Holiday Rentals in Chepstow

28 available vacation rental offers

7 nights
2
1
  • tripcom
  • booking
  • airbnb
  • tripadvisor
  • klook
  • agoda
  • expedia
  • hotelscom
  • hotelscombined
  • eztravel
  • makemytrip
  • rakutentravel
Chepstow holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

Chepstow holiday rentals: compare the best deals

Best family friendly Chepstow holiday rentals

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

New 3 Bedroom Apartment Next To Station - Chepstow
8.8 7 reviews
Chepstow
08/08 – 08/10
HK$3350/nighttotal: HK$6700 (2 )

New 3 Bedroom Apartment Next To Station

3 7
apartment , Chepstow
This 3-bedroom flat in Moffat offers convenient access to golf clubs, with Dumfries and County Golf Club 38.6 kilometres away and Dumfries and Galloway Golf Club 40.2 kilometres distant.
This apartment provides free WiFi, a fully equipped kitchen, and parking, accommodating up to 11 guests with a peaceful setting ideal for relaxation.
Charming 4-bedroom Cottage In Historic Chepstow - Chepstow
10 3 reviews
Chepstow
08/19 – 08/26
HK$3436/nighttotal: HK$24052 (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.
Hawthorn View: Bristol Large House Stae-homes - Chepstow
Chepstow
08/19 – 08/26
HK$2011/nighttotal: HK$14077 (7 )

Hawthorn View: Bristol Large House Stae-homes

3 4
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.
The Elements Residence - Chepstow
Chepstow
07/01 – 07/02
HK$10239/nightfor 1 night

The Elements Residence

10 1
apartment , Chepstow
The Chepstow Hive, a large dwelling in Chepstow, is situated 21 kilometres from Bristol Parkway Station and 29 kilometres from Bristol Cathedral.
This family-friendly property offers 275 square metres of space with 10 bedrooms, 8 bathrooms, a garden, and on-site parking, accommodating up to 43 guests.

Best Chepstow holiday rentals with parking

4 Bed Luxury Stay,hot Tub,sleeps 9,private Parking - Chepstow
Chepstow
06/28 – 06/30
HK$3597/nighttotal: HK$7194 (2 )

4 Bed Luxury Stay,hot Tub,sleeps 9,private Parking

1 2
house , Chepstow
This detached house in Chepstow is located 20.9 kilometres from Bristol Parkway Station and 27.4 kilometres from Cabot Circus.
This non-smoking property offers a private hot tub, WiFi, parking, a fully equipped kitchen, and terrace access, accommodating up to 17 guests with 1 bedroom and 2 bathrooms.
Cooks House By Cliftonvalley Apartments - Chepstow
8.7 3 reviews
Chepstow
08/19 – 08/26
HK$2849/nighttotal: HK$19943 (7 )

Cooks House By Cliftonvalley Apartments

3 4
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.
1 Bedroom Accommodation In Lydney, Forest Of Dean - Chepstow
Chepstow
06/27 – 07/04
HK$1262/nighttotal: HK$8834 (7 )

1 Bedroom Accommodation In Lydney, Forest Of Dean

1 2
cottage , Lydney, Forest of dean
This ground floor stable conversion in Aylburton, near Lydney, Gloucestershire, offers Severn estuary views and 1.6 kilometers of access to the Forest of Dean, with Puzzlewood and Symonds Yat within easy reach.
This pet-friendly cottage accommodates two guests in one bedroom and features a king-size bed, Smart TV, fully equipped kitchen, enclosed garden with a barbecue, and private parking, ideal for romantic breaks and outdoor pursuits.
Anne's Hut Offers A Romantic Retreat For Two In Two Interlinked Shepherd's Huts With Decking Area An - Chepstow
10 4 reviews
Chepstow
06/27 – 07/04
HK$1894/nighttotal: HK$13258 (7 )

Anne's Hut Offers A Romantic Retreat For Two In Two Interlinked Shepherd's Huts With Decking Area An

1 2
cabin , Penterry, near Chepstow
Anne's Hut is a secluded shepherd's hut retreat located in a meadow on the edge of a wood near the ancient settlement of Penterry, just 5km from Chepstow and 10km from Tintern. The accommodation has received excellent ratings from previous guests for its cleanliness, location and overall experience.
The charming hut comprises two linked shepherd's huts, providing a comfortable space for two guests. The hut features a wood-burning stove, a well-equipped kitchen, a comfortable super-king size bed, a luxurious bathroom with a double-ended bath and rain shower, a decking patio area, and a fire pit and barbecue for outdoor cooking and relaxation.

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 right on the banks of the River Wye. The town itself has some charming historic buildings, like the 15th century St. Mary's Church. If you're looking for something a little different, the nearby Tintern Abbey is a beautiful ruined abbey with stunning views.
  • What are the best Airbnb and vacation rentals in Chepstow?

    Chepstow Town - Welsh Cottage, Sedbury Farm Cottages #2 and Peaceful - Rural Apartment With River Views are the most popular Airbnb and vacation rentals in Chepstow among travelers.

