Title: Chepstow Holidays 2026 from £251 | Expedia.co.uk [Chepstow Travel Guide](https://expedia.co.uk/Chepstow.dx5618)[Hotels in Chepstow](https://expedia.co.uk/Chepstow-Hotels.d5618.Travel-Guide-Hotels)[Holiday Rentals in Chepstow](https://expedia.co.uk/Chepstow-Holiday-Rentals.d5618.Travel-Guide-HolidayRentals)[Flights to Chepstow](https://expedia.co.uk/Cheap-Flights-To-Chepstow.d5618.Travel-Guide-Flights)[Things to do in Chepstow](https://expedia.co.uk/Things-To-Do-In-Chepstow.d5618.Travel-Guide-Activities)[Chepstow Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Chepstow.d5618.Car-Hire-Guide) ![](https://images.trvl-media.com/place/6086409/fb8b13ac-189c-4b6e-a910-25ac56c540ec.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chepstow Holidays from £251 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to £335 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Packages with flights are ATOL protected #### Your Chepstow Holiday When a city break is calling, answer it with a holiday package to Chepstow. The neighbourhood 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](https://www.expedia.co.uk/Chepstow-Racecourse-Cardiff.d6171652.Attraction), [Tintern Abbey](https://www.expedia.co.uk/Tintern-Abbey-Cardiff.d6086409.Attraction) and [Chepstow Castle](https://www.expedia.co.uk/Chepstow-Castle-Cardiff.d6086505.Attraction). Expedia has what you need to escape your routine. Tailor your holiday to Chepstow to match your travel style, whatever that may look like. ## Top Chepstow Flight + Hotel Deals Price found within the past 48 hours. Click for updated prices. ![Bristol Grand Hotel By Sunday](https://images.trvl-media.com/lodging/1000000/450000/441100/441054/cb1a54c8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Bristol Grand Hotel By Sunday Bristol City Centre Save 100% on your flight £251 per person 30 Jan - 2 Feb found 1 day ago Return flight included Manchester (MAN) to Bristol (BRS) 7.8/10 Good! (1,000 reviews) The room was very spacious and clean. The lobby and bar staff were friendly and helpful. The car park however was very narrow and tight and leaving proved quite difficult with the exit tickets not working at machine. Reviewed on 22 Dec 2025 ## Chepstow Essential Information | Language | Welsh | | --------------- | -------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | British pounds sterling | | Closest Airport | Bristol Intl. Airport (BRS) | | Population | 16,200 | | Max Temp Winter | 7ºC | | Max Temp Summer | 18ºC | | Top Sights | [Berkeley Castle](https://www.expedia.co.uk/Berkeley-Castle-Berkeley.d6094215.Attraction), [Chepstow Castle](https://www.expedia.co.uk/Chepstow-Castle-Cardiff.d6086505.Attraction) and [Caldicot Castle](https://www.expedia.co.uk/Caldicot-Castle-Caldicot.d553248621532491483.Attraction) | ## Top hotels in Chepstow ![Delta Hotels by Marriott St. Pierre Country Club](https://images.trvl-media.com/lodging/1000000/70000/65900/65879/280a23d2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Delta Hotels by Marriott St. Pierre Country Club St Pierre Park Chepstow Wales Fully refundableReserve now, pay when you stay £79 2 Jan - 3 Jan 2026 includes taxes & fees 8.2/10 Very Good! (1,000 reviews) Very friendly staff and the hotel was very christmassy Reviewed on 7 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=02%2F01%2F2026&endDate=03%2F01%2F2026&selected=65879&PinnedHotelID=65879&HadPinnedHotel=true®ionId=5618) ![The Beaufort Hotel](https://images.trvl-media.com/lodging/1000000/890000/888400/888319/602343fe_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Beaufort Hotel Beaufort Square Chepstow Wales £63 24 Dec - 25 Dec includes taxes & fees 7.6/10 Good! (259 reviews) One issue was the en-suite.The toilet was too close to the radiator,which was on full temperature making it rather dangerous.Also felt excessive cost for charging EV vehicle.Having said that we were made very welcome,all staff very friendly,and helpful Reviewed on 3 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=24%2F12%2F2025&endDate=25%2F12%2F2025&selected=888319&PinnedHotelID=888319&HadPinnedHotel=true®ionId=5618) ![Clayton Hotel Bristol City](https://images.trvl-media.com/lodging/70000000/69830000/69825700/69825633/95670123_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Clayton Hotel Bristol City Broad Street Bristol England Fully refundableReserve now, pay when you stay £74 8 Jan - 9 Jan 2026 includes taxes & fees 9/10 Wonderful! (1,151 reviews) Lovely clean well presented hotel in a great location for theatres. Would definitely recommend Reviewed on 22 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=08%2F01%2F2026&endDate=09%2F01%2F2026&selected=69825633&PinnedHotelID=69825633&HadPinnedHotel=true®ionId=5618) [See all 3,315 properties in Chepstow](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=24%2F12%2F2025&endDate=25%2F12%2F2025®ionId=5618) 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. ### 