Chepstow Holidays from £384

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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 Grand Hotel By Sunday
Bristol City Stays
Berwick Lodge
Bristol Marriott Royal Hotel
Rowan Tree Your Apartment

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 £79 per night from 9 Feb to 10 Feb
£79
9 Feb - 10 Feb
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
Value for money

Reviewed on 2 Feb 2026

Delta Hotels by Marriott St. Pierre Country Club
Two Rivers, Chepstow by Marston’s Inns

Two Rivers, Chepstow by Marston’s Inns

4 out of 5
Newport Road Chepstow Wales
Fully refundableReserve now, pay when you stay
The price is £53 per night from 22 Feb to 23 Feb
£53
22 Feb - 23 Feb
includes taxes & fees
9/10 Wonderful! (405 reviews)
Yes very clean

Reviewed on 2 Feb 2026

Two Rivers, Chepstow by Marston’s Inns
Delta Hotels by Marriott Bristol City Centre

Delta Hotels by Marriott Bristol City Centre

4 out of 5
2 Lower Castle Street Bristol England
Fully refundableReserve now, pay when you stay
The price is £64 per night from 22 Feb to 23 Feb
£64
22 Feb - 23 Feb
includes taxes & fees
8.6/10 Excellent! (560 reviews)
Excellent hotel

Reviewed on 1 Feb 2026

Delta Hotels by Marriott Bristol City Centre
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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* 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.