Holiday rentals in Chepstow

Compare 130 available properties from 20 providers
Chepstow
Anytime
2 guests

Find a letting that fits your criteria among the 130 great holiday rentals from 20 holiday letting websites in Chepstow. Our search engine instantly evaluates the properties to help you save up to 10%.

Recommended holiday lettings in Chepstow

Rent a holiday home, apartment or cottage in Chepstow from just £23 per night

House ∙ 6 guests ∙ 3 bedrooms
Chepstow, Monmouthshire, United Kingdom
from £75
HomeAway
5.0
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House ∙ 2 guests ∙ 1 bedroom
Chepstow, Monmouthshire, United Kingdom
from £22
Airbnb
5.0
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Cottage ∙ 4 guests ∙ 2 bedrooms
Chepstow, Monmouthshire, United Kingdom
from £56
Airbnb
5.0
View deal
Cottage ∙ 2 guests ∙ 1 bedroom
Chepstow, Monmouthshire, United Kingdom
from £58
Airbnb
5.0
View deal
House ∙ 2 guests ∙ 1 bedroom
Chepstow, Monmouthshire, United Kingdom
from £40
Airbnb
5.0
View deal
House ∙ 2 guests ∙ 1 bedroom
Chepstow, Monmouthshire, United Kingdom
from £41
Airbnb
5.0
View deal
Apartment ∙ 4 guests ∙ 1 bedroom
Chepstow, Monmouthshire, United Kingdom
from £47
Airbnb
4.5
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House ∙ 2 guests ∙ 1 bedroom
Chepstow, Monmouthshire, United Kingdom
from £39
Airbnb
4.5
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House ∙ 2 guests ∙ 1 bedroom
Tutshill, Tidenham, United Kingdom
from £56
Airbnb
5.0
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Most popular holiday lettings with a fireplace

Fireplace
House ∙ 16 guests ∙ 8 bedrooms
Caldicot, Monmouthshire, United Kingdom
from £733
HomeAway
4.9
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Fireplace
House ∙ 3 guests ∙ 2 bedrooms
Chepstow, Monmouthshire, United Kingdom
from £36
Airbnb
4.5
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Fireplace
Cottage ∙ 4 guests ∙ 2 bedrooms
Chepstow, Monmouthshire, United Kingdom
from £70
Airbnb
5.0
View deal
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Recommended pet-friendly holiday lettings

Pet-friendly
Apartment ∙ 2 guests ∙ 1 bedroom
Chepstow, Monmouthshire, United Kingdom
from £64
Airbnb
5.0
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Pet-friendly
House ∙ 2 guests ∙ 1 bedroom
Chepstow, Monmouthshire, United Kingdom
from £40
Airbnb
5.0
View deal
Pet-friendly
Bed & Breakfast ∙ 2 guests
Chepstow, Monmouthshire, United Kingdom
from £70
Booking.com
4.3
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Best holiday homes with a patio or terrace

Balcony/Patio
House ∙ 2 guests
Chepstow, Monmouthshire, United Kingdom
from £70
Booking.com
4.0
View deal
Balcony/Patio
House ∙ 6 guests ∙ 3 bedrooms
Chepstow, Monmouthshire, United Kingdom
from £82
Booking.com
4.2
View deal
Balcony/Patio
Private room ∙ 6 guests
Caerwent, Monmouthshire, United Kingdom
from £95
Booking.com
4.8
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Popular holiday rental amenities in Chepstow

  • Internet (105)
  • TV (99)
  • Kitchen (95)
  • No smoking (68)
  • Garden (65)
  • Washer (50)
  • Parking (45)
  • Microwave (42)
  • Pet allowed (39)
  • Balcony/Patio (32)
  • Fireplace (32)
  • BBQ (30)

The Weather in Chepstow



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- Rainy days

Check out the climate diagram for Chepstow. This year, July will have the highest average temperatures. On the other hand, you could have temperatures dropping under 3° in February. The rainiest month is July, while the driest month is March.

Accommodation options in Chepstow

In Chepstow, house rentals are the most common type of accommodation on offer. The average cost of this specific accommodation type is £144 per night, with an average size of 107 m². Moreover, this specific type of lodging tends to be an excellent option for medium-sized groups and families, since the majority of house rentals can host at least 4 people. You can also compare other accommodation options in Chepstow. For example, hotel rooms are another typical type of accommodation in Chepstow, with 31 offers listed. The average size of hotel rooms in Chepstow is 23 m², and the average price is £83 a night.

Discover Iron Age hill forts with a Chepstow holiday cottage

The Normans considered the area around Chepstow worth claiming over a thousand years ago. Besides an impressive castle on the River Wye and the lush Wye Valley, there's plenty to see and do with family or friends at Chepstow accommodations.

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Art & Culture

Ancient history

Rediscover this ancient port town at the confluence of the wine trade, shipbuilding, and salmon fishing. Chepstow Museum presents photographs, posters, and prints illustrating the heritage of Chepstow through the ages, along with riveting artefacts from its long history.

A thousand years old, Chepstow Castle is the proud owner of one of the oldest castle doors in Europe. The castle has morphed through the ages to reflect architectural trends and military technology. For centuries, the castle was used as a stronghold, and its colourful history is contained in its onsite museum.

Family Activities

Grottoes and painting

Just a few minutes from Tintern Abbey, Ladybird Pottery offers your family the opportunity to get crafty. Choose from an array of pottery and create artwork you can take home as a souvenir of your holiday.

Children love to explore Dewstow Gardens & Grottoes, which were developed during the golden age of gardening, in the late 1800s. Wend your way through meandering paths to water features and intriguing focal points, past exotic plants and lush vegetation.

Local Attractions

Roman remains

Caerwent Roman Town is a haven for aspiring archaeologists. Once the capital of the Silures tribe, it has 4th-century walls, a forum, and temple.

Meanwhile, Offa's Dyke Path, a National Trail, winds through the breathtaking and brilliant green Brecon Beacons National Park, connecting with the Shropshire Hills and the Wye Valley. You'll pass Iron Age hillforts, castles, and impressive bridges as you explore this Area of Outstanding Natural Beauty. Don't miss the Devil's Pulpit, a limestone pillar overlooking Tintern Abbey, the subject of the famous Wordsworth poem.

We compare more than 600 providers, including:

Booking.com Holiday Rentals in Chepstow Novasol Holiday Rentals in Chepstow TripAdvisor Holiday Rentals in Chepstow Inter Chalet Holiday Rentals in Chepstow HomeAway Holiday Rentals in Chepstow EveryStay Holiday Rentals in Chepstow Interhome Holiday Rentals in Chepstow 9flats.com Holiday Rentals in Chepstow HouseTrip Holiday Rentals in Chepstow Belvilla Holiday Rentals in Chepstow Sykes Cottages Holiday Rentals in Chepstow Homestay.com Holiday Rentals in Chepstow Ski Planet Holiday Rentals in Chepstow Only-apartments Holiday Rentals in Chepstow James Villa Holidays Holiday Rentals in Chepstow