Chepstow Holidays

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Your Chepstow Holiday

The hassle-free way to experience this interesting city is with a tailor-made Chepstow holiday package. Base yourself in the neighbourhood of Trellech United, which is good for culture, nature and history or go someplace else — our packages are all about you. If sightseeing is part of the plan during your trip to Chepstow, swing by top attractions like Chepstow Racecourse, Tintern Abbey and Chepstow Castle. Whoever you're taking a break with and whatever your budget, your dream Chepstow holiday is just a few clicks away with Expedia.

Chepstow Holiday

Chepstow Essential Information

Language
Welsh
Currency
British pounds sterling
Closest Airport
Bristol Intl. Airport (BRS)
Population
16,200
Max Temp Winter
7ºC
Max Temp Summer
18ºC
Top Sights
Berkeley Castle, Chepstow Castle and Caldicot Castle

Our pick of the best Chepstow Hotel Deals

Delta Hotels by Marriott St. Pierre Country Club

Delta Hotels by Marriott St. Pierre Country Club

4 out of 5
St Pierre Park Chepstow Wales
Fully refundableReserve now, pay when you stay
The price is AU$195 per night from 30 July to 31 July
AU$195
30 July - 31 July
includes taxes & fees
8.2/10 Very good! (1,004 reviews)
"I'm not massively impressed by this hotel. I picked it out because of the main shot of the front that you'll likely see over any promo material. And that's awesome, but you're not staying there really. I mean there are the courtyard facing rooms and I would recommend these if you want the full experience, ..."

Reviewed on 11 July 2026

Delta Hotels by Marriott St. Pierre Country Club
Mollie's Bristol

Mollie's Bristol

4 out of 5
Cribbs Causeway Bristol England
The price is AU$134 per night from 2 Aug to 3 Aug
AU$134
2 Aug - 3 Aug
includes taxes & fees
9.4/10 Exceptional! (2,107 reviews)
"NA"

Reviewed on 11 July 2026

Mollie's Bristol
Clayton Hotel Bristol City

Clayton Hotel Bristol City

4 out of 5
Broad Street Bristol England
Fully refundableReserve now, pay when you stay
The price is AU$168 per night from 26 July to 27 July
AU$168
26 July - 27 July
includes taxes & fees
9.2/10 Wonderful! (1,400 reviews)
"The room was great, clear and nice and cool. Breakfast was also delicious and you can choose from many items. Staff was super friendly and nice too"

Reviewed on 11 July 2026

Clayton Hotel Bristol City
See all 3,687 properties in Chepstow
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Stay near popular Chepstow attractions

A historic stone cathedral with large arches and Gothic windows.

Tintern Abbey

9.6/10 (60 reviews)
Tour the ruins of an ancient monastery where Cistercian monks used to live, pray and study. See the remains of their former dwellings and church.
See properties

What to do in Chepstow

From Barry Island: Gavin and Stacey Tour

From Barry Island: Gavin and Stacey Tour

AU$86
per adult
From Barry Island: Gavin and Stacey Tour
Cardiff: Gower Peninsula's Cliffs Scenic Day Tour

Cardiff: Gower Peninsula's Cliffs & Mumbles Scenic Day Tour

AU$164
per adult
Cardiff: Gower Peninsula's Cliffs & Mumbles Scenic Day Tour
Cardiff: Doctor Who City Walking Tour

Cardiff: Doctor Who City Walking Tour

AU$38
per adult
Cardiff: Doctor Who City Walking Tour
See all activities in Chepstow

Frequently asked questions

How much does a Chepstow holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday to Chepstow costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Chepstow?
Plan your getaway for the shoulder or low season and you're likely to score cheap Chepstow holiday packages. Remember that public holidays and major festivals and events can have an impact on prices, so do your research before you go.
How many days is enough for Chepstow?
Chepstow holidays can be as short or long as you like, but to really sink your teeth into this destination, we'd suggest 2 days is about right. This will mean you can fit in top attractions like Chepstow Museum and Parva Farm Vineyard and track down some lesser-known gems. Don't skip cool neighbourhoods such as Portskewett and Devauden either. If you're clever with your time, you can even take a day trip or two from Chepstow too.
Is it worth booking a holiday package to Chepstow?
Well known for its history and home to popular attractions like Chepstow Castle, a Chepstow holiday is sure to leave an impression. Another top sight worth exploring? Don't miss Symonds Yat Rock.
How to find the best Chepstow package deals?
Use Expedia's filters to help you find some unbeatable Chepstow package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Chepstow package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your holiday package as soon as possible.
Is it cheaper to book a Chepstow holiday as a package?
You can enjoy significant savings on your Chepstow escape by booking a customised holiday package. Click on the "Package" heading, then enter your travel dates and destination to browse the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to Chepstow?
If you're considering a spontaneous Chepstow getaway, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Chepstow?

  1. Choose when to travel: Check your calendar and get your bags packed. Your preferred time of year and the available activities will also help you decide when to escape to Chepstow.
  2. Plan your budget wisely: In addition to the price of your accommodation, you should consider other expenses. These include food, transportation and flights. Also, set aside some extra funds for unexpected costs that may arise during your trip to Chepstow.
  3. Decide how many days away: Start by listing all the activities and attractions you want to get to in Chepstow. Then, estimate how long you'll need at each, including any travel time.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to choose a Chepstow holiday package that brings all your bookings together.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.