Chepstow Holidays
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Top hotels in Chepstow
Delta Hotels by Marriott St. Pierre Country Club
St Pierre Park Chepstow Wales
Fully refundableReserve now, pay when you stay
S$173
20 Sept - 21 Sept
includes taxes & fees
Delta Hotels by Marriott Bristol City Centre
2 Lower Castle Street Bristol England
Fully refundableReserve now, pay when you stay
S$115
27 Sept - 28 Sept
includes taxes & fees
8.8/10 Excellent! (827 reviews)
"Great location, close parking and comprehensive buffet restaurant. Really need to get the third elevator fixed, you spend a lot of time waiting for the elevator."
Reviewed on 13 Sept, 2026
Celtic Manor Resort
Chepstow Road Newport Wales
Fully refundableReserve now, pay when you stay
S$235
20 Sept - 21 Sept
includes taxes & fees
8.6/10 Excellent! (1,421 reviews)
"Beautiful hotel. Nice spa with steam and Sauna. Very wonderful views"
Reviewed on 14 Sept, 2026
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)
The monastic ruins of Tintern Abbey are nestled in the heart of the Wye Valley area of outstanding natural beauty and can boast 900 years of history in their walls. This was the first Cistercian abbey built in Wales and only the second in Britain, and despite now being exposed to the elements, it remains one of the most stunning surviving examples of gothic architecture in the country.
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/Swansea: Gower Peninsula's Cliffs & Mumbles Day Tour
S$138
per adult
Cardiff: South Wales Cliffs, Beaches & Castles Day Tour
S$138
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
