Holidays to Chepstow

Choose two or more items and save on your trip:
Choose two or more items and save on your trip:

Hotels, flights, car hire & activities - all in one place! Bundle everything you need for your holiday to Chepstow and save

Top Hotel Deals

Two Rivers, Chepstow by Marston’s Inns
Two Rivers, Chepstow by Marston’s Inns
4 out of 5
Newport Road, Chepstow, Wales
The price is £52 per night from 30 Jan to 31 Jan
Situated in Chepstow, this inn is within 1 mi (2 km) of Chepstow Castle and Wye Valley. Chepstow Racecourse is 1.3 mi (2.1 km) away. Chepstow Station is 13 minutes ...
4.4/5 Excellent! (104 reviews)
"Brand new very good easy parking nice staff good food from on site pub good value for money In all 10/10"

Reviewed on 4 Dec 2021

Two Rivers, Chepstow by Marston’s Inns
St Pierre Marriott Hotel & Country Club
St Pierre Marriott Hotel & Country Club
4 out of 5
The price is £84 per night from 15 Feb to 16 Feb
Situated on a lake, this spa hotel is 3.1 mi (4.9 km) from Chepstow Castle and 3.1 mi (5 km) from Wye Valley. Chepstow Racecourse and Caldicot Castle are also ...
4.1/5 Very Good! (731 reviews)
"We had a couple off problems with the room but they were sorted for the second night"

Reviewed on 20 Dec 2021

St Pierre Marriott Hotel & Country Club
The Wild Hare
The Wild Hare
4 out of 5
The price is £120 per night from 9 Feb to 10 Feb
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 Chepstow Castle. Wye Valley and ...
4.7/5 Exceptional! (35 reviews)
"This is a family run hotel with a big welcome. It is in a beautiful spot in the Wye Valley. We will definitely be coming again."

Reviewed on 14 Nov 2021

The Wild Hare
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.

Frequently asked questions

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.