Chepstow Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 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

    Plan, book, and manage your trip all in one place

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 S$167 per night from 13 Nov to 14 Nov
S$167
13 Nov - 14 Nov
includes taxes & fees
8.2/10 Very good! (1,004 reviews)
"We recently stayed at Delta Hotels by Marriott St. Pierre Country Club and had a mixed experience overall. The location was lovely, and we particularly enjoyed the swimming pool and hot tub. Breakfast was also a highlight and a great way to start the day. The staff were excellent throughout our stay, ..."

Reviewed on 26 Oct, 2026

Delta Hotels by Marriott St. Pierre Country Club
Clayton Hotel Bristol City

Clayton Hotel Bristol City

4 out of 5
Broad Street Bristol England
Fully refundableReserve now, pay when you stay
The price is S$125 per night from 29 Nov to 30 Nov
S$125
29 Nov - 30 Nov
includes taxes & fees
9.2/10 Wonderful! (1,531 reviews)
"Highly impressive hotel - large spacious rooms, very clean and modern bathrooms. Stand out was the selection for breakfast. Well catered for all dietary restrictions etc."

Reviewed on 29 Oct, 2026

Clayton Hotel Bristol City
Celtic Manor Resort

Celtic Manor Resort

5 out of 5
Chepstow Road Newport Wales
Fully refundableReserve now, pay when you stay
The price is S$224 per night from 22 Nov to 23 Nov
S$224
22 Nov - 23 Nov
includes taxes & fees
8.6/10 Excellent! (1,439 reviews)
"Great place but very disappointed with the extortionate car parking charges!"

Reviewed on 28 Oct, 2026

Celtic Manor Resort
See all 3,826 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.

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

What to do in Chepstow

From Barry Island: Gavin and Stacey Tour

From Barry Island: Gavin and Stacey Tour

S$77
per adult
From Barry Island: Gavin and Stacey Tour
Caerphilly Castle

The Valleys tour or Swansea Bay tour. Please choose correctly.

S$125
per adult
100% of travellers recommend
The Valleys tour or Swansea Bay tour. Please choose correctly.
Cardiff: South Wales Cliffs, Beaches & Castles Day Tour

Cardiff: South Wales Cliffs, Beaches & Castles Day Tour

S$145
per adult
Cardiff: South Wales Cliffs, Beaches & Castles Day Tour
See all activities in Chepstow

Frequently asked questions

How much does a Chepstow holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday to Chepstow costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Chepstow?
Plan your getaway for the shoulder or low season and you're likely to score cheap Chepstow holiday packages. Remember that public holidays and major festivals and events can have an impact on prices, so do your research before you go.
How many days is enough for Chepstow?
Chepstow holidays can be as short or long as you like, but to really sink your teeth into this destination, we'd suggest 2 days is about right. This will mean you can fit in top attractions like Chepstow Museum and Parva Farm Vineyard and track down some lesser-known gems. Don't skip cool neighbourhoods such as Portskewett and Devauden either. If you're clever with your time, you can even take a day trip or two from Chepstow too.
Is it worth booking a holiday package to Chepstow?
Well known for its history and home to popular attractions like Chepstow Castle, a Chepstow holiday is sure to leave an impression. Another top sight worth exploring? Don't miss Symonds Yat Rock.
How to find the best Chepstow package deals?
Use Expedia's filters to help you find some unbeatable Chepstow package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Chepstow package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your holiday package as soon as possible.
Is it cheaper to book a Chepstow holiday as a package?
You can enjoy significant savings on your Chepstow escape by booking a customised holiday package. Click on the "Package" heading, then enter your travel dates and destination to browse the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to Chepstow?
If you're considering a spontaneous Chepstow getaway, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Chepstow?

  1. Choose when to travel: Check your calendar and get your bags packed. Your preferred time of year and the available activities will also help you decide when to escape to Chepstow.
  2. Plan your budget wisely: In addition to the price of your accommodation, you should consider other expenses. These include food, transportation and flights. Also, set aside some extra funds for unexpected costs that may arise during your trip to Chepstow.
  3. Decide how many days away: Start by listing all the activities and attractions you want to get to in Chepstow. Then, estimate how long you'll need at each, including any travel time.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to choose a Chepstow holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.