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$172 per night from 6 Apr to 7 Apr
AU$172
includes taxes & fees
6 Apr - 7 Apr
8.2/10 Very Good! (1,000 reviews)
"Whilst on this occasion things didn’t go as planned, I still couldn’t fault the staff on the way they sorted the issue quickly and generously. It was a trip away for my birthday and everyone went out of their way to make my stay memorable for all the right reasons. Amazing food, delightful surroundings, ..."

Reviewed on 10 Mar. 2025

Delta Hotels by Marriott St. Pierre Country Club
Delta Hotels by Marriott Bristol City Centre
Delta Hotels by Marriott Bristol City Centre
4 out of 5
2 Lower Castle Street, Old Market, Bristol, England
Fully refundableReserve now, pay when you stay
The price is AU$145 per night from 6 Apr to 7 Apr
AU$145
includes taxes & fees
6 Apr - 7 Apr
8.6/10 Excellent! (232 reviews)
Girls wkend away
"Fantastic hotel had an upgrade from a twin to two double beds in room, lovely bedding great facilities ideal for town centre too."

Reviewed on 10 Mar. 2025

Delta Hotels by Marriott Bristol City Centre
Bristol Marriott Royal Hotel
Bristol Marriott Royal Hotel
4 out of 5
College Green, Bristol, England
Fully refundableReserve now, pay when you stay
The price is AU$172 per night from 23 Mar to 24 Mar
AU$172
includes taxes & fees
23 Mar - 24 Mar
9/10 Wonderful! (1,036 reviews)
Lovely hotel
"Amazing staff throughout"

Reviewed on 17 Mar. 2025

Bristol Marriott Royal Hotel
See all 3,130 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

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.

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
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
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

What to do in Chepstow

From Cardiff: Guided Tour of Welsh Valleys

From Cardiff: Guided Tour of Welsh Valleys

AU$180
per adult
100% of travellers recommend
From Cardiff: Guided Tour of Welsh Valleys
Cardiff: City Highlights Guided Walking Tour

Cardiff: City Highlights Guided Walking Tour

AU$34
per adult
Cardiff: City Highlights Guided Walking Tour
Make a bottle of gin or rum at our distillery

Make a bottle of gin or rum at our distillery

AU$162
per adult
Make a bottle of gin or rum at our distillery
See all activities in Chepstow
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.