Holiday lettings & accommodation in Chepstow - HomeToGo base64Hash Holiday lettings & accommodation in Chepstow - HomeToGo

Holiday lettings & accommodation in Chepstow

Find 140 available offers from 13 partners
Chepstow
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Guests
Chepstow
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Choose the perfect holiday letting

Price per night
Up to £100
£100 - £199
From £200
Accommodation types
House
Apartment
Bed and breakfast
Rating
4.5+
4+

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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Best holiday lettings with a pool

A swimming pool is a holiday home staple, and with 11% of the holiday rentals in Chepstow providing pool access, there are plenty of great options from which to choose. Get ready to take a dip and dive into the top offers for accommodation with private pools in Chepstow.

House  Chepstow
2 Apr - 9 Apr
-33%
£741
£494 per night
House ∙ 10 guests ∙ 5 bedrooms

House in Oldbury-On-Severn with Pool

Chepstow, Monmouthshire, United Kingdom
Pool
Details
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Villa  Chepstow
21 Dec - 28 Dec
-4%
£846
£808 per night
Villa ∙ 8 guests ∙ 4 bedrooms

Villa in Tockington with Natural Pool

5.0
Outstanding (2 ratings)
Chepstow, Monmouthshire, United Kingdom
Pool
Details
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Villa  Chepstow
14 Jun - 21 Jun
£162 per night
Villa ∙ 2 guests ∙ 1 bedroom

Pleasant Villa in Tockington with Hot Tub, Pool & Terrace

Chepstow, Monmouthshire, United Kingdom
Free cancellation
Pool
Details
Agoda
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Recommended pet-friendly holiday lettings

Bringing a canine companion along on your travels? Whether they're exploring the surroundings or finding a spot in which to snuggle up on the sofa, your pet will be welcome at one of the 18 dog-friendly holiday lettings in Chepstow.

House  Chepstow
16 Apr - 23 Apr
£264 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Chepstow with Barbecue & Garden

Chepstow, Monmouthshire, United Kingdom
Pet-friendly
Details
HomeToGo
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Cottage  Chepstow
15 Apr - 22 Apr
-51%
£208
£103 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Pleasant Cottage in Tidenham with Private Parking

Chepstow, Monmouthshire, United Kingdom
Pet-friendly
Details
HomeToGo
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Cottage  Chepstow
24 May - 31 May
£133 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage in Itton Common with Garden + Outstanding Views

Chepstow, Monmouthshire, United Kingdom
Pet-friendly
Details
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Best holiday homes with a patio or terrace

Want to admire Chepstow's vistas from the comfort of a holiday apartment, or enjoy private outside space while staying in a Chepstow holiday home? Take a look at our top lettings with balconies and patios in Chepstow and find the perfect accommodation for your stay.

Cottage  Chepstow
11 Jan - 18 Jan
-62%
£603
£227 per night
Cottage ∙ 10 guests ∙ 5 bedrooms

Beautiful Cottage in Pilning with Garden, Barbecue, Hot Tub + Picturesque Views

Chepstow, Monmouthshire, United Kingdom
Balcony/Patio
Details
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Apartment  Chepstow
21 Sept - 28 Sept
£149 per night
Apartment ∙ 4 guests ∙ 1 bedroom

Flat in Woodcroft with Garden & Terrace + Garden View

4.8
Outstanding (18 ratings)
Chepstow, Monmouthshire, United Kingdom
Balcony/Patio
Details
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House  Chepstow
21 Dec - 28 Dec
-17%
£1,121
£935 per night
House ∙ 14 guests ∙ 5 bedrooms

Holiday Home in Caldicot with Barbecue, Terrace & Garden

4.9
Outstanding (37 ratings)
Chepstow, Monmouthshire, United Kingdom
Balcony/Patio
Details
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Best holiday rental deals in Chepstow

Save up to 74%

Cottage Chepstow
19 Apr - 26 Apr
-74%
£441
£117 per night
Cottage ∙ 10 guests ∙ 5 bedrooms

Cottage in Tutshill with Garden

5.0
Outstanding (1 rating)
Chepstow, Monmouthshire, United Kingdom
Details
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Accommodation Chepstow
20 Apr - 27 Apr
-19%
£105
£86 per night
Accommodation ∙ 2 guests ∙ 1 bedroom

Wonderful Letting in Chepstow with Garden

4.4
Very good (35 ratings)
Chepstow, Monmouthshire, United Kingdom
Details
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Castle Chepstow
5 Apr - 12 Apr
-13%
£167
£146 per night
Castle ∙ 2 guests ∙ 1 bedroom

Castle in Mathern with Barbecue, Terrace & Garden

5.0
Outstanding (9 ratings)
Chepstow, Monmouthshire, United Kingdom
Details
Vrbo
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Find a holiday letting fitting your criteria among the 140 fantastic lettings from numerous partner websites in Chepstow. With HomeToGo you can instantly search and compare the offers for each property from various providers to find the best deal and save up to 18%.

