Chepstow Vacation Packages

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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.

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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 CA $128 per night from Aug 31 to Sep 1
CA $128
CA $154 total
Aug 31 - Sep 1
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"Our room was spacious and had a balcony on the lake which was lovely. All staff on reception, in the spa and at breakfast were friendly and warm. Breakfast was good, usual buffet style. All round good value and pleasant stay."

Reviewed on Aug. 4, 2025

Delta Hotels by Marriott St. Pierre Country Club
Celtic Manor Resort

Celtic Manor Resort

5 out of 5
Chepstow Road, Coldra Wood, Newport, Wales
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from Aug 27 to Aug 28
CA $150
CA $181 total
Aug 27 - Aug 28
includes taxes & fees
8.2/10 Very Good! (1,293 reviews)
"This is a gem of a place! Thoroughly enjoyed the stay and the experience. Great staff who are welcoming! Definitely coming back again!"

Reviewed on Jul. 27, 2025

Celtic Manor Resort
Hotel Indigo Cardiff by IHG

Hotel Indigo Cardiff by IHG

4 out of 5
Dominions Arcade Queen Street, Glamorgan, Cardiff, Wales
Fully refundable
The price is CA $115 per night from Aug 10 to Aug 11
CA $115
CA $139 total
Aug 10 - Aug 11
includes taxes & fees
9.2/10 Wonderful! (1,438 reviews)
"Excellent hôtel, warm Welsh attention, comfortable and élégant. Very nice and complete breakfast!"

Reviewed on Aug. 4, 2025

Hotel Indigo Cardiff by IHG
See all 3,164 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 Vacations
All Inclusive Vacations
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Discover the most popular places to visit in Chepstow

Millennium Stadium which includes modern architecture and a river or creek

Principality Stadium

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
Barry Island Beach

Barry Island Beach

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
Cardiff Castle featuring château or palace, heritage architecture and heritage elements

Cardiff Castle

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

What to do in Chepstow

A tour arrives at Caerleon.

The Wandering Bard's Valley Tour or the Swansea Bay Tour.

CA $166
per adult
The Wandering Bard's Valley Tour or the Swansea Bay Tour.
Cardiff Bay Boat Tour

Cardiff Bay Boat Tour

CA $24
per adult
74% of travellers recommend
Cardiff Bay Boat Tour
Cardiff: Doctor Who City Walking Tour

Cardiff: Doctor Who City Walking Tour

CA $31
per adult
Cardiff: Doctor Who City Walking Tour
See all activities in Chepstow

Frequently asked questions

How much does a Chepstow vacation package cost?
Offering excellent value package deals 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.