Chepstow Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Chepstow Vacation
When a city break is calling, answer it with a vacation package to Chepstow. The neighborhood of Trellech United, which is great for culture, nature and history, makes a fantastic base for your adventures. If your trip to Chepstow includes some sightseeing, visit renowned attractions like Chepstow Racecourse, Tintern Abbey and Chepstow Castle. Expedia has what you need to escape your routine. Tailor your vacation to Chepstow to match your travel style, whatever that may look like.
Top Chepstow Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Old Bell Hotel
CA $1,562
per person
Nov 26 - Dec 1
found 2 hours ago
Roundtrip flight included
Calgary (YYC) to Bristol (BRS)
9.4/10 Exceptional! (321 reviews)
We enjoyed a beautiful experience at this Hotel. Location and history was perfect. We had a delicious dinner that was prepared perfectly. Staff were very helpful for the short time we were there!
Reviewed on Oct 4, 2026
Lucknam Park, Emblems Collection
CA $2,050
per person
Nov 28 - Dec 1
found 22 hours ago
Roundtrip flight included
Calgary (YYC) to Bristol (BRS)
9.6/10 Exceptional! (214 reviews)
A little late writing this review but I stayed at the Lucknam with my wife for our Babymoon in May this year and it was wonderful. The staff were incredible from the moment we arrived. They were considerate with the room choice, made sure to provide everything we asked for and more and were generally the nicest team of staff we have met.
The hotel was beautiful, Restaurants were excellent and so was the Spa. Life has been a blur since the baby so apologies for not remembering any names at 1am but thank you Lucknam team. We shall be back❤️
Reviewed on Oct 5, 2026
Ready to book your vacation to Chepstow?
Chepstow Hotel Deals
Delta Hotels by Marriott St. Pierre Country Club
St Pierre Park Chepstow Wales
Fully refundableReserve now, pay when you stay
CA $159
CA $191 total
Oct 25 - Oct 26
includes taxes & fees
Delta Hotels by Marriott Bristol City Centre
2 Lower Castle Street Bristol England
Fully refundableReserve now, pay when you stay
CA $111
CA $134 total
Oct 25 - Oct 26
includes taxes & fees
Clayton Hotel Bristol City
Broad Street Bristol England
Fully refundableReserve now, pay when you stay
CA $123
CA $148 total
Nov 8 - Nov 9
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. Check out 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. Check out 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 trip 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
CA $150
per adult
The Valleys tour or Swansea Bay tour. Please choose correctly.
CA $150
per adult
100% of travellers recommend
Frequently asked questions
How much does a Chepstow vacation package cost?
Offering excellent value package deals from CA $1,482 on Expedia, you'll be pleasantly surprised at how much a vacation to Chepstow costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Chepstow?
Plan your trip for the off-peak season and you're likely to find cheap Chepstow vacation packages. Keep in mind that public holidays and major festivals and events can have an impact on prices, so do a little research before you go.
How many days is enough for Chepstow?
Chepstow vacations come in various shapes and sizes, but to really get a feel for this destination, we'd say 2 days is about right. With this timeframe, you can fit in top sights like Caldicot Castle and Symonds Yat Rock along with lesser-known spots. Don't forget to explore cool areas such as Portskewett and Devauden either. If you're smart with your time, you can even allow for a day trip or two from Chepstow too.
Is it worth booking a vacation package to Chepstow?
Known for its history and home to popular attractions like Chepstow Castle, a Chepstow vacation is sure to impress. Another top sight worth exploring? Don't miss Symonds Yat Rock.
How to find the best Chepstow package deals?
Landing a cheap Chepstow package deal is a cinch with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget range, apply a couple of filters and see what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Chepstow package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Chepstow vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and accommodations individually. Better still, you can tailor your Chepstow trip to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Chepstow?
If you're planning a spur-of-the-moment Chepstow vacation, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Chepstow?
- Choose when to travel: Check your diary and get packing. Your favourite time of year and the activities on offer will also help you decide when to escape to Chepstow.
- Calculate your budget: Ensure you have enough money to pay for everything from dining out and transportation to experiences and flights. Your accommodations will likely be the biggest expense during your trip to Chepstow.
- Decide how many days away: Start by compiling a list of the sights and activities you'd like to experience in Chepstow. Then, estimate how long you'll need at each, including any travel time.
- Combine your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to find a Chepstow vacation 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.
