Chepstow Holidays from £154

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 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, 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.
OYO The Lodge Bournemouth

OYO The Lodge Bournemouth

Bournemouth City Centre
£154
per person
1 Oct - 4 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Bristol (BRS)
7/10 Good! (19 reviews)
No fan or ar conditioner in the room during this heat? Unbelievable! Worst night !

Reviewed on 15 Jul 2026

Langtry Manor Hotel

Langtry Manor Hotel

Save 100% on your flight
£233
per person
1 Oct - 4 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Bristol (BRS)
8.6/10 Excellent! (401 reviews)
Bathroom disgustingly dirty, door of shower hanging off, toilet when flushed water rose to the top so blocked, taps on bath not secure, many other items not working or partly working. Wouldn’t stay here again

Reviewed on 8 Aug 2026

Bournemouth West Cliff Hotel & Spa

Bournemouth West Cliff Hotel & Spa

Bournemouth City Centre
Save 100% on your flight
£255
per person
10 Sept - 13 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to Bristol (BRS)
8/10 Very good! (1,005 reviews)
Stayed in the superior family room. Whilst the main double bed was very comfortable. The 2 small single pull out beds her diabolical. Both children don’t sleep at all so all has to try and sleep in the main bed. Which was very tricky. The room was drab and outdated. The shampoo/shower gel bottles are very difficult to use. The toilet didn’t flush very well. No TV channels. You had to sign into the apps using your own details. So remember to sign out again when you leave. The pool was much smaller than on the photos. The pool was very nice and warm tho. The outside veranda was lovely. The music playing was very sad and emotional. The food was okay. Nothing to write home about. But nice. Breakfast was lovely. Loved the pancake machine. There are lots of people using the Spa facilities so playing in the pool can be awkward at times. Overall. It’s an okay stay. I would stay again. But in a better room

Reviewed on 8 Aug 2026

The Green House

The Green House

Bournemouth City Centre
Save 100% on your flight
£208
per person
1 Oct - 4 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Bristol (BRS)
9.2/10 Wonderful! (1,007 reviews)
Bamboo Guesthouse

Bamboo Guesthouse

Bournemouth City Centre
£196
per person
1 Oct - 4 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Bristol (BRS)
9.2/10 Wonderful! (131 reviews)
Self contained excellent place

Reviewed on 29 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

St Pierre Park Chepstow Wales
Fully refundableReserve now, pay when you stay
£93
31 Aug - 1 Sept
includes taxes & fees
8.2/10 Very good! (1,005 reviews)
"Very nice stay to recommend. Quiet rooms , helpful staff ,very good breakfast .Excellent Restaurant."

Reviewed on 8 Aug 2026

Delta Hotels by Marriott St. Pierre Country Club
Celtic Manor Resort

Celtic Manor Resort

Chepstow Road Newport Wales
Fully refundableReserve now, pay when you stay
£117
1 Sept - 2 Sept
includes taxes & fees
Celtic Manor Resort
Clayton Hotel Bristol City

Clayton Hotel Bristol City

Broad Street Bristol England
Fully refundableReserve now, pay when you stay
£87
16 Aug - 17 Aug
includes taxes & fees
9.2/10 Wonderful! (1,435 reviews)
"When we checked into our room it absolutely stank of cigarettes so we assumed the guest prior to us had been smoking in the room as particularly the bathroom was bad! Before popping down we opened a window and left our room to go out to dinner, upon return the smell was still just as bad so popped ..."

Reviewed on 8 Aug 2026

Clayton Hotel Bristol City
See all 3,828 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.

All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays
Golf Holidays
Golf Holidays
Luxury Holidays
Luxury Holidays
gay friendly holidays
LGBTQ+ Holidays
LGBTQ+ Holidays
Romantic Holidays
Romantic Holidays
Ski Holidays
Ski Holidays
Pet Friendly Holidays
Pet Friendly Holidays
Holiday in Month
Where to go when
Where to go when

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
A historic stone building on a cliff overlooking a beach.
Photo by Miguel Vasquez

Chepstow Castle

9.0/10 (29 reviews)
Chepstow Castle is the oldest surviving stone fort in Britain and easily one of the most spectacular castles in Wales. The impressive castle dates back to the Norman invasion and perches precariously atop a cliff on the banks of the River Wye. Any visit is sure to invoke plenty of awe and wonder.
See properties

Chepstow Racecourse

9.0/10 (26 reviews)
Chepstow Racecourse is situated in Monmouthshire in south-east Wales, near the southern end of the Wye Valley. The track is a great point of interest in the UK and attracts visitors from all over the world.
See properties

St. Pierre Country Club

7.6/10 (17 reviews)
Enjoy a round of golf in Mathern at St. Pierre Country Club. Visit the shops and top-notch restaurants in this walkable area.
See properties

Symonds Yat Rock

9.6/10 (7 reviews)
Commune with nature and explore the great outdoors at Symonds Yat Rock during your travels in Tidenham. Make time for the spas and golf courses in this relaxing area.
See properties

Gate House

10.0/10 (4 reviews)
You can learn about the history of Chepstow with a stop at Gate House. Visit the spas and top-notch restaurants in this walkable area.
See properties

Offa's Dyke National Trail - Southern Terminus

9.0/10 (7 reviews)
You can take time to visit Offa's Dyke National Trail - Southern Terminus during your travels to Tidenham.
See properties

Parva Farm Vineyard

10.0/10 (2 reviews)
You can enjoy a tasting or tour at Parva Farm Vineyard during your travels to Tintern. Visit the spas and cosy cafes in this family-friendly area.
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
Cardiff Bay Boat Tour

Cardiff Bay Boat Tour

£16
per adult
76% of travellers recommend
Cardiff Bay Boat Tour
Cardiff: Gower Peninsula's Cliffs Scenic Day Tour

Cardiff: Gower Peninsula's Cliffs & Mumbles Scenic Day Tour

£85
per adult
Cardiff: Gower Peninsula's Cliffs & Mumbles Scenic Day 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.