Chepstow Vacations from $1,281
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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.
The Latest Chepstow vacation packages
Price found within the past 48 hours. Click for updated prices.
YourApartment Cotham Arms
$1,281
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bristol (BRS)
8.4/10 Very Good! (12 reviews)
Upon arrival the room was relatively clean and straightened out nicely. Decorated to an OK standard.
However, the room itself was absolutely sweltering and could've done with a fan or a portable air conditioning unit. I had to open both the windows wide to let some cool air in.....which unfortunately let the screaming and shouting from outside in too. But hey, I've booked something in the heart of student land so that's sort of on me as well!
As far as cleanliness goes....look a little closer you'll see things aren't so great and definitely lacks attention to detail in that are. Not the worst but certainly not the best.
It looks like shower gel, handwash and shampoo were provided once upon a time but now all that remain are empty containers. This is such a basic thing so either do it or don't.
Kitchenette area was reasonably clean with utensils, plates bowls and a dishwasher provided.
Overall, it was OK but could do better. It seems like somebody has lost interest in it!
Reviewed on Sep 21, 2025
The Royal Oak Exmoor
$1,681
per person
Sep 8 - Sep 14
found 5 hours ago
Roundtrip flight included
Miami (MIA) to Bristol (BRS)
9.8/10 Exceptional! (54 reviews)
Gorgeous property with excellent facilities. Staff were absolutely incredible - friendly, welcoming and highly competent. Could not recommend this place enough!
Reviewed on Aug 4, 2026
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 lively bars 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.
Gate House
10.0/10 (4 reviews)
You can learn about the history of Chepstow with a trip to Gate House. Check out the spas and top-notch restaurants in this walkable 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.
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 charming coffeehouses in this family-friendly area.
What to do in Chepstow
Cardiff: Gower Peninsula's Cliffs & Mumbles Scenic Day Tour
$113
per adult
The Wandering Bard's Mythical West Wales Tour
$114
per adult
100% of travellers recommend
Cardiff: South Wales Cliffs, Beaches & Castles Day Tour
$113
per adult
Chepstow Hotel Deals
Delta Hotels by Marriott St. Pierre Country Club
St Pierre Park Chepstow Wales
Fully refundableReserve now, pay when you stay
$104 nightly
$125 total
Aug 31 - Sep 1
Total with taxes and fees
8.2/10 Very Good! (1,004 reviews)
"The welcome from reception was 💯, the room was on first appearance very nice, then as time went on we started seeing imperfections, dust spiders were everywhere in all corners and crevices and whilst trying to kill a fly on the curtains the dust that came off them filled the room, rubbish left around ..."
Reviewed on Aug 2, 2026
Celtic Manor Resort
Chepstow Road Newport Wales
Fully refundableReserve now, pay when you stay
$122 nightly
$147 total
Aug 26 - Aug 27
Total with taxes and fees
Clayton Hotel Bristol City
Broad Street Bristol England
Fully refundableReserve now, pay when you stay
$98 nightly
$117 total
Aug 16 - Aug 17
Total with taxes and 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.
Find the Best Chepstow Vacation Packages
Chepstow Essential Information
Language | Welsh |
|---|---|
Currency | British pounds sterling |
Population | 16,200 |
Max Temp Winter | 45ºF |
Max Temp Summer | 65ºF |
Top Sights | Chepstow Castle, Chepstow Castle and Caldicot Castle |
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Frequently asked questions
How much does a Chepstow vacation package cost?
Offering excellent value package deals from $1,281 on Expedia, you'll be thrilled with how little a vacation to Chepstow costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Chepstow?
If you'd like to snag a cheap Chepstow vacation package, consider traveling in August, November and December. You'll usually find lower prices on accommodations and flights during these months — perfect for a budget-friendly getaway.
How many days is enough for Chepstow?
We recommend booking a Chepstow vacation for a minimum of 2 days. This will allow you enough time to check off major attractions such as Chepstow Museum and Parva Farm Vineyard, and also explore neighborhoods like Portskewett and Devauden. You might even be able to fit in a day trip (or two) from Chepstow.
Is it worth booking a vacation package to Chepstow?
From attractions such as Chepstow Racecourse and Chepstow Castle to its epic history, a Chepstow vacation offers a vibrant mix of experiences. With so much to do and see, it's time to find out for yourself why Chepstow is such a good vacation destination.
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 vacation package as soon as possible.
Is it cheaper to book a Chepstow vacation as a package?
You can enjoy significant savings on your Chepstow escape by booking a customized vacation 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 vacation 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 go: Check your calendar and pack your bags. Your preferred time of year and the type of activities available will also help you decide when to escape to Chepstow.
- Calculate your budget: Make sure you have enough money to cover everything from dining out and transportation to flights and activities. Your accommodations will probably be the biggest expense during your trip to Chepstow.
- Use Expedia's trip planning tool to explore Chepstow: Research every aspect of your trip to Chepstow with this handy planner. Invite your friends and family to collaborate on a group getaway, search for hotels or things to do and make bookings.
- Decide how long to go for: Now that you're more familiar with Chepstow, you can work out the ideal length of your break. Pull together a draft plan and give yourself enough time to cover everything you want to do.
- Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a tailored Chepstow vacation package.
- Book experiences or activities in advance: Whether it's entrance to a major attraction or a walking tour, you won't have to worry about missing out on the highlights of Chepstow. Find all the fun things to do in Chepstow with our dedicated travel guide.
Does Expedia offer Book Now, Pay Later Chepstow vacation packages?
Set off on your dream escape to Chepstow with our Book Now, Pay Later vacations. There's no need to scrimp and save or wait for your next payday — we've teamed up with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans allow you to spread the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, you can easily budget for your trip and snap up travel deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
