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

Holiday lettings and accommodation in Chepstow

Find 150 available offers from 8 partners
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Guests
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Top 15 Recommended holiday lettings in Chepstow

Find your perfect holiday home, apartment or cottage in Chepstow from just £50 per night!

House Chepstow
House ∙ 8 guests ∙ 4 bedrooms

Beautiful holiday home with 4 rooms for 8 persons

Chepstow, Monmouthshire, United Kingdom
from £120
per night
from £120
per night
View deal
Private room Chepstow
Private room ∙ 2 guests ∙ 1 bedroom

Private room with terrace, barbeque & garden

Chepstow, Monmouthshire, United Kingdom
from £55
per night
from £55
per night
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Accommodation Chepstow
Accommodation ∙ 2 guests ∙ 1 bedroom

Wonderful letting with garden

Chepstow, Monmouthshire, United Kingdom
from £81
per night
Excellent(41 ratings)
from £81
per night
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Apartment Chepstow
Apartment ∙ 5 guests ∙ 2 bedrooms

Pleasant flat with garden

Chepstow, Monmouthshire, United Kingdom
from £131
per night
from £131
per night
View deal
House Chepstow
House ∙ 10 guests ∙ 3 bedrooms

Holiday home with 3 rooms for 10 persons

Chepstow, Monmouthshire, United Kingdom
from £387
per night
from £387
per night
View deal
Bed and breakfast Chepstow
Bed and breakfast ∙ 4 guests ∙ 1 bedroom

B&B for 4 persons

Chepstow, Monmouthshire, United Kingdom
from £72
per night
Very good
from £72
per night
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Castle Chepstow
Castle ∙ 16 guests ∙ 5 bedrooms

Family-oriented nice castle with garden, jacuzzi & BBQ | Pets allowed

Chepstow, Monmouthshire, United Kingdom
from £752
per night
Outstanding(2 ratings)
from £752
per night
View deal
House Chepstow
House ∙ 2 guests ∙ 1 bedroom

House with garden | Nature view

Chepstow, Monmouthshire, United Kingdom
from £80
per night
Outstanding(31 ratings)
from £80
per night
View deal
House Chepstow
House ∙ 2 guests ∙ 1 bedroom

Charming holiday home with 1 room for 2 persons

Chepstow, Monmouthshire, United Kingdom
from £148
per night
from £148
per night
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House Chepstow
House ∙ 4 guests ∙ 2 bedrooms

Holiday home with 2 rooms for 4 persons

Chepstow, Monmouthshire, United Kingdom
from £221
per night
from £221
per night
View deal
Cottage Chepstow
Cottage ∙ 10 guests ∙ 1 bedroom

Cottage with garden

Chepstow, Monmouthshire, United Kingdom
from £111
per night
from £111
per night
View deal
House Chepstow
House ∙ 4 guests ∙ 2 bedrooms

Holiday home with 2 rooms for 4 persons

Chepstow, Monmouthshire, United Kingdom
from £208
per night
from £208
per night
View deal
House Chepstow
House ∙ 20 guests ∙ 5 bedrooms

Holiday home with hot tub, barbecue & terrace | Nature view | Suitable for remote work

Chepstow, Monmouthshire, United Kingdom
from £805
per night
Outstanding(39 ratings)
from £805
per night
View deal
Cottage Chepstow
Cottage ∙ 10 guests ∙ 3 bedrooms

Cottage with jacuzzi & garden

Chepstow, Monmouthshire, United Kingdom
from £189
per night
from £189
per night
View deal
Castle Chepstow
Castle ∙ 2 guests ∙ 1 bedroom

Castle with barbecue, terrace & garden | Good for workation

Chepstow, Monmouthshire, United Kingdom
from £127
per night
Outstanding(10 ratings)
from £127
per night
View deal

Most popular holiday lettings with a fireplace

Cottage  Chepstow
from £78 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage | River view

Chepstow, Monmouthshire, United Kingdom
Fireplace
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Cottage  Chepstow
from £97 per night
Cottage ∙ 4 guests ∙ 1 bedroom

Cottage with garden | River view

Chepstow, Monmouthshire, United Kingdom
Fireplace
View deal
Cottage  Chepstow
from £236 per night
Cottage ∙ 6 guests ∙ 3 bedrooms

Family-friendly pleasant cottage with garden & barbecue | Pets allowed

5.0
Outstanding(18 ratings)
Chepstow, Monmouthshire, United Kingdom
Fireplace
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Recommended pet-friendly holiday lettings

House  Chepstow
from £199 per night
House ∙ 6 guests ∙ 3 bedrooms

Wonderful house | Pet-friendly

Chepstow, Monmouthshire, United Kingdom
Pet-friendly
View deal
Cottage  Chepstow
from £120 per night
Cottage ∙ 8 guests ∙ 4 bedrooms

Cottage with garden

Chepstow, Monmouthshire, United Kingdom
Pet-friendly
View deal
Cottage  Chepstow
from £163 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage with garden

4.4
Very good(3 ratings)
Chepstow, Monmouthshire, United Kingdom
Pet-friendly
View deal
See all offers

Holiday homes and cottages with a garden

Cottage  Chepstow
from £106 per night
Cottage ∙ 10 guests ∙ 5 bedrooms

Cottage with garden

4.8
Outstanding(13 ratings)
Chepstow, Monmouthshire, United Kingdom
Garden
View deal
Accommodation  Chepstow
from £91 per night
Accommodation ∙ 2 guests ∙ 1 bedroom

