Title: Chepstow Vacation Packages 2026 from $850 | Expedia.com [Chepstow Travel Guide](https://expedia.com/Chepstow.dx5618)[Hotels in Chepstow](https://expedia.com/Chepstow-Hotels.d5618.Travel-Guide-Hotels)[Vacation Rentals in Chepstow](https://expedia.com/Chepstow-Vacation-Rentals.d5618.Travel-Guide-VacationRentals)[Flights to Chepstow](https://expedia.com/Cheap-Flights-To-Chepstow.d5618.Travel-Guide-Flights)[Things to do in Chepstow](https://expedia.com/Things-To-Do-In-Chepstow.d5618.Travel-Guide-Activities)[Car Rentals in Chepstow](https://expedia.com/Car-Rentals-In-Chepstow.d5618.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6086409/fb8b13ac-189c-4b6e-a910-25ac56c540ec.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chepstow Vacations from $850 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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 Plan, book, and manage your trip all in one place ## 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](https://www.expedia.com/Chepstow-Racecourse-Cardiff.d6171652.Vacation-Attraction), [Tintern Abbey](https://www.expedia.com/Tintern-Abbey-Cardiff.d6086409.Vacation-Attraction) and [Chepstow Castle](https://www.expedia.com/Chepstow-Castle-Cardiff.d6086505.Vacation-Attraction). 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. ![The Snooty Fox](https://images.trvl-media.com/lodging/1000000/10000/3500/3423/00cbf85b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Snooty Fox $850 per person Apr 3 - Apr 7 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Bristol (BRS) 8.6/10 Excellent! (202 reviews) The Snooty Fox is a lovely pub/hotel offering a cordial and welcoming atmosphere. Our room was beautifully decorated with a very comfortable bed. We enjoyed an evening meal and a very nice breakfast. The staff are terrific and efficient. Our short stay was enjoyable and great value for money. We’ll go back anytime. Tetbury is delightful and walkable with many interesting individual shops. Reviewed on Nov 24, 2025 ![The Bull Hotel](https://images.trvl-media.com/lodging/58000000/57840000/57831900/57831847/345c0747_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Bull Hotel $894 per person Apr 3 - Apr 7 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Bristol (BRS) 9.2/10 Wonderful! (323 reviews) The room was spotless and the staff were very friendly and accommodating. My only criticism is that there was insufficient drawer space in the room for clothes, which is why the rating is four stars rather than five. Reviewed on Dec 27, 2025 ![Lords of the Manor Hotel](https://images.trvl-media.com/lodging/18000000/17770000/17766200/17766135/0a1a19c4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Lords of the Manor Hotel $1,450 per person Apr 3 - Apr 7 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Bristol (BRS) 9.8/10 Exceptional! (343 reviews) Faultless throughout! Reviewed on Jan 4, 2026 Don't see what you're looking for? See all available trips from Columbus to Chepstow [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-07/2026-03-14/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=BRS&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### Discover the most popular places to visit in Chepstow ![Millennium Stadium showing modern architecture and a river or creek](https://images.trvl-media.com/place/6084257/e0623f37-090c-417c-b9a3-3ceea290b34c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Principality Stadium 4/5(21 reviews) 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. [](https://expedia.com/Principality-Stadium-Cardiff-City-Centre.d6084257.Vacation-Attraction) ![Pierhead Building, a Grade One listed building of the National Assembly for Wales in Cardiff Bay, Wales. A Cardiff's landmark taken from Cardiff Bay.](https://images.trvl-media.com/place/553248621532490507/5dbf41fb-82e5-44f5-94c4-a1963ca618dd.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Cardiff Bay 4.5/5(26 reviews) Explore the waterfront in Cardiff with a trip to Cardiff Bay. Discover the lively bars and acclaimed theater scene in this relaxing area. [](https://expedia.com/Cardiff-Bay-Butetown.d553248621532490507.Vacation-Attraction) ![Cardiff Castle showing heritage elements, heritage architecture and a castle](https://images.trvl-media.com/place/6084239/ed41c62f-a193-4860-b2b1-e025766c3f02.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Cardiff Castle 4.5/5(93 reviews) A fortified tower from the 12th century, World War II tunnels and Welsh military history make a fascinating day out at this magnificent castle. [](https://expedia.com/Cardiff-Castle-Cardiff-City-Centre.d6084239.Vacation-Attraction) ### What to do in Chepstow ![Cardiff: South Wales Cliffs, Bays & Castles Day Tour](https://mediaim.expedia.com/localexpert/49610322/fc887d1b-1935-4547-8fbb-fa2e1453cb38.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Cardiff: South Wales Cliffs, Beaches & Castles Day Tour $120 per adult [](https://expedia.com/things-to-do/cardiff-south-wales-cliffs.a49610322.activity-details) ![Cardiff: Gower Peninsula's Cliffs Scenic Day Tour](https://mediaim.expedia.com/localexpert/49556120/2ed2191f-1f28-407b-b6ce-a614604a299d.