Chepstow Holidays from £257

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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, Tintern Abbey and Chepstow Castle. 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 City Stays

Bristol City Stays

3.5 out of 5
Saint Paul's
Price was £321, price is now £257 per person
£257
per person
4 Sept - 8 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to Bristol (BRS)
9/10 Wonderful! (52 reviews)
Super clean room, I received an unexpected upgrade and it really was superb. Kitchen very well fitted out with everything you might need. The location is excellent and the property manager amazing. Quick with replies and I didn’t feel like anything was too much trouble. The bed was so comfy and the pillows are the best I have ever slept on! The cleanliness throughout the property was fabulous. All in all a perfect 10/10 stay. Thank you

Reviewed on 24 Jun 2026

Meryan House Hotel

Meryan House Hotel

4 out of 5
Price was £760, price is now £597 per person
£597
per person
17 Aug - 24 Aug
found 1 day ago
Return flight included
Edinburgh (EDI) to Bristol (BRS)
8.8/10 Excellent! (54 reviews)
Quirky place, very old and it felt like it but for what i needed it was fine. Wifi was pretty bad.

Reviewed on 7 Jul 2026

Bristol Marriott Royal Hotel

Bristol Marriott Royal Hotel

4 out of 5
Bristol Floating Harbour
Save 100% on your flight
Price was £489, price is now £398 per person
£398
per person
4 Sept - 8 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to Bristol (BRS)
9/10 Wonderful! (1,308 reviews)
I enjoyed my stay … reception staff were amazing

Reviewed on 10 Jul 2026

YourApartment Cotham Arms

YourApartment Cotham Arms

4 out of 5
Price was £342, price is now £279 per person
£279
per person
4 Sept - 8 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to Bristol (BRS)
8.4/10 Very good! (12 reviews)
Upon arrival the room was relatively clean and straightened out nicely. Decorated to an OK standard. However, the room itself was absolutely sweltering and could've done with a fan or a portable air conditioning unit. I had to open both the windows wide to let some cool air in.....which unfortunately let the screaming and shouting from outside in too. But hey, I've booked something in the heart of student land so that's sort of on me as well! As far as cleanliness goes....look a little closer you'll see things aren't so great and definitely lacks attention to detail in that are. Not the worst but certainly not the best. It looks like shower gel, handwash and shampoo were provided once upon a time but now all that remain are empty containers. This is such a basic thing so either do it or don't. Kitchenette area was reasonably clean with utensils, plates bowls and a dishwasher provided. Overall, it was OK but could do better. It seems like somebody has lost interest in it!

Reviewed on 21 Sept 2025

De Vere Tortworth Court

De Vere Tortworth Court

4 out of 5
Price was £356, price is now £297 per person
£297
per person
4 Sept - 8 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to Bristol (BRS)
8.6/10 Excellent! (1,002 reviews)
A very enjoyable stayed one night for wedding reception will stay again.

Reviewed on 10 Jul 2026

Things to do near Chepstow

Chepstow, Wales, is perfect for outdoor enthusiasts and adventure seekers, offering stunning scenery and a range of activities. Visitors can enjoy golf at local courses, explore the area through personal and cultural tours, or embark on waymarked walks. With its captivating landscapes and rich heritage, Chepstow provides an ideal backdrop for a memorable holiday experience.

Shopping

Chepstow offers a charming shopping experience with local boutiques and gift shops. If you’re up for a drive, consider visiting the Cabot Circus Shopping Centre, Clifton Arcade, or Broadmead Shopping Centre, each 20.9km away, boasting a vibrant atmosphere with a mix of entertainment and family-friendly options.

Recreation

Experience the charm of Dewstow Gardens & Hidden Grottoes, only 8.0km from Chepstow, where you can unwind amidst beautiful landscapes and tranquil grottoes. For a cultural outing, visit the Bristol Hippodrome Theatre, 20.9km away, offering captivating performances in a romantic setting.

Adventure

Puzzlewood, located 16.1km from Chepstow, offers enchanting woodland paths and fascinating rock formations, perfect for exploration. For an adrenaline rush, visit Delta Force Paintball North Bristol, 12.9km away, where families can engage in thrilling paintball battles. Don't miss Perrygrove Railway & Treetop Adventure, also 16.1km out, featuring exhilarating treetop walks.

Nightlife

Chepstow offers a vibrant nightlife with a mix of cosy pubs and lively bars. Enjoy a pint at The Three Tuns for a traditional experience, or dance the night away at The Riverbank. The atmosphere is welcoming, perfect for both locals and visitors seeking a fun evening out.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Chepstow

Chepstow, Wales, is perfect for outdoor and adventure enthusiasts, boasting stunning scenery and a rich cultural experience. Key attractions include the impressive Chepstow Castle, the informative Chepstow Museum, and various urban parks. Whether you're seeking historical sites or vibrant city life, Chepstow offers a delightful mix of activities and sights, making it an ideal destination for tourists looking to explore the charm of this historic town.

