Holiday Rentals in Chepstow

28 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • bookabach
  • expedia
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelscom
  • hotelopia
Chepstow holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

28 Holiday Rentals and Airbnb in Chepstow

Best family friendly Chepstow holiday rentals

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

Cottage ∙ 1 Bedroom ∙ 3 Guests - Chepstow
10 1 review
Chepstow
29/08 – 30/08
NZ$694/nightfor 1 night

Cottage ∙ 1 Bedroom ∙ 3 Guests

1 2
cottage , Llanvair-Discoed
The Snug, a single-storey cottage, is situated on the outskirts of Llanvair Discoed, Monmouthshire, 5km from Caerwent with its Roman ruins and farmer's market.
This 90 square metre self-catering studio offers a king-size bed and sofa bed sleeping up to three guests, boasting a private patio and easy access to attractions like Caldicot and Chepstow Castles.
Large Modern Home, Free Parking, Families And Contractors Welcome - Chepstow
9.0 9 reviews
Chepstow
21/06 – 23/06
NZ$493/nighttotal: NZ$986 (2 )

Large Modern Home, Free Parking, Families And Contractors Welcome

3 2
house , Bristol
This spacious Bristol house is situated 4.3km from Bristol Parkway Station and 11km from Clifton, offering easy access to both the station and the Clifton Suspension Bridge.
The 95 square metre property sleeps up to 11 guests in three bedrooms, two bathrooms, and boasts free Wi-Fi, parking, a garden, and a fully equipped kitchen including a microwave and dishwasher.
Bright & Modern| Free Parking & Nr Bristol Parkway - Chepstow
10 6 reviews
Chepstow
01/07 – 31/07
NZ$324/nighttotal: NZ$9720 (30 )

Bright & Modern| Free Parking & Nr Bristol Parkway

1 3
apartment , Bradley Stoke
This two-bedroom house in Bradley Stoke is less than 1.5km from Bristol Parkway station, providing easy access to Bristol city centre and the M4/M5 motorways.
The property, sleeping up to four guests, offers free parking, Wi-Fi, a garden, and a kitchen equipped with a fridge, freezer, and microwave; nearby amenities include a Tesco Express and a pub within 800 metres.
Chepstow Town. Welsh Cottage. - Chepstow
9.9 293 reviews
Chepstow
21/06 – 23/06
NZ$251/nighttotal: NZ$502 (2 )

Chepstow Town. Welsh Cottage.

1 2
house , Chepstow
This charming house is located in the centre of Chepstow, just a short walk from the castle, Priory Church, and the River Wye. It has received excellent ratings for its location, cleanliness, and overall user experience.
The house is ideal for families, with two bedrooms and a guest capacity of four. It offers a spacious living area, a fully equipped kitchen, and a private garden, perfect for enjoying the beautiful surroundings.

Best Chepstow holiday rentals with parking

Spacious 3-bedroom Home With Fast Wi-fi Near M4, M5 & M32 - Chepstow
Chepstow
29/08 – 30/08
NZ$620/nightfor 1 night

Spacious 3-bedroom Home With Fast Wi-fi Near M4, M5 & M32

3 2
apartment , Bradley Stoke
This Bradley Stoke flat is conveniently located for exploring Bristol and its surroundings, with Aztec West Activity Park just 6 minutes by car and the Kennet and Avon Canal and Wye Valley a 16-minute drive away.
This 3-bedroom, 2-bathroom property accommodates up to 5 guests and includes essential amenities such as Wi-Fi, heating, a dryer, ironing board, toiletries, and linens, offering easy access to attractions like Bristol Hippodrome (13 minutes by car), Bristol Zoo Project, and We The Curious science museum.
Spacious Home | Parking | Families & Contractors - Chepstow
9.3 6 reviews
Chepstow
01/07 – 31/07
NZ$373/nighttotal: NZ$11190 (30 )

Spacious Home | Parking | Families & Contractors

3 3
apartment , Bradley Stoke
This three-bedroom, two-bathroom house in Bradley Stoke offers convenient access to the M4/M5 motorways (under 8km) and Cribbs Causeway shopping centre (under 16km).
Sleeping five comfortably, the property includes Wi-Fi, driveway parking, a private garden, and is ideally suited for families or contractors seeking a self-catering base near Bristol.
New 3 Bedroom Flat Close To Station - Chepstow
10 9 reviews
Chepstow
13/08 – 16/08
NZ$710/nighttotal: NZ$2130 (3 )

