The ruins of a large, historic stone building with multiple arches and a tall, narrow tower.

Chepstow Holidays from £148

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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.

Where to stay in Chepstow

Find the best Chepstow areas for the activities you enjoy most. Learn more about Chepstow
Learn more about Chepstow

Caerwent

Caerwent is noteworthy for its bars, and you can make a stop at top attractions like Caerwent Roman Town and Dewstow Golf Club.

Discover the most popular places to visit in Chepstow

What to do in Chepstow

Chepstow Hotel Deals

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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.

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.

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.

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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.