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Cardiff: Gower Peninsula's Cliffs Scenic Day Tour $120 per adult [](https://expedia.com/things-to-do/cardiff-gower-peninsulas-cliffs-scenic-day-tour.a49556120.activity-details) ![From Cardiff: Guided Hike to 8 Waterfalls in Brecon Beacons](https://mediaim.expedia.com/localexpert/48015786/7d100141-82fd-4304-9999-849f37a4b3ad.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### From Cardiff: Guided Hike to 8 Waterfalls in Brecon Beacons $92 per adult [](https://expedia.com/things-to-do/from-cardiff-guided-hike-to-8-waterfalls-in-brecon-beacons.a48015786.activity-details) [See all activities in Chepstow](https://expedia.com/things-to-do/search?rid=5618) ## Chepstow Hotel Deals ![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 $89 nightly $107 total Feb 22 - Feb 23 Total with taxes and fees 8.2/10 Very Good! (1,002 reviews) Fab room, huge comfy bed, great food, and stunning views Reviewed on Feb 5, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F22%2F2026&endDate=2%2F23%2F2026&selected=65879&PinnedHotelID=65879&HadPinnedHotel=true®ionId=5618) ![Two Rivers, Chepstow by Marston’s Inns](https://images.trvl-media.com/lodging/32000000/31890000/31887100/31887058/bdb658ee_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Two Rivers, Chepstow by Marston’s Inns Newport Road Chepstow Wales Fully refundableReserve now, pay when you stay $60 nightly $72 total Feb 22 - Feb 23 Total with taxes and fees 9/10 Wonderful! (404 reviews) I have a great day rooms are clean and tidied and it’s a peaceful place to rest. Reviewed on Jan 31, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F22%2F2026&endDate=2%2F23%2F2026&selected=31887058&PinnedHotelID=31887058&HadPinnedHotel=true®ionId=5618) ![Delta Hotels by Marriott Bristol City Centre](https://images.trvl-media.com/lodging/1000000/10000/5000/4939/1b7bbd4f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Delta Hotels by Marriott Bristol City Centre 2 Lower Castle Street Bristol England Fully refundableReserve now, pay when you stay $72 nightly $87 total Mar 1 - Mar 2 Total with taxes and fees 8.6/10 Excellent! (558 reviews) Excellent hotel Reviewed on Feb 1, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F1%2F2026&endDate=3%2F2%2F2026&selected=4939&PinnedHotelID=4939&HadPinnedHotel=true®ionId=5618) [See all 3,280 properties in Chepstow](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F8%2F2026&endDate=2%2F9%2F2026®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. ## 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](https://www.expedia.com/Chepstow-Castle-Cardiff.d6086505.Vacation-Attraction), [Chepstow Castle](https://www.expedia.com/Chepstow-Castle-Cardiff.d553248621563222749.Vacation-Attraction) and [Caldicot Castle](https://www.expedia.com/Caldicot-Castle-Caldicot.d553248621532491483.Vacation-Attraction) | ## More vacations you might like 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[](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Chepstow vacation package cost? ### What are the cheapest months to go to Chepstow? ### How many days is enough for Chepstow? ### Is it worth booking a vacation package to Chepstow? ### How to find the best Chepstow package deals? ### Is it cheaper to book a Chepstow vacation as a package? ### When to book a vacation package to Chepstow? ### How to plan a trip to Chepstow? > 1. Choose when to go: Check your calendar and pack your bags. Your preferred time of year and the type of activities available will also help you decide when to escape to Chepstow. > 2. Calculate your budget: Make sure you have enough money to cover everything from dining out and transportation to flights and activities. Your accommodations will probably be the biggest expense during your trip to Chepstow. > 3. Use Expedia's [trip planning tool](https://www.expedia.com/why/trip-planning) to explore Chepstow: Research every aspect of your trip to Chepstow with this handy planner. Invite your friends and family to collaborate on a group getaway, search for hotels or things to do and make bookings. > 4. Decide how long to go for: Now that you're more familiar with Chepstow, you can work out the ideal length of your break. Pull together a draft plan and give yourself enough time to cover everything you want to do. > 5. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a tailored Chepstow vacation package. > 6. Book experiences or activities in advance: Whether it's entrance to a major attraction or a walking tour, you won't have to worry about missing out on the highlights of Chepstow. Find all the fun [things to do in Chepstow](https://www.expedia.com/Things-To-Do-In-Chepstow.d5618.Travel-Guide-Activities) with our dedicated travel guide. ### Does Expedia offer Book Now, Pay Later Chepstow vacation packages? \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - get up to 20% on select hotels when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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