub, Sleeps 9

1 7
house, Chepstow
This Chepstow dwelling is situated 21 kilometres from Bristol Parkway Station and within 29 kilometres of Bristol's Cabot Circus and Clifton.
This 30 square metre holiday home offers accommodation for 9 guests, featuring a kitchen with a dishwasher and oven, a private sauna, a hot tub, and a terrace with garden views.
Baker's Bun - Sleeps 7 - Spacious Home - Parking & Garden - Bradley Stoke Bristol - Chepstow
Chepstow
27/06 – 04/07
NZ$399/nighttotal: NZ$2793 (7 )

Baker's Bun - Sleeps 7 - Spacious Home - Parking & Garden - Bradley Stoke Bristol

4 2
house, Bristol
This spacious 4-bedroom property is situated in Bradley Stoke, Bristol, 2.6 kilometres from Bristol Parkway Station and within 12.7 kilometres of Bristol Temple Meads Station and Cabot Circus.
This detached house offers accommodation for up to 7 guests, featuring a well-equipped kitchen with a dishwasher, a private garden with seating, a balcony, free private parking, and is close to cycling routes.
Private 2bed-parking & Garden-by Fabaccommodation - Chepstow
9.3 14 reviews
Chepstow
19/08 – 26/08
NZ$472/nighttotal: NZ$3304 (7 )

Private 2bed-parking & Garden-by Fabaccommodation

2 4
apartment, Bristol
This recently renovated two-bedroom flat is located just 2.6 miles from Bristol Parkway Station and 6 miles from Bristol Zoo, offering easy access to the city's attractions. The property has received excellent ratings for its cleanliness, location, and overall experience, making it a great choice for a comfortable stay.
The 74 square metre flat comfortably accommodates up to four guests and features a well-equipped kitchen, a private garden, and free parking. Enjoy meals on the patio, relax in the garden, or take advantage of the on-site mini-market for convenience.

Best pet friendly Chepstow holiday rentals

Among the 28 accommodations in Chepstow, here are the 4 best pet friendly rentals

Oak - Uk50462 - Chepstow
Chepstow
27/06 – 04/07
NZ$277/nighttotal: NZ$1939 (7 )

Oak - Uk50462

1 2
apartment, Gloucestershire
This ground floor stable conversion in Aylburton, Gloucestershire, offers views over the Severn estuary and is situated a short drive from Lydney and the Forest of Dean, with attractions such as Puzzlewood, Symonds Yat, Tintern Abbey, and Clearwell Caves nearby. This property provides accommodation for two guests with one bedroom and one bathroom, featuring an open-plan living space, a fully equipped kitchen with a dishwasher, and an enclosed front garden with sitting-out area and barbecue.
The Old Rectory - Chepstow
9.7 3 reviews
Chepstow
27/06 – 04/07
NZ$2108/nighttotal: NZ$14756 (7 )

The Old Rectory

5 2
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.
Hopewell Barn - Chepstow
Chepstow
27/06 – 04/07
NZ$403/nighttotal: NZ$2821 (7 )

Hopewell Barn

3 2
house, Hewelsfield
Hopewell Barn, a detached house in Hewelsfield, is situated approximately 32 to 42 kilometres from Bristol Parkway Station and Bristol Cathedral, offering a countryside retreat.
This property accommodates up to 9 guests in 3 bedrooms and 2 bathrooms, featuring a dishwasher, fireplace, garden, and private parking with an electric vehicle charging point.
3 Bedroom Cottage - Cozy Wood Burner, Parking Wifi - Chepstow
9.7 31 reviews
Chepstow
19/08 – 26/08
NZ$421/nighttotal: NZ$2947 (7 )

3 Bedroom Cottage - Cozy Wood Burner, Parking Wifi

3 4
apartment, Pilning
Wave Cottage is located in Pilning Village, just a short drive from The Wave surfing lagoon, Bristol city centre, and the M4 motorway, making it ideal for exploring the surrounding areas. The cottage offers a convenient and comfortable base for your stay, with easy access to local amenities and attractions.
The cottage has three bedrooms and two bathrooms, comfortably accommodating up to six guests. The property has a modern, open-plan kitchen, a secure garden, off-road parking for four cars, and an EV charging point, perfect for families and groups.
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