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

Holiday lettings & accommodation in Chepstow

Find 141 available offers from 8 partners
Chepstow
Anytime
Guests
Chepstow
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Guests

Popular Filters to discover the perfect holiday home in Chepstow

House
2 Adults
Pets allowed
Hot tub
Pool
Cottage
Cabin

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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Holiday rentals with wifi

Whether it's for working remotely or streaming your favourite shows, internet access can be an indispensable amenity when it comes to choosing a holiday home. Check out HomeToGo's range of holiday lettings with WiFi in Chepstow and enjoy a fast and reliable internet connection during your stay.

Cottage  Chepstow
2 Nov - 9 Nov
-73%
£466
£127 per night
Cottage ∙ 10 guests ∙ 5 bedrooms

Cottage in Tutshill with Garden

5.0
Outstanding (1 rating)
Chepstow, Monmouthshire, United Kingdom
Internet
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Cottage  Chepstow
18 Oct - 25 Oct
-58%
£261
£110 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Pleasant Cottage in Tidenham with Private Parking

Chepstow, Monmouthshire, United Kingdom
Internet
Details
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Cottage  Chepstow
9 Nov - 16 Nov
-72%
£869
£240 per night
Cottage ∙ 10 guests ∙ 5 bedrooms

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

Chepstow, Monmouthshire, United Kingdom
Internet
Details
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Best holiday rentals with a balcony

Want to see even more of Chepstow on your trip? Enjoy incredible views across this destination from your holiday home or apartment by booking a rental with a balcony in Chepstow.

House  Chepstow
1 Nov - 8 Nov
-46%
£242
£131 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Tintern with Front Garden + Panoramic Views

5.0
Outstanding (101 ratings)
Chepstow, Monmouthshire, United Kingdom
Balcony
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House  Chepstow
24 Aug - 31 Aug
£92 per night
House ∙ 4 guests ∙ 2 bedrooms

House in Devauden with Terrace & Garden

4.9
Outstanding (64 ratings)
Chepstow, Monmouthshire, United Kingdom
Free cancellation
Balcony
Details
HolidayLettings
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House  Chepstow
28 Jun - 5 Jul
£212 per night
House ∙ 4 guests ∙ 1 bedroom

Lovely Holiday Home in Woolaston with Terrace & Garden

5.0
Outstanding (5 ratings)
Chepstow, Monmouthshire, United Kingdom
Free cancellation
Balcony
Details
HolidayLettings
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Most popular holiday lettings with a fireplace

Accommodation with a fireplace - what could make a stay in Chepstow cosier? Find a holiday rental for your snug escape today, and start looking forward to evenings in Chepstow spent wrapped up in front of a toasty, crackling fire.

House  Chepstow
1 Oct - 8 Oct
£277 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Chepstow with Barbecue & Garden

Chepstow, Monmouthshire, United Kingdom
Free cancellation
Fireplace
Details
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Apartment  Chepstow
1 Nov - 8 Nov
£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
Fireplace
Details
HomeToGo
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Castle  Chepstow
17 Aug - 24 Aug
-13%
£186
£162 per night
Castle ∙ 2 guests ∙ 1 bedroom

Castle in Mathern with Barbecue, Terrace & Garden

5.0
Outstanding (9 ratings)
Chepstow, Monmouthshire, United Kingdom
Fireplace
Details
Vrbo
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Best holiday rental deals in Chepstow

Save up to 18%

Cottage Chepstow
8 Jun - 15 Jun
-18%
£201
£165 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Lovely Cottage in Mathern with Garden

Chepstow, Monmouthshire, United Kingdom
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Castle Chepstow
10 Jan - 17 Jan
-13%
£876
£759 per night
Castle ∙ 16 guests ∙ 5 bedrooms

Nice Castle in Caldicot with Garden & Barbecue

5.0
Outstanding (1 rating)
Chepstow, Monmouthshire, United Kingdom
Details
Vrbo
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Cottage Chepstow
8 Jun - 15 Jun
-18%
£218
£179 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage in Mathern with Garden

Chepstow, Monmouthshire, United Kingdom
Details
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Find a holiday letting fitting your criteria among the 141 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 69%.