New 3 Bedroom Flat Close To Station

3 4
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.
New 4 Bed House Sleeps Up To 8 People - Chepstow
9.0 3 reviews
Chepstow
21/06 – 23/06
NZ$490/nighttotal: NZ$980 (2 )

New 4 Bed House Sleeps Up To 8 People

4 2
apartment , Chepstow
This spacious maisonette in Chepstow offers excellent proximity to Chepstow Station, facilitating easy travel and placing guests conveniently close to local amenities.
Boasting a generous 60 square meters of living space, this family-friendly property features four bedrooms, three bathrooms, a fully equipped kitchen with a fridge and microwave, private garden access, and complimentary on-site parking and Wi-Fi, comfortably accommodating up to 15 guests.

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

Splendid House Great Location To Wave Surf & South West Water Park - Super Garden By Stae-homes - Chepstow
9.8 4 reviews
Chepstow
24/07 – 27/07
NZ$611/nighttotal: NZ$1833 (3 )

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

3 5
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.
Nj&c Properties - Chepstow
9.3 4 reviews
Chepstow
21/06 – 23/06
NZ$237/nighttotal: NZ$474 (2 )

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.
Betty Shepherd's Hut - Chepstow
10 12 reviews
Chepstow
21/06 – 23/06
NZ$456/nighttotal: NZ$912 (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.
Baker's Bun - Sleeps 7 - Spacious Home - Parking & Garden - Bradley Stoke Bristol - Chepstow
Chepstow
01/07 – 31/07
NZ$478/nighttotal: NZ$14340 (30 )

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

4 3
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.

Best pet friendly Chepstow holiday rentals

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

The Snug - Chepstow
9.0 8 reviews
Chepstow
21/06 – 23/06
NZ$372/nighttotal: NZ$744 (2 )

The Snug

1 2
house , Chepstow
The Snug is located in Chepstow, a charming town 32 kilometres from Bristol and 48 kilometres from Cardiff, offering easy access to both cities and their attractions. It's situated in a peaceful area, perfect for a relaxing getaway.
The cottage offers 90 square metres of space, with one bedroom and one bathroom, comfortably accommodating up to five guests. It features a fully equipped kitchen, a relaxing garden, and private parking, providing everything you need for a comfortable stay.
2 Bed Barn, Open Living Space , Pet Friendly, Rural, With Easy Access From M4 - Chepstow
10 3 reviews
Chepstow
24/07 – 27/07
NZ$470/nighttotal: NZ$1410 (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.
The Foxes Den Shepherds Hut, Pet Friendly In Oldbury-on-severn - Chepstow
10 1 review
Chepstow
29/08 – 30/08
NZ$755/nightfor 1 night

The Foxes Den Shepherds Hut, Pet Friendly In Oldbury-on-severn

1 2
cottage , Bristol
This pet-friendly cottage is located in Shepperdine, Bristol, just 8 kilometres from Thornbury Castle and 19 kilometres from Chepstow Racecourse, offering a peaceful retreat in the countryside. The cottage provides a comfortable base for exploring the surrounding area, with a 90 square metre floor area and a capacity for two guests.
The cottage comes with a fully equipped kitchen, a garden, a fireplace, and amenities such as linens and heating. Guests can enjoy activities like fishing, cycling, and exploring the beautiful countryside, or visit nearby attractions such as Thornbury Golf Centre, West Country Water Park, and Slimbridge Wildfowl and Wetlands Centre.
The Potting Shed At Mathern Palace - Chepstow
9.9 41 reviews
Chepstow
21/06 – 23/06
NZ$400/nighttotal: NZ$800 (2 )

The Potting Shed At Mathern Palace

2 2
house , Chepstow
The Potting Shed is a charming holiday home located just 22 kilometres from Bristol Parkway Station and 29 kilometres from Bristol Zoo, offering a tranquil retreat in the heart of Chepstow. The property has received excellent ratings for its location, cleanliness and overall experience.
The cottage has two bedrooms and one bathroom, comfortably accommodating up to four guests. Guests can enjoy a well-equipped kitchen with a dishwasher, a private garden, and free parking and Wi-Fi.
©2026 cozycozy.com