Holiday lettings & accommodation in Chepstow

Compare 20 available properties from 11 providers
2 guests

Choose the perfect holiday letting

Price per night
Up to £100
£100 - £199
From £200
Accommodation types
Bed & Breakfast
Private room
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+

Recommended holiday lettings in Chepstow

Rent a holiday home, apartment or cottage in Chepstow from just £40 per night

Private room Chepstow 2
Private room ∙ 2 guests ∙ 1 bedroom
Chepstow, Monmouthshire, United Kingdom
from £42
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Best holiday lettings with a pool

House Pool Chepstow
House ∙ 10 guests ∙ 5 bedrooms
Chepstow, Monmouthshire, United Kingdom
from £522
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Recommended pet-friendly holiday lettings

Cottage Pet-friendly Chepstow
Cottage ∙ 6 guests ∙ 3 bedrooms
Chepstow, Monmouthshire, United Kingdom
from £66
Sykes Cottages
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House Pet-friendly Chepstow
House ∙ 16 guests ∙ 7 bedrooms
Chepstow, Monmouthshire, United Kingdom
from £520
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House Pet-friendly Chepstow
5 Dec - 12 Dec
House ∙ 21 guests ∙ 9 bedrooms
Chepstow, Monmouthshire, United Kingdom
from £636 £832
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Best holiday rentals with a balcony

House Balcony Chepstow
House ∙ 10 guests ∙ 5 bedrooms
Chepstow, Monmouthshire, United Kingdom
from £317
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Popular holiday rental amenities in Chepstow

  • Internet (14)
  • TV (12)
  • Parking (12)
  • Garden (11)
  • Balcony/Patio (8)
  • No smoking (8)
  • Washing machine (6)
  • No pets (6)
  • BBQ (5)
  • Kitchen (4)
  • Fishing (4)
  • Pet allowed (3)

Using our selection of filters can help you find your dream property in Chepstow. Our data highlights that internet and TVs turn out to be the most frequently offered features in Chepstow. You can also find a property if you want a rental providing a cot, as 1 of the listed rentals there include cots.

The Weather in Chepstow

- 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 January, while the driest month is March.

Accommodation options for your holiday in Chepstow

In Chepstow, hotel rooms are the most common type of accommodation on offer. The average cost of this specific accommodation type is £68 per night, with an average size of 17 m². Moreover, this specific type of lodging tends to be an excellent option for couples and small groups, since the majority of hotel rooms can host at least 3 people. You can also compare other accommodation options in Chepstow. For example, bed & breakfast rentals are another typical type of accommodation in Chepstow, with 9 offers listed. The average size of bed & breakfast rentals in Chepstow is 36 m², and the average price is £73 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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What are the best places to discover the arts and culture of Chepstow?

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.

What are the best activities for families in Chepstow?

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.

Where are the unique attractions in Chepstow?

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 2,000 providers, including: Holiday Rentals in Chepstow Novasol Holiday Rentals in Chepstow TripAdvisor Holiday Rentals in Chepstow Airbnb 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 Holiday Rentals in Chepstow HouseTrip Holiday Rentals in Chepstow Belvilla Holiday Rentals in Chepstow Sykes Cottages Holiday Rentals in Chepstow Holiday Rentals in Chepstow Ski Planet Holiday Rentals in Chepstow Only-apartments Holiday Rentals in Chepstow James Villa Holidays Holiday Rentals in Chepstow