Chepstow Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to €185 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Chepstow

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 €97 per night from 31 Aug to 1 Sept
€97
31 Aug - 1 Sept
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"The staff were very friendly and helpful. The room itself was adequate. Some areas could have done with a better clean. Dirty windows, bath in the corners, wasn't very clean and if you lay in the bath, you could see only tops have been cleaned and not the undersides The bed was comfortable, however, ..."

Reviewed on 7 Aug 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 €124 per night from 12 Aug to 13 Aug
€124
12 Aug - 13 Aug
includes taxes & fees
8.2/10 Very Good! (1,299 reviews)
"Fabulous stay as always"

Reviewed on 6 Aug 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 €87 per night from 17 Aug to 18 Aug
€87
17 Aug - 18 Aug
includes taxes & fees
9.2/10 Wonderful! (1,443 reviews)
"Easy access to the city, quiet hotel and very safe for female travellers"

Reviewed on 7 Aug 2025

Hotel Indigo Cardiff by IHG
See all 3,170 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.

Popular places to visit

Millennium Stadium showing 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 heritage elements, château or palace and heritage architecture

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

Cardiff: City Highlights Guided Walking Tour

Cardiff: City Highlights Guided Walking Tour

€20
per adult
Cardiff: City Highlights Guided Walking Tour
Cardiff Bay Boat Tour

Cardiff Bay Boat Tour

€15
per adult
74% of travellers recommend
Cardiff Bay Boat Tour
From Cardiff: Guided Tour of Welsh Valleys

From Cardiff: Guided Tour of Welsh Valleys

€104
per adult
100% of travellers recommend
From Cardiff: Guided Tour of Welsh Valleys
See all activities in Chepstow

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?

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