Recommended holiday lettings in Chepstow

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

House Chepstow
24 Jul - 31 Jul
£360 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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House Chepstow
8 Jun - 15 Jun
£222 per night
House ∙ 4 guests ∙ 2 bedrooms

Holiday Home in Mathern

Chepstow, Monmouthshire, United Kingdom
Free cancellation
Details
Agoda
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House Chepstow
10 Jan - 17 Jan
-15%
£920
£779 per night
House ∙ 14 guests ∙ 5 bedrooms

Holiday Home in Caldicot with Barbecue, Terrace & Garden

4.9
Outstanding (37 ratings)
Chepstow, Monmouthshire, United Kingdom
Details
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Apartment Chepstow
27 May - 3 Jun
£82 per night
Apartment ∙ 6 guests ∙ 1 bedroom

Flat in Chepstow with Terrace & Garden

4.8
Outstanding
Chepstow, Monmouthshire, United Kingdom
Details
Agoda
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Apartment Chepstow
1 Nov - 8 Nov
£134 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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House Chepstow
10 Jan - 17 Jan
£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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Accommodation Chepstow
10 Jan - 17 Jan
£185 per night
Accommodation ∙ 2 guests ∙ 1 bedroom

Letting in Mathern with Garden

4.9
Outstanding (87 ratings)
Chepstow, Monmouthshire, United Kingdom
Details
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Apartment Chepstow
1 Nov - 8 Nov
£149 per night
Apartment ∙ 8 guests ∙ 1 bedroom

Holiday Apartment in Woodcroft with Garden, Barbecue & Terrace

4.8
Outstanding (24 ratings)
Chepstow, Monmouthshire, United Kingdom
Details
Expedia
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Cottage Chepstow
24 Aug - 31 Aug
£135 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage in Itton Common with Garden + Outstanding Views

Chepstow, Monmouthshire, United Kingdom
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Budget-friendly Holiday Homes in Chepstow

Find Fantastic yet Cheap Lettings

House Chepstow
21 Jun - 28 Jun
£512 per night
House ∙ 9 guests ∙ 3 bedrooms

Lovely Holiday Home in Mathern with Garden + Idyllic Views

Chepstow, Monmouthshire, United Kingdom
Details
Vrbo
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Cottage Chepstow
16 Nov - 23 Nov
-71%
£359
£103 per night
Cottage ∙ 8 guests ∙ 3 bedrooms

Cottage in Saint Arvans with Large Patio + Spectacular Views

Chepstow, Monmouthshire, United Kingdom
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House Chepstow
8 Jun - 15 Jun
£206 per night
House ∙ 4 guests ∙ 2 bedrooms

Holiday Home in Mathern

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

Book Holiday Letting Offers with the Highest User Rating

Cottage Chepstow
27 Sept - 4 Oct
-35%
£143
£93 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
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Cottage Chepstow
1 Nov - 8 Nov
-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
9 Nov - 16 Nov
-70%
£244
£74 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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Popular holiday rental amenities in Chepstow

  • Pet-friendly (16)
  • Parking (2)
  • Pool (16)
  • Hot tub (13)
  • Fireplace (19)
  • WiFi (131)
  • Kitchen (55)
  • Fishing (29)
  • Balcony/patio (53)
  • Wheelchair access (23)
  • Garden (106)
  • No smoking (129)

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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15 days 15
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10 days 10
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11 days 11
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12 days 12
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21°
14°
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

Wed, 22 May
15°
15°

90%

0 h

16 km/h

Thu, 23 May
14°
14°

5%

0 h

20 km/h

Fri, 24 May
16°
16°

0%

3 h

18 km/h

Sat, 25 May
19°
18°

0%

2 h

12 km/h

Sun, 26 May
19°
18°

10%

2 h

10 km/h

Mon, 27 May
19°
17°

0%

4 h

12 km/h

Tue, 28 May
19°
18°

0%

3 h

12 km/h

Accommodation options for your holiday in Chepstow

One-third of the listings (33.33%) in Chepstow are cottage. They are the most common holiday lettings there. Cottage here have an average price of £290 a night as well as a median size of 190 m². Furthermore, this type of residence tends to be an excellent option for large groups, as most of the cottage are able to welcome at least 7 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 141 rentals
💳 Discounts available up to 69%
🌙 Nightly prices from £55
⭐ Popular amenities Pets allowed, Parking and Pool
🐾 Pet friendly rentals 16 properties
🏊 Holiday rentals with pools 16 properties

Frequently Asked Questions

How many holiday homes are available to book in Chepstow?

Currently there are 141 holiday homes from 8 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 £135 per night.

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

Dogs are welcome in Chepstow which is home to 16 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 69%. 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 141 offers from 8 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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