Holiday Rentals in Chepstow

28 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
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

Modern 2-bedroom Apartment - Chepstow
8.5 161 reviews
Chepstow
24/07 – 25/07
225 €/nightfor 1 night

Modern 2-bedroom Apartment

2 4
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.
Hawthorn View: Bristol Large House Stae-homes - Chepstow
Chepstow
19/08 – 26/08
222 €/nighttotal: 1554 € (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.
New 4 Bed House Sleeps Up To 8 People - Chepstow
9.0 3 reviews
Chepstow
28/06 – 30/06
247 €/nighttotal: 494 € (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.
Welsh Marches At Upper Glyn Farm - Chepstow
9.7 259 reviews
Chepstow
01/07 – 31/07
174 €/nighttotal: 5220 € (30 )

Welsh Marches At Upper Glyn Farm

1 3
house , Chepstow
This charming house is located just 17 miles from Bristol Parkway Station and 21 miles from Cabot Circus, making it a convenient base for exploring Chepstow and the surrounding area. The property has received excellent ratings for its cleanliness, location, and overall user experience.
The house features a well-equipped kitchen, a comfortable living area, and a private bathroom. Guests can enjoy a peaceful garden, a private terrace, and access to local activities like diving, cycling, and fishing.

Best Chepstow holiday rentals with parking

Sedbury Farm Cottages - Chepstow
8.3 143 reviews
Chepstow
08/08 – 10/08
313 €/nighttotal: 626 € (2 )

Sedbury Farm Cottages

4 7
apartment , Chepstow
Sedbury Farm Cottages offers a self-catering apartment in Chepstow, approximately 24 kilometres from Bristol Parkway Station and 31 kilometres from Cabot Circus in Bristol, close to Chepstow town centre and its historic attractions.
This family-friendly property features a private patio, free Wi-Fi, free parking, a fully equipped kitchen with dishwasher, a comfortable seating area with flat-screen TV, and a private bathroom; a relaxing garden is also available for guest use.
Fifty-five - Chepstow
8.5 83 reviews
Chepstow
24/07 – 25/07
197 €/nightfor 1 night

Fifty-five

3 4
apartment , Bristol
This Bristol apartment is conveniently located just 2.8 miles from Bristol Parkway Station and 6.2 miles from Bristol Zoo, offering a peaceful setting slightly outside the city centre. It has consistently received very good ratings for user experience, location, and cleanliness.
This three-bedroom property comfortably accommodates up to four guests and features a fully equipped kitchen with a fridge, microwave oven, and dishwasher. Enjoy a private garden, free parking, and a picnic area, perfect for relaxing after exploring Bristol.
The Honey Pot - Chepstow
9.9 34 reviews
Chepstow
01/07 – 02/07
562 €/nightfor 1 night

The Honey Pot

1 1
house , Chepstow
The Honey Pot is a charming holiday home located in Chepstow, just 21 miles from Bristol Zoo and 22 miles from Bristol Temple Meads Station, making it a great base for exploring both the town and the surrounding countryside. Guests have consistently rated the property highly for its cleanliness, location, and overall experience.
The house has one bedroom and one bathroom, offering comfortable accommodation for up to two guests. It boasts a fully equipped kitchen, a private garden with a hot tub, and free Wi-Fi, ensuring a relaxing and enjoyable stay.
Modern 2 Bed Home|bristol |Free Parking|nr Parkway - Chepstow
9.8 101 reviews
Chepstow
01/07 – 31/07
166 €/nighttotal: 4980 € (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.

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 one of the oldest and most impressive Norman castles in Wales. You'll also want to visit the historic town centre, with its beautiful old buildings and quaint shops. For a bit of nature, head over to the Wye Valley, just a short drive away. It's a stunning area of natural beauty with lots of walking trails.
  • 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 is a brilliant walk, following the ancient border between England and Wales. It's a bit of a trek, but you'll be rewarded with amazing views. For a shorter cycle, try the route along the River Wye. The scenery is beautiful, and it's relatively flat, so it's good for all levels.
  • 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, or try your hand at rock climbing at the nearby The Brecon Beacons National Park. There's also plenty of great walking and cycling in the area, and if you're feeling adventurous, you can even go paragliding. For something a bit more relaxed, there's the Chepstow Golf Club.
  • What are the best holiday rentals with a pool in Chepstow?

