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
The price is AU$172 per night from 31 Aug to 1 Sept
AU$172
31 Aug - 1 Sept
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"Beautiful buildings and setting when you first arrive driving through the golf course. I had previously asked for an early check in as we were attending a wedding off site, however they did not manage that for us, so we stored our bags and checked in on our return from the wedding. Breakfast was ..."

Reviewed on 1 Aug. 2025

Delta Hotels by Marriott St. Pierre Country Club
Celtic Manor Resort

Celtic Manor Resort

5 out of 5
Chepstow Road, Coldra Wood, Newport, Wales
Fully refundableReserve now, pay when you stay
The price is AU$202 per night from 7 Aug to 8 Aug
AU$202
7 Aug - 8 Aug
includes taxes & fees
8.2/10 Very Good! (1,293 reviews)
"This is a gem of a place! Thoroughly enjoyed the stay and the experience. Great staff who are welcoming! Definitely coming back again!"

Reviewed on 27 Jul. 2025

Celtic Manor Resort
Hotel Indigo Cardiff by IHG

Hotel Indigo Cardiff by IHG

4 out of 5
Dominions Arcade Queen Street, Glamorgan, Cardiff, Wales
Fully refundable
The price is AU$164 per night from 1 Sept to 2 Sept
AU$164
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (1,432 reviews)
City Centre Gem
"Perfect location right in the city centre. Modern & clean with friendly staff. Unique layout due to the building it's in. NCP car park a couple of hundred metres away round the back, with generous discount scheme. Our only complaint was that the windows don't open at all. The A/C was efficient and ..."

Reviewed on 4 Aug. 2025

Hotel Indigo Cardiff by IHG
See all 3,165 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.
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Discover the most popular places to visit in Chepstow

Millennium Stadium showing a river or creek and modern architecture

Principality Stadium

4/5(6 reviews)

Follow in the footsteps of sporting and musical greats when you tour this vast sporting arena. Walk on the pitch, see dressing rooms and lift a trophy.

Principality Stadium
Barry Island Beach

Barry Island Beach

3/5(2 reviews)

If you’re looking for a quintessential Welsh seaside experience, look no further than Barry Beach in the picturesque Vale of Glamorgan.

Barry Island Beach
Cardiff Castle showing heritage architecture, château or palace and heritage elements

Cardiff Castle

4.5/5(28 reviews)

A fortified tower from the 12th century, World War II tunnels and Welsh military history make a fascinating day out at this magnificent castle.

Cardiff Castle

What to do in Chepstow

A tour arrives at Caerleon.

The Wandering Bard's Valley Tour or the Swansea Bay Tour.

AU$184
per adult
The Wandering Bard's Valley Tour or the Swansea Bay Tour.
Pembroke Castle.

The Wandering Bard's Mythical West Wales Tour

AU$192
per adult
The Wandering Bard's Mythical West Wales Tour
Cardiff Bay Boat Tour

Cardiff Bay Boat Tour

AU$26
per adult
74% of travellers recommend
Cardiff Bay Boat 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.

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