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](https://www.expedia.co.uk/Chepstow-Hotels.d5618.Travel-Guide-Hotels). ### 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](https://www.expedia.co.uk/Chepstow-Hotels-Romantic-Hotel.0-0-d5618-tRomanticHotel.Travel-Guide-Filter-Hotels) 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](https://www.expedia.co.uk/Chepstow-Hotels-Family-Friendly-Hotel.0-0-d5618-tFamilyFriendlyHotel.Travel-Guide-Filter-Hotels) within our selection of hotels. You can also find a place to call home in one of the [holiday rentals in Chepstow](https://www.expedia.co.uk/Chepstow-Holiday-Rentals.d5618.Travel-Guide-HolidayRentals). With accommodation, activities, and adventure all waiting, there’s never been a better time to plan Chepstow family weekend breaks. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Holidays [](https://expedia.co.uk/lp/theme-holidays/all-inclusive-holidays?rfrr=editorial.All_Inclusive%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Holidays [](https://expedia.co.uk/lp/theme-holidays/beach-holidays?rfrr=editorial.Beach_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/kid-friendly-holidays?rfrr=editorial.Family_Friendly%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Holidays [](https://expedia.co.uk/lp/theme-holidays/golf-holidays?rfrr=editorial.Golf_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Holidays [](https://expedia.co.uk/lp/theme-holidays/luxury-holidays?rfrr=editorial.Luxury_Holidays.click) ![gay friendly holidays](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ+ Holidays [](https://expedia.co.uk/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ+_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Holidays [](https://expedia.co.uk/lp/theme-holidays/romantic-holidays?rfrr=editorial.Romantic_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Holidays [](https://expedia.co.uk/lp/theme-holidays/ski-holidays?rfrr=editorial.Ski_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/22/hero-image-pet-friendly_copy.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Pet Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/pet-friendly-holidays?rfrr=editorial.Pet_Friendly%20Holidays.click) ![Holiday in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.co.uk/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ### Popular places to visit ![Millennium Stadium featuring a river or creek and modern architecture](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/145000/145798-Millennium-Stadium.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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. [](https://expedia.co.uk/Principality-Stadium-Cardiff-City-Centre.d6084257.Attraction) ![Wales Millennium Centre showing modern architecture, a city and a square or plaza](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/145000/145664-Cardiff.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Cardiff Bay Explore the waterfront in Cardiff with a trip to Cardiff Bay. Discover the top-notch restaurants and acclaimed theatre scene in this relaxing area. [](https://expedia.co.uk/Cardiff-Bay-Butetown.d553248621532490507.Attraction) ![Cardiff Castle showing heritage architecture, château or palace and heritage elements](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/145000/145762-Cardiff-Castle.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Cardiff Castle Located in the heart of the city centre, Cardiff Castle is one of Wales’ most important cultural attractions. A rich history spanning 2,000 years is contained within its walls and fairytale-style towers. [](https://expedia.co.uk/Cardiff-Castle-Cardiff-City-Centre.d6084239.Attraction) ### What to do in Chepstow ![Cardiff Bay Boat Tour](https://mediaim.expedia.com/localexpert/734480/c26ff1e8-74f6-4a14-a3db-1e448a37f7cd.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Cardiff Bay Boat Tour £13 per adult **76%** of travellers recommend [](https://expedia.co.uk/things-to-do/cardiff-bay-boat-tour.a734480.activity-details) ![Cardiff: Alcotraz Immersive Prison Cocktail Experience](https://mediaim.expedia.com/localexpert/48840858/c02f0733-40e7-4890-bfc4-ac4e198a7b8b.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Cardiff: Alcotraz Immersive Prison Cocktail Experience £49 per adult [](https://expedia.co.uk/things-to-do/cardiff-alcotraz-immersive-prison-cocktail-experience.a48840858.activity-details) ![Cardiff: South Wales Cliffs, Beaches & Castles Day Tour](https://mediaim.expedia.com/localexpert/49610322/47544663-8046-4828-a0a8-586afaa2a63f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Cardiff: South Wales Cliffs, Bays & Castles Day Tour £88 per adult [](https://expedia.co.uk/things-to-do/cardiff-south-wales-cliffs.a49610322.activity-details) [See all activities in Chepstow](https://expedia.co.uk/things-to-do/search?rid=5618) ## Explore a world of travel with Expedia - 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