Chepstow Holidays from £219

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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.
Charles Hope Apartments Swindon

Charles Hope Apartments Swindon

3.5 out of 5
Save 100% on your flight
per person
9 Sept - 13 Sept
found 1 day ago
Return flight included
Glasgow (GLA) to Bristol (BRS)
7.2/10 Good! (12 reviews)
Brilliant, I did leave a review on Google maps also. But I really enjoyed this stay. Me (m19) and my partner (F18) decided to go on a whim and book somewhere nice on Saturday night. It was a nice idea as we got out of her parents house. We really enjoyed our stay, the apartment was clean with a nice bathroom, kitchen, living area and bedroom. We cooked ourselves a meal and had a nice bath before heading out. It's literally on the doorstep of town so everything you need is within walking distance and there's also a washing machine and drying racks along with ironing boards and all that. I would definitely stay again. Only issue was parking as it's quite expensive. But there's a small parking lot opposite side of the street for £10 for 24 hours which is what I used. I definitely recommend. Check in was also really easy door codes worked with zero issues.

Reviewed on 18 May 2025

Redmayne House

Redmayne House

3.5 out of 5
Clifton
Save 100% on your flight
per person
19 Sept - 26 Sept
found 1 hour ago
Return direct flight included
Bristol (BRS) to Bristol (BRS)
9.2/10 Wonderful! (15 reviews)
Beautiful, well furnished apartment. Spotlessly clean. Well stocked kitchen. Loved the L'Occitane toiletries in bathroom. Very luxe! Great to have Nespresso Machine with pods too. So many great dining options nearby. Cool to hear students practising in the Uni Music School Building opposite the apartment.

Reviewed on 30 Apr 2025

Alison Court

Alison Court

3 out of 5
Clifton
per person
19 Sept - 26 Sept
found 1 hour ago
Return direct flight included
Bristol (BRS) to Bristol (BRS)
8.4/10 Very Good! (56 reviews)
The check in Apt and virtual key were unusual for me but the instructions were clear and easy to follow. The apartment was pristine and very inviting. I would recommend Alison Court to friends and family. I hope that on my next visit I am able to book for a longer stay.

Reviewed on 13 Oct 2023

Beech House

Beech House

4 out of 5
per person
19 Sept - 26 Sept
found 1 hour ago
Return direct flight included
Bristol (BRS) to Bristol (BRS)
9.4/10 Exceptional! (164 reviews)
I would stay there again. However it would have been nice to have instructions on how to use the appliances. Had to figure out using chatgbt how to use dishwasher and washer/dryer. Could have had more kitchen garbage bags. There was just the one there and no others.

Reviewed on 16 May 2025

Berwick Lodge

Berwick Lodge

5 out of 5
Hallen
Save 100% on your flight
per person
22 Sept - 25 Sept
found 21 hours ago
Return flight included
Edinburgh (EDI) to Bristol (BRS)
9.2/10 Wonderful! (154 reviews)
The hotel and the grounds were full of character. The bathroom was incredible. However, the issue was the noise. Needs some serious sound proofing. The room was above reception and was incredibly noisy. Also, the room lacked services considering the price per night. Limited drinks available, and had to ask for bathrobes.

Reviewed on 13 Mar 2025

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
The price is £84 per night from 31 Aug to 1 Sept
£84
31 Aug - 1 Sept
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"Beautiful buildings and setting when you first arrive driving through the golf course. I had previously asked for an early check in as we were attending a wedding off site, however they did not manage that for us, so we stored our bags and checked in on our return from the wedding. Breakfast was ..."

Reviewed on 1 Aug 2025

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

Celtic Manor Resort

5 out of 5
Chepstow Road, Coldra Wood, Newport, Wales
Fully refundableReserve now, pay when you stay
The price is £107 per night from 12 Aug to 13 Aug
£107
12 Aug - 13 Aug
includes taxes & fees
8.2/10 Very Good! (1,293 reviews)
"This is a gem of a place! Thoroughly enjoyed the stay and the experience. Great staff who are welcoming! Definitely coming back again!"

Reviewed on 27 Jul 2025

Celtic Manor Resort
Hotel Indigo Cardiff by IHG

Hotel Indigo Cardiff by IHG

4 out of 5
Dominions Arcade Queen Street, Glamorgan, Cardiff, Wales
Fully refundable
The price is £80 per night from 1 Sept to 2 Sept
£80
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (1,423 reviews)
"Very large room with beautiful modern bathroom. Beautifully curated design. Walking distance to everything in Cardiff. 10/10!"

Reviewed on 1 Aug 2025

Hotel Indigo Cardiff by IHG
See all 3,172 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

Popular places to visit

Millennium Stadium featuring a river or creek and modern architecture

Principality Stadium

The spiritual home of Welsh rugby, the Principality Stadiumin Cardiff is one of the most famous sporting arenas on the planet, envied the world over for its cauldron-like atmosphere and state-of-the-art facilities.

Principality Stadium
Wales Millennium Centre showing modern architecture, a city and a square or plaza

Cardiff Bay

Explore the waterfront in Cardiff with a trip to Cardiff Bay. Discover the lively bars and acclaimed theatre scene in this walkable area.

Cardiff Bay
Barry Island Beach

Barry Island Beach

If you’re looking for a quintessential Welsh seaside experience, look no further than Barry Beach in the picturesque Vale of Glamorgan.

Barry Island Beach

What to do in Chepstow

A tour arrives at Caerleon.

The Wandering Bard's Valley Tour or the Swansea Bay Tour.

£90
per adult
The Wandering Bard's Valley Tour or the Swansea Bay Tour.
Cardiff Bay Boat Tour

Cardiff Bay Boat Tour

£13
per adult
74% of travellers recommend
Cardiff Bay Boat Tour
Cardiff: Doctor Who City Walking Tour

Cardiff: Doctor Who City Walking Tour

£17
per adult
Cardiff: Doctor Who City Walking 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.

* 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.