
Chepstow Vacations from $915
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Find the right fit
Rest easy
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

Bristol Grand Hotel By Sunday
Reviewed on Aug 18, 2025

Montigo Resorts, Somerset
Reviewed on Jun 2, 2025

Bristol Marriott Royal Hotel
Reviewed on Aug 23, 2025

The Bristol Hotel
Reviewed on Aug 24, 2025

Discover the most popular places to visit in Chepstow

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.

Cardiff Bay
Explore the waterfront in Cardiff with a trip to Cardiff Bay. Discover the top-notch restaurants and acclaimed theater scene in this relaxing 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

From Cardiff: Guided Tour of Welsh Valleys
Chepstow Hotel Deals

Delta Hotels by Marriott St. Pierre Country Club
Reviewed on Aug 22, 2025

Celtic Manor Resort
Reviewed on Aug 21, 2025

Delta Hotels by Marriott Bristol City Centre
Reviewed on Aug 21, 2025