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

    You're well-placed to explore the rest of South Wales. Bristol is a vibrant city just an hour away by car, and you can easily reach Cardiff, the capital of Wales, in about an hour and a half. For a more scenic trip, head to the historic town of Monmouth, 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 Wi-Fi, a washing machine, and a TV. Many also have a garden or patio, and some even have a hot tub. Look out for rentals that are pet-friendly if you're bringing your furry friend along.
  • 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?

    It really depends what you're looking for! Summer is the busiest time, but you'll have the best weather for outdoor activities. Spring and autumn are lovely for walking and cycling, and you'll find fewer crowds. Winter can be chilly, but it's a great time to explore the local pubs and restaurants.

Destinations nearby

Best Chepstow holiday rentals with a balcony

Large Modern Home, Free Parking, Families And Contractors Welcome - Chepstow
9.0 9 reviews
Chepstow
19/08 – 26/08
236 €/nighttotal: 1652 € (7 )

Large Modern Home, Free Parking, Families And Contractors Welcome

3 4
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.
Welsh Gatehouse: Historical Castle With Ev Charger - Chepstow
9.8 204 reviews
Chepstow
01/07 – 02/07
283 €/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.
4 Bed Luxury Home, Sauna, Hot Tub, Sleeps 9 - Chepstow
10 1 review
Chepstow
08/08 – 10/08
744 €/nighttotal: 1488 € (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.
Splendid House Great Location To Wave Surf & South West Water Park - Super Garden By Stae-homes - Chepstow
9.7 4 reviews
Chepstow
19/08 – 26/08
228 €/nighttotal: 1596 € (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

Cottage ∙ 1 Bedroom ∙ 2 Guests - Chepstow
Chepstow
27/06 – 04/07
139 €/nighttotal: 973 € (7 )

Cottage ∙ 1 Bedroom ∙ 2 Guests

1 2
cottage , Aylburton
This ground floor stable conversion in Aylburton, Gloucestershire, offers views of the Severn estuary and is situated approximately 1.5 kilometers from Lydney town, providing easy access to the Forest of Dean's walking and cycling routes, as well as attractions such as Puzzlewood and Symonds Yat.
This pet-friendly, family-friendly cottage accommodates two guests in one bedroom and features an open-plan living space, a fully equipped kitchen, a shower room, an enclosed garden with seating and a barbecue, and private parking.
Edge Barn - Chepstow
9.6 180 reviews
Chepstow
19/08 – 26/08
198 €/nighttotal: 1386 € (7 )

Edge Barn

2 4
house , Woolaston
Edge Barn is situated in Woolaston, a tranquil village just 29 kilometres from Bristol Parkway Station and 37 kilometres from Bristol Temple Meads Station. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The property features two bedrooms and one bathroom, spanning 110 square metres and accommodating up to six guests. Edge Barn boasts a fully equipped kitchen, a private garden with river views, free Wi-Fi, and private parking, providing everything you need for a comfortable stay.
3 Bed In Trelleck Oc-j34206 - Chepstow
Chepstow
19/08 – 26/08
259 €/nighttotal: 1813 € (7 )

3 Bed In Trelleck Oc-j34206

3 4
house , Trelleck
This 3-bedroom detached house in Trelleck is located approximately 35-45 kilometres from Bristol Parkway Station, Bristol Temple Meads Station, and Bristol Cathedral.
This property offers accommodation for up to 10 guests with 2 bathrooms, a fully equipped kitchen including a microwave and dishwasher, free WiFi, private parking, and a garden.
The Nook - Farm Stay With Hot Tub - Chepstow - Chepstow
10 6 reviews
Chepstow
27/06 – 04/07
208 €/nighttotal: 1456 € (7 )

The Nook - Farm Stay With Hot Tub - Chepstow

1 2
cabin , Chepstow
This Chepstow countryside lodge is situated a short drive (approximately 5km) from the River Wye and Symonds Yat Rock, offering easy access to scenic walks and breathtaking views.
The 28 square metre self-catering retreat sleeps two, boasting a fully equipped kitchen, private garden, hot tub, and free Wi-Fi.
©2026 cozycozy.com