Recommended holiday lettings in Chepstow

Rent a holiday home, apartment or cottage in Chepstow from just £55 per night

House Chepstow
19 Apr - 26 Apr
£264 per night
House ∙ 8 guests ∙ 1 bedroom

House in Chepstow with Garden

Chepstow, Monmouthshire, United Kingdom
Details
Expedia
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House Chepstow
15 Jul - 22 Jul
£517 per night
House ∙ 9 guests ∙ 3 bedrooms

Lovely Holiday Home in Mathern with Garden + Idyllic Views

Chepstow, Monmouthshire, United Kingdom
Details
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House Chepstow
6 Apr - 13 Apr
£575 per night
House ∙ 9 guests ∙ 3 bedrooms

Historic House in Chepstow with Garden

5.0
Outstanding (1 rating)
Chepstow, Monmouthshire, United Kingdom
Details
HolidayLettings
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Apartment Chepstow
4 Apr - 11 Apr
£149 per night
Apartment ∙ 8 guests ∙ 1 bedroom

Holiday Apartment in Woodcroft with Garden & Terrace

4.3
Very good (23 ratings)
Chepstow, Monmouthshire, United Kingdom
Details
Expedia
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House Chepstow
19 Aug - 26 Aug
£112 per night
House ∙ 2 guests ∙ 1 bedroom

House in Chepstow with Garden

4.9
Outstanding (19 ratings)
Chepstow, Monmouthshire, United Kingdom
Details
Vrbo
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Cottage Chepstow
20 Apr - 27 Apr
-18%
£169
£139 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Lovely Cottage in Mathern with Garden

Chepstow, Monmouthshire, United Kingdom
Details
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Castle Chepstow
15 Mar - 22 Mar
-13%
£804
£696 per night
Castle ∙ 16 guests ∙ 5 bedrooms

Nice Castle in Caldicot with Garden & Barbecue

Chepstow, Monmouthshire, United Kingdom
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Apartment Chepstow
4 Apr - 11 Apr
-20%
£95
£76 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Flat in Chepstow with Terrace & Garden

4.8
Outstanding
Chepstow, Monmouthshire, United Kingdom
Details
Agoda
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Apartment Chepstow
27 Apr - 4 May
£149 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Flat in Woodcroft with Terrace & Garden

4.4
Very good
Chepstow, Monmouthshire, United Kingdom
Free cancellation
Details
Agoda
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Budget-friendly Holiday Homes in Chepstow

Find Fantastic yet Cheap Lettings

Accommodation Chepstow
20 Apr - 27 Apr
-17%
£103
£86 per night
Accommodation ∙ 2 guests ∙ 1 bedroom

Letting in Chepstow with Garden

4.4
Very good (35 ratings)
Chepstow, Monmouthshire, United Kingdom
Details
HomeToGo
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Cottage Chepstow
4 May - 11 May
-18%
£194
£160 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage in Mathern with Garden

Chepstow, Monmouthshire, United Kingdom
Details
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House Chepstow
27 Apr - 4 May
£313 per night
House ∙ 6 guests ∙ 3 bedrooms

Holiday Home in Chepstow with Free Parking

Chepstow, Monmouthshire, United Kingdom
Free cancellation
Details
HolidayLettings
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Top-Rated Lettings and Properties in Chepstow

Book Holiday Letting Offers with the Highest User Rating

Cottage Chepstow
5 Oct - 12 Oct
-38%
£160
£100 per night
Cottage ∙ 2 guests ∙ 1 bedroom

Superior Cottage in Devauden with Garden, Terrace & Barbecue + Garden View

5.0
Outstanding (4 ratings)
Chepstow, Monmouthshire, United Kingdom
Details
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Cottage Chepstow
2 Nov - 9 Nov
-65%
£164
£58 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage in Llanvair-Discoed with Front Garden + Breath-Taking Views

