Chepstow Holidays
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Chepstow Holiday
Our pick of the best Chepstow Hotel Deals
Delta Hotels by Marriott St. Pierre Country Club
St Pierre Park Chepstow Wales
Fully refundableReserve now, pay when you stay
NZ$232
10 Sept - 11 Sept
includes taxes & fees
Delta Hotels by Marriott Bristol City Centre
2 Lower Castle Street Bristol England
Fully refundableReserve now, pay when you stay
NZ$154
27 Sept - 28 Sept
includes taxes & fees
8.8/10 Excellent! (823 reviews)
"Great location, lovely hotel… just a little more basic than I was expecting"
Reviewed on 4 Sept 2026
Celtic Manor Resort
Chepstow Road Newport Wales
NZ$312
11 Sept - 12 Sept
includes taxes & fees
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.
Stay near popular Chepstow attractions
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.
Photo by Miguel Vasquez
Chepstow Castle
9.0/10 (29 reviews)
Chepstow Castle is the oldest surviving stone fort in Britain and easily one of the most spectacular castles in Wales. The impressive castle dates back to the Norman invasion and perches precariously atop a cliff on the banks of the River Wye. Any visit is sure to invoke plenty of awe and wonder.
Chepstow Racecourse
9.0/10 (26 reviews)
Chepstow Racecourse is situated in Monmouthshire in south-east Wales, near the southern end of the Wye Valley. The track is a great point of interest in the UK and attracts visitors from all over the world.
St. Pierre Country Club
7.6/10 (17 reviews)
Enjoy a round of golf in Mathern at St. Pierre Country Club. Visit the shops and top-notch restaurants in this walkable area.
Symonds Yat Rock
9.6/10 (7 reviews)
Commune with nature and explore the great outdoors at Symonds Yat Rock during your travels in Tidenham. Make time for the spas and golf courses in this family-friendly area.
Parva Farm Vineyard
10.0/10 (2 reviews)
You can enjoy a tasting or tour at Parva Farm Vineyard during your travels to Tintern. Visit the spas and top-notch restaurants in this relaxing area.
Caerwent Roman Town
6.0/10 (2 reviews)
You can learn about the history of Newport with a visit to Caerwent Roman Town. Make time for the spas and golf courses in this relaxing area.
Offa's Dyke National Trail - Southern Terminus
9.0/10 (7 reviews)
You can take time to visit Offa's Dyke National Trail - Southern Terminus during your travels to Tidenham.
What to do in Chepstow
Cardiff: Alcotraz Immersive Prison Cocktail Experience
NZ$135
per adult
Cardiff/Swansea: Gower Peninsula's Cliffs & Mumbles Day Tour
NZ$187
per adult
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?
- 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.
- 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.
- 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.
- 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.