  • Wye Valley: Explore the breathtaking Wye Valley, known for its stunning natural beauty and outdoor adventures. This picturesque valley, located 12.9km from Chepstow, offers activities like hiking, cycling, and river excursions, perfect for nature enthusiasts seeking a bit of excitement.
  • Tintern Abbey: Immerse yourself in history at the enchanting ruins of Tintern Abbey, situated within Chepstow. With its striking Gothic architecture and serene surroundings, this site provides a cultural experience that reflects the rich heritage of the region.
  • Chepstow Castle: Discover the romantic allure of Chepstow Castle, a magnificent fortress nestled in the heart of the town. With its impressive stone walls and rich history, it offers a captivating glimpse into medieval life and culture.

Best time to go to Chepstow

The best time to visit Chepstow is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly cloudy with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January40.6°F (4.8°C)Light RainMostly CloudyAverageSlightly Low
February41.5°F (5.3°C)Light RainMostly CloudyAverageSlightly Low
March43.9°F (6.6°C)Light RainMostly CloudyAverageSlightly Low
April47.8°F (8.8°C)Light RainMostly CloudySlightly HighAverage
May53.2°F (11.8°C)Light RainMostly CloudyAverageAverage
June58.6°F (14.8°C)Light RainMostly CloudyAverageSlightly High
July62.1°F (16.7°C)Light RainMostly CloudySlightly HighSlightly High
August61.2°F (16.2°C)Light RainMostly CloudySlightly HighAverage
September57.7°F (14.3°C)No RainMostly SunnyAverageSlightly High
October52.7°F (11.5°C)Light RainMostly CloudySlightly LowAverage
November46.4°F (8.0°C)Light RainMostly CloudySlightly LowAverage
December42.8°F (6.0°C)Light RainMostly CloudySlightly LowAverage

Tips to save on your trip to Chepstow

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Chepstow.
  • Consider traveling to Chepstow during the low season (January to March) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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, Chepstow Castle and Caldicot Castle

Top hotels in Chepstow

Delta Hotels by Marriott St. Pierre Country Club

Delta Hotels by Marriott St. Pierre Country Club

4 out of 5
St Pierre Park Chepstow Wales
Fully refundableReserve now, pay when you stay
The price is £93 per night from 10 Aug to 11 Aug
£93
10 Aug - 11 Aug
includes taxes & fees
8.2/10 Very good! (1,002 reviews)
"A lovely setting, it just looked tired in certain areas. It was unfortunate that we had a non-refundable rate and the hotel closed the golf course (the main reason for staying) because of the heat. The hotel would not agree to change the date, so the trip became a bit of a non event"

Reviewed on 1 Jul 2026

Delta Hotels by Marriott St. Pierre Country Club
Mollie's Bristol

Mollie's Bristol

4 out of 5
Cribbs Causeway Bristol England
The price is £70 per night from 2 Aug to 3 Aug
£70
2 Aug - 3 Aug
includes taxes & fees
9.4/10 Exceptional! (2,106 reviews)
"convenient parking right outside the your room"

Reviewed on 9 Jul 2026

Mollie's Bristol
Clayton Hotel Bristol City

Clayton Hotel Bristol City

4 out of 5
Broad Street Bristol England
Fully refundableReserve now, pay when you stay
The price is £108 per night from 19 Jul to 20 Jul
£108
19 Jul - 20 Jul
includes taxes & fees
9.2/10 Wonderful! (1,398 reviews)
"A good modern hotel well situated in the city centre. The room was pleasant and well furnished. My initial room allocation was ground floor with a dingy outlook but it was no problem to change. The breakfast was a good standard. The staff were friendly and helpful. Recommended!"

Reviewed on 10 Jul 2026

Clayton Hotel Bristol City
See all 3,687 properties in Chepstow
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.

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.

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Stay near popular Chepstow attractions

A historic stone cathedral with large arches and Gothic windows.

Tintern Abbey

9.6/10 (60 reviews)
The monastic ruins of Tintern Abbey are nestled in the heart of the Wye Valley area of outstanding natural beauty and can boast 900 years of history in their walls. This was the first Cistercian abbey built in Wales and only the second in Britain, and despite now being exposed to the elements, it remains one of the most stunning surviving examples of gothic architecture in the country.
See properties

What to do in Chepstow

From Barry Island: Gavin and Stacey Tour

From Barry Island: Gavin and Stacey Tour

£45
per adult
From Barry Island: Gavin and Stacey Tour
The Wandering Bard's Valley Tour or the Swansea Bay Tour.