5.0
Outstanding (1 rating)
Chepstow, Monmouthshire, United Kingdom
Details
HomeToGo
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Cottage Chepstow
15 Nov - 22 Nov
-62%
£158
£60 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage in Tintern with Barbecue, Hot Tub & Garden + Wonderful Views

4.9
Outstanding (30 ratings)
Chepstow, Monmouthshire, United Kingdom
Details
HomeToGo
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Popular holiday rental amenities in Chepstow

  • Pet-friendly (18)
  • Parking (2)
  • Pool (15)
  • Hot tub (12)
  • Fireplace (20)
  • WiFi (130)
  • Kitchen (54)
  • Fishing (30)
  • Balcony/patio (50)
  • Wheelchair access (22)
  • Garden (106)
  • No smoking (128)

Lettings can be selected based on various criteria. Just above, you will find the total number of lettings that provide a specific amenity in Chepstow. Our database shows that Internet and Garden are the most commonly offered amenities in Chepstow. Three features that aren't often available are Hot tub, Sauna and Barbecue.

The Weather in Chepstow

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11 days 11
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12 days 12
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12 days 12
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13 days 13
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11 days 11
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12 days 12
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16 days 16
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Above is a climate diagram for Chepstow. Usually, the warmest month is July. In contrast, the coolest month is February. April is the driest month of the year in Chepstow.

7-Day Weather Forecast in Chepstow

Thu, 28 Mar
10°

90%

0 h

31 km/h

Fri, 29 Mar
12°
10°

35%

2 h

25 km/h

Sat, 30 Mar
13°
11°

25%

2 h

9 km/h

Sun, 31 Mar
14°
12°

0%

1 h

20 km/h

Mon, 1 Apr
11°

50%

1 h

15 km/h

Tue, 2 Apr
12°
11°

0%

1 h

14 km/h

Wed, 3 Apr
12°
12°

0%

2 h

16 km/h

Accommodation options for your holiday in Chepstow

One-third of the listings (35.71%) in Chepstow are cottage. They are the most common holiday lettings there. Cottage here have an average price of £272 a night as well as a median size of 184 m². Furthermore, this type of residence tends to be an excellent option for medium-sized groups and families, as most of the cottage are able to welcome at least 6 people. A house rentals is the second most frequently offered type of rental in Chepstow. House rentals in Chepstow usually have an average size of 133 m².
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.

Information about holiday rentals in Chepstow

🏡 Holiday homes available 140 rentals
💳 Discounts available up to 18%
🌙 Nightly prices from £55
⭐ Popular amenities Pets allowed, Parking and Pool
🐾 Pet friendly rentals 18 properties
🏊 Holiday rentals with pools 15 properties

Frequently Asked Questions

How many holiday homes are available to book in Chepstow?

Currently there are 140 holiday homes from 13 providers on offer in Chepstow.

What is the most searched holiday apartment amenity in Chepstow?

Three most popular holiday rental amenities among our customers in Chepstow are Pets allowed, Parking and Pool.

How many holiday rentals in Chepstow have a pool?

Holiday rentals with pools are 11 of all offers in Chepstow with an average rate of £148 per night.

May i bring my pet while staying in a Chepstow holiday letting?

Dogs are welcome in Chepstow which is home to 18 pet-friendly holiday lettings.

What is the best time of year to travel to Chepstow?

April and May are the months with the least amount of rain in Chepstow.

How do I find deals on holiday accommmodation in Chepstow?

You can get brilliant bargains on holiday accommodation in Chepstow with prices for a let starting at just £55 - and HomeToGo has created a range of filters that make it easy to uncover the best deals. If you don't have set dates for your break, you can use HomeToGo's flexible dates technology to quickly locate great value date options and get discounts of up to 18%. Additionally, HomeToGo's 'distance from' filter can help you find hidden gem holiday homes in great value, lesser-known locales with good proximity to your desired destination, whether that's the coastline, a swimming lake, winter sports area or town centre. Start your search as soon as possible to get the best of the greatest variety of options and low prices - and do so without worries by using HomeToGo's 'free cancellation' filter when searching for holiday accommodation.

What are the benefits of finding a holiday rental in Chepstow with HomeToGo?

From serenity away from the crowds to plenty of room to enjoy with your loved ones, holiday lettings in Chepstow provide many advantages. HomeToGo surfaces real reviews from verified visitors, and searching is secure, easy, and hassle-free - so with 140 offers from 13 providers in the area, you're guaranteed to uncover the perfect place to stay with all of the amenities that are important to you in Chepstow.

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