
Chepstow Holidays from £340
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Top Chepstow Flight + Hotel Deals

The Washington
Reviewed on 14 Jul 2025

Alison Court
Reviewed on 13 Oct 2023

Beech House
Reviewed on 16 May 2025

Top hotels in Chepstow

Delta Hotels by Marriott St. Pierre Country Club
Reviewed on 6 Jul 2025

Delta Hotels by Marriott Bristol City Centre
Reviewed on 15 Jul 2025

Celtic Manor Resort
Reviewed on 12 Jul 2025
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.
Popular places to visit

Principality Stadium
The spiritual home of Welsh rugby, the Principality Stadiumin Cardiff is one of the most famous sporting arenas on the planet, envied the world over for its cauldron-like atmosphere and state-of-the-art facilities.

Cardiff Bay
Explore the waterfront in Cardiff with a trip to Cardiff Bay. Discover the lively bars and acclaimed theatre scene in this walkable area.

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.
What to do in Chepstow

Cardiff: City Highlights Guided Walking Tour

Cardiff: Waterfalls, Three Castles & Mountains Day Tour
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.