The Valleys tour or Swansea Bay tour. Please choose correctly.

£86
per adult
100% of travellers recommend
The Valleys tour or Swansea Bay tour. Please choose correctly.
Cardiff Bay Boat Tour

Cardiff Bay Boat Tour

£16
per adult
76% of travellers recommend
Cardiff Bay Boat Tour
See all activities in Chepstow

Frequently asked questions

Why should I book my Chepstow holiday with Expedia?
Expedia has your back for all aspects of your Chepstow holiday. You'll always land the best deals, but when you bundle your accommodation, flights and/or hire car into a holiday package, you'll score even more savings. Looking to really make the most of your escape? Add some tours and activities to your package. We offer flexible cancellation policies on almost all bookings, so you won't need to worry if your plans change. Visit our Customer Service Portal link to discover more.
When is the best time of year to holiday in Chepstow?
To enjoy the buzz of peak season, pack your bags for January, February and July. August, November and December are typically quieter and a smart idea if you'd rather escape the crowds. To give you an idea of the type of weather you can experience, the average temperature during the day in January, the coolest month in Chepstow, is 4ºC. The warmest period here is July, when temperatures reach an average of 16ºC.
What are the top hotels for my holiday in Chepstow?
Delta Hotels by Marriott St. Pierre Country Club will make a perfect base for your Chepstow adventures. Located in Devauden, it's one of this area's most popular hotels.
How do I get a cheap holiday to Chepstow?
Combine your hotel and flight bookings, toss in extras such as activities, and save with a Chepstow holiday. You won't just land exciting discounts on your adventure — you'll have lots of choice at your fingertips too. When you book through Expedia, you can choose from more than 400 partner airlines and 321,000 properties throughout the world. Your next affordable holiday begins right here, right now! Learn more about how you can save money on your next holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Chepstow holiday?
Make sure your next holiday in Chepstow is one to remember by stopping by its top attractions. Chepstow Racecourse, Tintern Abbey, Chepstow Castle and Caldicot Castle are among the things to put on your itinerary while you're in the city.
What is the best area to stay in when on holiday in Chepstow?
There's so much to see in Chepstow, so stay close to its best attractions and treat yourself to more time sightseeing. Chepstow Racecourse is one place to put on your to-do list.
Do I need a visa for my Chepstow holiday?
Visa requirements for Chepstow vary based on your nationality and the purpose of your visit. We recommend checking official government websites to determine if you need a visa for your holiday. This is also a good place to find the most up-to-date information, including details about application procedures or any supporting documentation that may be necessary. Research your visa requirements well in advance to ensure a smooth travel experience. Also check to see that your passport is valid for at least six months from your date of return.
What should I wear on my Chepstow holiday?
Do a little research into the sorts of things people in Chepstow wear, and consider browsing style blogs for some fashion tips. You'll want to create a versatile travel wardrobe with pieces that suit your destination and showcase your personal style. Daytime temperatures in January, Chepstow's coolest month, are around 4ºC. July marks this city's warmest month when average temperatures reach 16ºC. Our tip? Take the guesswork out of what to pack and check the local weather forecast.
What does an Expedia Chepstow holiday include?
Expedia has everything you need to arrange your Chepstow trip, but how your package is structured is entirely up to you. Select from any combination of flights, hire cars and hotels. Searching for a few activities to keep you entertained? Once you've made your booking, you can add them on too. No matter your style or budget, there's a holiday package to suit your needs. Cottages and private holiday homes are two popular property types in Chepstow. Whatever your group size or holiday style, you can count on Expedia for the freedom to tailor your next escape.
Does Expedia offer Book Now, Pay Later Chepstow holidays?
Your bank balance shouldn't prevent you from escaping on holiday, so Expedia has come up with a solution to help. Now that we've partnered with online lender Klarna, it's easier than ever to book a dream getaway without draining your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your escape. Consider one of these flexible payment options:

  • Pay monthly holidays: Jet off on that dream holiday sooner with Klarna's manageable payment plans. If paying in multiple instalments sounds right for you, choose this option at checkout.
  • No-deposit holidays: Pressing the "book now" button is much easier with this option. With no deposit required for your holiday, you can Book Now, Pay Later and start packing your bags.

Can I choose my airline with a Chepstow Expedia holiday?
Expedia has access to more than 400 partner airlines globally, so you definitely can. Just choose your preferred air carrier and put together your ideal Chepstow getaway.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.