  • Which walking or cycling routes are the best in Chepstow?

    The Offa's Dyke Path is a classic long-distance trail that runs right through Chepstow. For a shorter walk, you can explore the Wye Valley Walk, which takes you along the river and through some lovely countryside. If you're into cycling, the Severn Estuary Trail is a great option, offering stunning views of the river.
  • 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 Racecourse is famous for its National Hunt racing. The River Wye is great for kayaking, canoeing, and paddleboarding. There's also some great mountain biking trails in the Forest of Dean, just a short drive away.
  • What are the best vacation rentals with a pool in Chepstow?

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

    You can easily reach Bristol by car or train, it's about a 45-minute drive. Monmouth, a charming market town, is just a short drive away, and you can also reach Newport in about 30 minutes by car.
  • What are the best rentals for families and kids in Chepstow?

    The best rentals for families and kids in Chepstow are Chepstow Town - Welsh Cottage, Sedbury Farm Cottages #2 and Sedbury Farm Cottages.

  • What amenities are commonly available in vacation rentals in Chepstow?

    Most vacation rentals in Chepstow will have basic amenities like Wi-Fi, a kitchen, and a bathroom. Many also offer things like a garden, parking, and a washing machine.
  • 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?

    The best time to visit Chepstow is during the spring or autumn, when the weather is mild and the crowds are smaller. You'll be able to enjoy the outdoors without the summer heat and humidity.
  • What are the local dishes in Chepstow region?

    The local area is known for its fresh seafood, especially salmon and trout from the River Wye. You'll also find plenty of traditional Welsh dishes like Welsh lamb and Cawl, a hearty vegetable stew. Don't forget to try the local cider!

Destinations nearby

Best Chepstow holiday rentals with a balcony

Gorgeous 3 Bed House In Bristol - Chepstow
8.1 14 reviews
Chepstow
06/27 – 07/04
HK$1819/nighttotal: HK$12733 (7 )

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.
Welsh Gatehouse: Historical Castle With Ev Charger - Chepstow
9.8 204 reviews
Chepstow
07/01 – 07/02
HK$2561/nightfor 1 night

Welsh Gatehouse: Historical Castle With Ev Charger

1 1
castle , Chepstow
This castle is located just 1.5 kilometres from St. Pierre Country Club, and within 5 kilometres of both the River Wye and Chepstow Castle, making it a great base for exploring the area. Guests have consistently rated this property excellent for its location, cleanliness, and overall experience.
This one-bedroom castle offers 55 square metres of space, comfortably accommodating up to 2 guests. Enjoy a peaceful retreat with a garden, barbecue facilities, and a terrace, perfect for soaking up the Welsh sunshine.
Baker's Bun - Sleeps 7 - Spacious Home - Parking & Garden - Bradley Stoke Bristol - Chepstow
Chepstow
06/27 – 07/04
HK$1819/nighttotal: HK$12733 (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.
Splendid House Great Location To Wave Surf & South West Water Park - Super Garden By Stae-homes - Chepstow
9.7 4 reviews
Chepstow
08/19 – 08/26
HK$2064/nighttotal: HK$14448 (7 )

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

3 4
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.

Best pet friendly Chepstow holiday rentals

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

Private 2bed-parking & Garden-by Fabaccommodation - Chepstow
9.3 14 reviews
Chepstow
08/19 – 08/26
HK$2151/nighttotal: HK$15057 (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.
Tawny Cottage - Chepstow
Chepstow
07/24 – 07/25
HK$8596/nightfor 1 night

Tawny Cottage

1 4
house , Usk
Tawny Cottage in Llandenny offers a peaceful base, located 38 kilometres from Bristol Parkway Station, 45 kilometres from Cabot Circus, and 46 kilometres from Cardiff's Motorpoint Arena and Cardiff University.
This 130 square metre holiday cottage accommodates up to 9 guests with 3 bedrooms and 2 bathrooms, featuring a fully equipped kitchen with a dishwasher, complimentary WiFi, private parking, and a garden, with golfing, cycling, and fishing available nearby.
Our Pet-friendly Accommodation Is Ideal For An Escape To The Countryside. - Chepstow
10 4 reviews
Chepstow
08/19 – 08/26
HK$825/nighttotal: HK$5775 (7 )

Our Pet-friendly Accommodation Is Ideal For An Escape To The Countryside.

1 4
apartment , Woolaston
This Lydney holiday home, located 5km from Taurus Crafts and within 10km of the River Wye and Symonds Yat Rock, offers a convenient base for exploring the Woolaston area.
The one-bedroom property sleeps four guests and boasts a fully equipped kitchen with dishwasher, a Smart TV, barbecue facilities, and free parking, perfect for a relaxing getaway near Lydney Harbour and Gate House.
Lushmint&sound - Chepstow
10 1 review
Chepstow
07/24 – 07/25
HK$2271/nightfor 1 night

Lushmint&sound

3 4
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.
©2026 cozycozy.com