Chepstow Holidays

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    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$142 per night from 19 Jan to 20 Jan
S$142
includes taxes & fees
19 Jan - 20 Jan
8.2/10 Very Good! (1,003 reviews)
"Beautiful property"

Reviewed on 29 Dec,2024

Delta Hotels by Marriott St. Pierre Country Club
Celtic Manor Resort
Celtic Manor Resort
5 out of 5
Chepstow Road, Coldra Wood, Newport, Wales
The price is S$148 per night from 19 Jan to 20 Jan
S$148
includes taxes & fees
19 Jan - 20 Jan
8.2/10 Very Good! (1,204 reviews)
Nice hotel
"Nice hotel but patio doors were broke and could not access balcony"

Reviewed on 31 Dec,2024

Celtic Manor Resort
Mollie's Motel & Diner
Mollie's Motel & Diner
3.5 out of 5
Cribbs Causeway, A4018, Bristol, England
The price is S$137 per night from 16 Jan to 17 Jan
S$137
includes taxes & fees
16 Jan - 17 Jan
9.2/10 Wonderful! (2,003 reviews)
Fab place to stay
"This was a lovely place to stay. From the minute we walked in to the minute we checked out the staff were friendly and very helpful. The dinner was fantastic, i had the best eggs ever there, they were cooked to perfection"

Reviewed on 2 Jan,2025

Mollie's Motel & Diner
See all 3,058 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.

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.

Popular places to visit

Millennium Stadium showing a river or creek and modern architecture

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
Cardiff Castle featuring heritage architecture, heritage elements and château or palace

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
Barry Island Beach

Barry Island Beach

4/5(76 reviews)

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

Leather workshops, Private classes

Leather workshops, Private classes

S$323
per adult
Leather workshops, Private classes
From Cardiff: Guided Tour of Welsh Valleys

From Cardiff: Guided Tour of Welsh Valleys

S$150
per adult
100% of travellers recommend
From Cardiff: Guided Tour of Welsh Valleys
Alcotraz Prison Cocktail Experience in Cardiff

Alcotraz Prison Cocktail Experience in Cardiff

S$80
per adult
Alcotraz Prison Cocktail Experience in Cardiff
See all activities in Chepstow

* 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.