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Holidays to Chepstow

Choose two or more items and save on your trip:

Accommodation, flights, car rentals, things to do and more - for your holiday in Chepstow choose Expedia! Find everything you need to organise your trip to Chepstow in one place. Enter your dates in the search bar above or scroll to our top deals below!

Top Hotel Deals

St Pierre Marriott Hotel & Country Club
St Pierre Marriott Hotel & Country Club
4 out of 5
The price is £88 per night from 12 Feb to 13 Feb

Situated on a lake, this spa hotel is 0.1 mi (0.2 km) from Saint Pierre Park and 3.1 mi (5 km) from Wye Valley. David Broome Event Centre and Chepstow Castle ...

4.1/5Very Good! (658 reviews)

"The staff is absolutely kind and helpful, obviously for covid everything is up side down. I mean. The menu is reduce but is normal. The town is 7 mins drive and is fine. You can order take aways as well. The room definitely needs an upgrade but it was very spacious. We enjoyed our stay. And we book ..."…"

Reviewed on 4 Oct 2020

St Pierre Marriott Hotel & Country Club
3.5 out of 5
The price is £115 per night from 31 Jan to 1 Feb

Situated in Chepstow, this cottage is within 3 miles (5 km) of Chepstow Castle, Wye Valley and Chepstow Racecourse. Offa's Dyke National Trail - Southern Terminus ...

4.7/5Exceptional! (14 reviews)

"Stunning cottage, 5 mins from centre of Chepstow. Fantastic host. Had 2 boys with us who loved the use of the pool table. Couldn’t fault it."…"

Reviewed on 22 Aug 2020

The Royal George Tintern
The Royal George Tintern
4 out of 5

Situated in Chepstow, this hotel is 0.2 mi (0.4 km) from Tintern Abbey and within 6 miles (10 km) of Chepstow Racecourse and Wye Valley. St Mary's Priory Church ...

4.7/5Exceptional! (23 reviews)
Wonderful hotel in Tintern

"Wonderful welcome especially for our four-legged friend Archie. Beautiful room with a box of treats for the dog (biscuits, bowl, a ball and poop bags). Very comfortable room with a dog bed. Delicious dinner in the Wild Hare. Service was good and, again, they looked after Archie with some leftover ..."…"

Reviewed on 20 Oct 2020

The Royal George Tintern
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.

Top things to do in Chepstow

The Advantages of Chepstow Weekend Breaks

Discover a different side of the British Isles with a weekend break in Chepstow. Take short breaks away from home and enjoy some quality time in a beautiful place. You’ll come back feeling refreshed and inspired. You can have an action-packed Chepstow weekend break or get some peace with a relaxing holiday. Whatever experience you’re looking for, find it with our deals on hotels in Chepstow.

Cheap Weekend Breaks to Chepstow

There are lots of ways to take cheap weekend breaks to Chepstow. Expedia offers deals on car hires and hotel rooms and covers trips for all kinds of travellers. The best way to save is with our holiday packages in Chepstow. First, choose your car hire and hotel reservation. Then we’ll bundle them together into one discounted price. Solo explorers, couples, families, and groups of friends can discover budget solutions for their weekend breaks. Once you arrive, enjoy some of the fun things to do, many of which are free or cheap to experience  

Chepstow Romantic Weekend Breaks

Couples love taking romantic weekend breaks in Chepstow. Whisking your lover away for a romantic Chepstow weekend break is the perfect opportunity to make new memories together. Expedia offers all kinds of hotel options, so you can find romantic hotels in Chepstow and choose the best place for you. Check out our deals on beautiful properties, and you’ll save even more when you choose to package your hotel reservation with a car hire. 

Family Weekend Breaks in Chepstow

Set some time aside to experience family weekend breaks in Chepstow. There are plenty of excellent family-friendly hotels in Chepstow within our selection of hotels. You can also find a place to call home in one of the holiday rentals in Chepstow. With accommodation, activities, and adventure all waiting, there’s never been a better time to plan Chepstow family weekend breaks. 

Plan your Chepstow holiday with Expedia

  • Book your 2021 holiday package deals now! Buy your accommodation, flight or car together and get extra savings on your next trip!
  • We have selected for you amazing deals on incredible hotels in Chepstow. Have a look simply by using the search bar above.
  • Most hotels come with free cancellation, because we believe that flexibility matters now more than ever!

For more information, visit our COVID-19 information page
Start browsing now!

*Some hotels require you to cancel at least 24-48 hours before check-in.

Frequently asked questions

If I'm not able to travel, can I cancel my Chepstow holiday package?
Because we understand life can be unpredictable, the answer is yes. For further details, visit our Customer Service Portal. But generally speaking, if you’ve booked your package in the last 24 hours, you may be able to cancel or change it without penalty. Your hotel, airline or car rental company may impose a fee if you made your booking a while ago.
When is the best time of year to visit Chepstow?
August, July, June is known as the busy season in Chepstow, while February, January , December is generally a lot quieter. If you’re searching for a great deal on your trip, consider the month of November. It’s also worth keeping in mind that June is usually the most expensive time of year to visit.
How far in advance should I book my Chepstow holiday?
Travellers are generally able to browse international airfares on Expedia up to a year in advance of departure. Booking late? With a stroke of luck, there’s a still a chance you can purchase a cheap ticket just weeks before your journey.
What should I know before booking a Chepstow travel package?
You can save big by combining your airfares, hotels and rental cars. Once you’ve made your booking, you can add on sightseeing tours or experiences. Your next unforgettable holiday is only a few clicks away.
Does Expedia offer Book Now, Pay Later Chepstow holiday packages?
Thanks to the joint efforts of Expedia and online lender Affirm, you can spread the cost of your package booking over a number of payments. For financial freedom, look up our Book Now, Pay Later option and work out a payment plan that meets your needs.