Chepstow Vacations from US$ 858
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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
Price found within the past 48 hours. Click for updated prices.
Spinneycross
Price was US$ 869, price is now US$ 858 per person
US$ 858
per person
Mar 25 - Mar 29
found 23 hours ago
Roundtrip flight included
New York (NYC) to Bristol (BRS)
9.8/10 Exceptional! (119 reviews)
Stunning setting and views, beautiful accommodation, amazing breakfast, and our host Dot can’t do enough to please. Best B&B I have ever stayed at!
Reviewed on 5 Dec, 2025
Bristol Grand Hotel By Sunday
Bristol City Centre
Price was US$ 1,001, price is now US$ 926 per person
US$ 926
per person
Apr 10 - Apr 13
found 23 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Bristol (BRS)
7.8/10 Good! (1,000 reviews)
The room was cold (I didn’t realise you had to turn the heating on). There was very heavy rain and the noise on a flat roof outside our window was unbearable. We changed rooms at midnight. The following night a Turkish wedding with drums until midnight. Shower great. Beds comfortable. Towels have seen better days. Receptionist very helpful
Reviewed on 28 Jan, 2026
Clayton Hotel Bristol City
Bristol City Centre
Price was US$ 1,037, price is now US$ 976 per person
US$ 976
per person
Apr 10 - Apr 13
found 23 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Bristol (BRS)
9.2/10 Wonderful! (1,095 reviews)
Very polite, efficient and friendly staff.
The king size executive room we booked was brilliant, very spacious, clean and extremely comfy bed.
We booked several months in advance so the price was pretty reasonable. Usually we need a hotel a short notice and this hotel is out of our price range.
The 2 course dinner was very good value for money with generous portions.
Reviewed on 31 Jan, 2026
Find the Best Chepstow Vacation Packages
Chepstow Essential Information
Language | Welsh |
|---|---|
Currency | British pounds sterling |
Population | 16,200 |
Max Temp Winter | 45ºF |
Max Temp Summer | 65ºF |
Top Sights | Chepstow Castle, Chepstow Castle and Caldicot Castle |
Chepstow Hotel Deals
Delta Hotels by Marriott St. Pierre Country Club
St Pierre Park Chepstow Wales
Fully refundableReserve now, pay when you stay
8.2/10 Very Good! (1,009 reviews)
Great service and room
Reviewed on 27 Jan, 2026
Two Rivers, Chepstow by Marston’s Inns
Newport Road Chepstow Wales
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (401 reviews)
Stay here a lot for work. Rooms are cozy, clean and modern. Beds super comfortable with plenty of pillows. Staff are really friendly.
Reviewed on 23 Jan, 2026
Clayton Hotel Bristol City
Broad Street Bristol England
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (1,196 reviews)
Room was very spacious, clean and well appointed. Will definitely stay here again.
Reviewed on 26 Jan, 2026
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.
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 lively bars and acclaimed theater scene in this relaxing area.
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.
What to do in Chepstow
Cardiff: South Wales Cliffs, Bays & Castles Day Tour
US$ 112
per adult
Cardiff: Gower Peninsula's Cliffs Scenic Day Tour
US$ 112
per adult
Cardiff: Waterfalls, Mountains & Castles Day Tour
US$ 118
per adult
100% of travellers recommend
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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.