Chepstow Holidays from £297

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Your Chepstow Holiday

The easiest way to experience this interesting city is with a tailor-made Chepstow holiday package. Stay in the neighbourhood of Trellech United, which is good for culture, nature and history or go someplace else — our package deals are all about you. Fill your itinerary with visits to Chepstow Racecourse, Tintern Abbey and Chepstow Castle, some of the top attractions you simply have to see during a trip to Chepstow. Don't delay visiting this destination any longer. The ultimate Chepstow holiday is a few clicks away with Expedia.

The Latest Chepstow Holiday Deals

The Full Moon Inn

The Full Moon Inn

5 out of 5
per person
3 Jun - 6 Jun
Return flight included
Glasgow (GLA) to Bristol (BRS)
9.6/10 Exceptional! (42 reviews)
Property is well maintained. Lovely decor. Outside area is great. Rooms cosy and homely. Hot Water bottles a lovely touch. Fresh orange. Water and fresh milk in the mini fridge. Food is excellent. Lovely area to eat in and breakfast was hot and tasty. Would go again and hve been back 3 or 4 times already. Great place.

Reviewed on 12 Apr 2024

Mollie's Motel & Diner

Mollie's Motel & Diner

3.5 out of 5
per person
3 Jun - 6 Jun
Return flight included
Glasgow (GLA) to Bristol (BRS)
9.4/10 Exceptional! (1,724 reviews)
Get value, clean, quiet. Does the job well.

Reviewed on 23 Apr 2024

Lucknam Park Hotel & Spa

Lucknam Park Hotel & Spa

5 out of 5
Save 100% on your flight
per person
3 Jun - 6 Jun
Return flight included
Glasgow (GLA) to Bristol (BRS)
9.4/10 Exceptional! (129 reviews)
A stunning hotel in a beautiful setting. The staff are very helpful and friendly and so very welcoming. You truly felt like a VIP. Spa was wonderful. Breakfast was served by fabulous waiting staff and the food was spot on. Delicious and just the right amount. Easy on site parking and we especially appreciated the ev charging facility. There were 3 available. The garden is stunning. The only thing I would mention is that we booked a set price via Expedia for B&B, and dinner but when we checked out, we noticed a service charge had been added to our “ room rate” . We were more than happy to pay for service at the restaurant for dinner, but we were a bit surprised by that additional charge. It was not made clear on Expedia when we booked. However, we did manage to get the room service charge reduced, as the reception staff advised us that it was an “ optional charge” that was added to the bill. Good job we noticed it!

Reviewed on 21 Apr 2024

Whatley Manor

Whatley Manor

5 out of 5
per person
3 Jun - 6 Jun
Return flight included
Glasgow (GLA) to Bristol (BRS)
9.6/10 Exceptional! (49 reviews)
Staff here are beyond amazing! Special shout out to Alivia in the Spa. One of the best therapists across the world! Fantastic spa facilities. The most beautiful gardens. Responded well to feedback and went above and beyond in their customer service.

Reviewed on 10 Apr 2024

The Old Bell Hotel

The Old Bell Hotel

4 out of 5
per person
3 Jun - 6 Jun
Return flight included
Glasgow (GLA) to Bristol (BRS)
9.4/10 Exceptional! (217 reviews)
Exceptional staff,very helpful, rooms very clean and beautifully presented

Reviewed on 8 Mar 2024

Clayton Hotel Bristol City

Clayton Hotel Bristol City

4 out of 5
Bristol City Centre
per person
3 Jun - 6 Jun
Return flight included
Glasgow (GLA) to Bristol (BRS)
9/10 Wonderful! (481 reviews)
Great location, spacious rooms. Attractive interiors

Reviewed on 22 Apr 2024

Prices and availability subject to change. Additional terms may apply.

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

Our pick of the best Chepstow Hotel Deals

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
Stay at this 4-star golf hotel in Chepstow. Enjoy free WiFi, free parking and a golf course. Our guests praise the breakfast and the restaurant in their reviews. ...
8.2/10 Very Good! (983 reviews)
Lake view accommodation
"Generally clean and tidy although some splashes of coffee on the kettle which needed a clean and a couple of flaky marks on the soft chair but nothing too concerning. Nicely furnished and a good lake view with plenty of bird watching opportunities. Service from reception is excellent and the breakfast ..."

Reviewed on 21 Apr 2024

Delta Hotels by Marriott St. Pierre Country Club
Mollie's Motel & Diner
Mollie's Motel & Diner
3.5 out of 5
Cribbs Causeway, A4018, Bristol, England
Stay at this 3.5-star eco-certified hotel in Bristol. Enjoy free WiFi, free parking and breakfast. Our guests praise the breakfast and the helpful staff in their ...
9.2/10 Wonderful! (1,758 reviews)
"Everything was fine . Lady work over night is friendly . Thank you guys z"

Reviewed on 21 Apr 2024

Mollie's Motel & Diner
The Bristol Hotel
The Bristol Hotel
4 out of 5
Prince Street, Bristol, England
Stay at this business-friendly hotel in Bristol. Enjoy free WiFi, 2 bars/lounges and 2 coffee shops/cafes. Our guests praise the restaurant and the helpful staff ...
9/10 Wonderful! (1,004 reviews)
"From the time we arrived until we left it was perfect. Service was amazing & I would recommend having the breakfast. The food was good quality & plenty of choice. Wouldn’t hesitate to return , location is fantastic with the option of visiting the harbour or the city centre"

Reviewed on 20 Apr 2024

The Bristol Hotel
See all 3,234 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

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.

Discover the most popular places to visit in Chepstow

Image for Principality Stadium

Principality Stadium

4.5/5(198 reviews)

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
Image for Cardiff Bay

Cardiff Bay

4.5/5(190 reviews)

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

Cardiff Bay
Image for Cardiff Castle

Cardiff Castle

4.5/5(251 reviews)

Located in the heart of the city centre, Cardiff Castle is one of Wales’ most important cultural attractions. A rich history spanning 2,000 years is contained within its walls and fairytale-style towers.

Cardiff Castle

Unmissable things to do in Chepstow

Image for Private Day Tour of Cardiff, including Cardiff Castle, St Fagans, & Cardiff Bay

Private Day Tour of Cardiff, including Cardiff Castle, St Fagans, & Cardiff Bay

£640
Per adult
Private Day Tour of Cardiff, including Cardiff Castle, St Fagans, & Cardiff Bay
Image for Private Doctor Who Day Tour of South Wales - Castles, Cardiff, and Doctor Who!

Private Doctor Who Day Tour of South Wales - Castles, Cardiff, and Doctor Who!

£700
Per adult
Private Doctor Who Day Tour of South Wales - Castles, Cardiff, and Doctor Who!
Image for Cardiff: Doctor Who Walking Tour

Cardiff: Doctor Who Walking Tour

£145
Per adult
Cardiff: Doctor Who Walking Tour
See all activities in Chepstow

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.

* 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.