Letting with garden

4.5
Excellent(41 ratings)
Chepstow, Monmouthshire, United Kingdom
Garden
View deal
House  Chepstow
from £117 per night
House ∙ 2 guests ∙ 1 bedroom

Holiday home with garden

Chepstow, Monmouthshire, United Kingdom
Garden
View deal
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Budget-friendly Holiday Homes in Chepstow

Find Fantastic yet Cheap Lettings

Apartment Chepstow
from £150 per night
Apartment ∙ 4 guests ∙ 1 bedroom

Flat with garden & terrace | Garden view

4.8
Outstanding(19 ratings)
Chepstow, Monmouthshire, United Kingdom
View deal
House Chepstow
from £127 per night
House ∙ 10 guests ∙ 5 bedrooms

House with 5 rooms for 10 persons

Chepstow, Monmouthshire, United Kingdom
View deal
Cottage Chepstow
from £347 per night
Cottage ∙ 10 guests ∙ 1 bedroom

Cottage with jacuzzi & garden

Chepstow, Monmouthshire, United Kingdom
View deal

Top-Rated Lettings and Properties in Chepstow

Book Holiday Letting Offers with the Highest User Rating

Cottage Chepstow
from £46 per night
Cottage ∙ 3 guests ∙ 1 bedroom

Children-friendly cottage with garden | Dogs allowed

5.0
Outstanding(1 rating)
Chepstow, Monmouthshire, United Kingdom
View deal
Cottage Chepstow
from £174 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Child-friendly cottage with jacuzzi, garden & barbecue

5.0
Outstanding(36 ratings)
Chepstow, Monmouthshire, United Kingdom
View deal
Cottage Chepstow
from £78 per night
Cottage ∙ 2 guests ∙ 1 bedroom

Cottage with hot tub & garden

5.0
Outstanding(28 ratings)
Chepstow, Monmouthshire, United Kingdom
View deal

Why choose HomeToGo?

Securely pay and stay your way

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Award-winning customer service

Award-winning customer service

Experience seamless, hands-on support for any booking questions or concerns.

Verified reviews

Verified reviews

Trust in the quality and comfort of your stay with verified guest reviews.

Price clarity, no surprises

Price clarity, no surprises

Spend your budget exactly as planned by comparing thousands of providers.

Smart search made simple

Smart search made simple

Transform holiday planning into a joy with advanced, AI-powered search tools.

Find your dream stay

Find your dream stay

Explore 15 million+ rentals, the world’s biggest selection of holiday homes.

Popular holiday rental amenities in Chepstow

  • Pet-friendly (41)
  • Pool (21)
  • Hot tub (18)
  • Fireplace (14)
  • WiFi (140)
  • Kitchen (64)
  • Fishing (29)
  • Balcony/patio (49)
  • Wheelchair access (29)
  • Garden (113)
  • No smoking (138)
  • Sauna (11)

If you own a pet, you should be able to easily find a pet-friendly holiday rental in Chepstow. Most pet-friendly properties in Chepstow are hotel room. Their average price is £182 per night. You can also find suitable city properties, as a few of the pet-friendly properties are centrally located (less than 2 kilometres from the city centre).

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.

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.

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.

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 150 rentals
🌙 Nightly prices from £50
⭐ Popular amenities Pets allowed, Pool and Hot tub
🐾 Pet friendly rentals 41 properties
🏊 Holiday rentals with pools 21 properties

Frequently Asked Questions

What is a common price per night for a holiday home in Chepstow?

The average price per night in Chepstow is around £50. The nightly rate for house rentals is £350 on average. Cottage costs around £330 per night.

How many holiday homes are available to rent in Chepstow?

There are 150 holiday rentals from 8 providers on offer in Chepstow.

What is the most searched holiday home amenity in Chepstow?

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

How many holiday homes in Chepstow have a pool?

Holiday homes with pools are 14 of all offers in Chepstow. In addition, there are 5 of rentals with pools near water.

Can i bring my pet during my stay in an accommodation in Chepstow?

There are 41 holiday homes in Chepstow that allow pets with an average price of £182 per night.

What's the perfect time to travel to Chepstow?

Sun lovers should visit Chepstow in July and August to enjoy the warmest weather.

How do I find discounts on holiday accommmodation in Chepstow?

You can find brilliant bargains on holiday accommodation in Chepstow with the nightly price of a rental starting at just £50 - and HomeToGo has introduced plenty of features that mean it's a piece of cake to locate the top offers. When considering different dates for your break, try a search using HomeToGo's flexible dates technology to quickly locate low-price date options and find savings of up to 10%. Moreover, HomeToGo's 'distance from' filter makes it easy to see hidden treasure holiday rentals in great value, under-the-radar locales with good proximity to your desired destination, whether that's sand and sea, a mountain for snowboarding, or a city's urban hub. Book early to take advantage of good availability and low prices - and do so free from stress by using HomeToGo's 'free cancellation' filter when using the website or app.

What are the benefits of booking 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 have a variety of bonuses. HomeToGo lets you read genuine ratings from verified visitors, and searching is secure, simple, and stress-free - so with 150 lets from 8 providers in the vicinity, you're guaranteed to find the right type of accommodation with the amenities and features to suit you in Chepstow.

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