Chepstow Holidays

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Top hotels in Chepstow

The Barn at Spry Point

The Barn at Spry Point

2 out of 5
222 Ark Lane Lot B The Barn Little Pond PE
Fully refundableReserve now, pay when you stay
The price is €85 per night from 21 Jul to 22 Jul
€85
21 Jul - 22 Jul
includes taxes & fees
9/10 Wonderful! (79 reviews)
"The property is unique in that it appears to have retrofitted from a barn. Parking is on gravel and grass, and we were immediately greeted by swarms of mosquitoes as soon as we got off the car. The mosquitoes followed us all the way into our room, which led to an unpleasant start to our stay. The ..."

Reviewed on 13 Jul 2026

The Barn at Spry Point
Johnson Shore Inn

Johnson Shore Inn

3 out of 5
9984 Northside Road, Route 16 Rock Barra PE
The price is €164 per night from 3 Aug to 4 Aug
€164
3 Aug - 4 Aug
includes taxes & fees
9.8/10 Exceptional! (247 reviews)
"Beautiful room clean and well considered. Hosts are friendly and very helpful Look forward to staying again"

Reviewed on 13 Jul 2026

Johnson Shore Inn
Rollo Bay Inn

Rollo Bay Inn

2.5 out of 5
1067 Lower Rollo Bay Rd Rollo Bay PE
The price is €127 per night from 15 Jul to 16 Jul
€127
15 Jul - 16 Jul
includes taxes & fees
8.4/10 Very good! (17 reviews)
"Jay, the owner, really make you feel welcome and appreciated! The place is really cozy and charming! We really enjoyed our stay! Thanks for the amazing service! I recommend this place!"

Reviewed on 22 Jun 2026

Rollo Bay Inn
See all 120 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 great value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Chepstow costs! Expedia's packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Chepstow?
To pick up cheap Chepstow holiday packages, organise your getaway outside of peak times such as school holidays. You'll generally find lower prices and better availability in the off-season or when it's less busy.
How many days is enough for Chepstow?
With a well-planned schedule, you can easily visit the most popular Chepstow sights in a handful of days. But if you'd like to discover lesser-known spots or take day trips, consider booking your Chepstow holiday for longer.
How to find the best Chepstow package deals?
Finding a cheap Chepstow package deal is easy with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Chepstow package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Chepstow holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll generally get a better deal than booking each component separately. And you'll still get the freedom to create a tailored Chepstow holiday by choosing your preferred type of stay, airline and car class.
When to book a holiday package to Chepstow?
Enjoy incredible bargains by reserving your flights ahead of time with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Chepstow trip.
How to plan a trip to Chepstow?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to travel to Chepstow.
  2. Plan your budget wisely: Besides the price of your hotel, you should consider other expenses too. These include food, transportation and flights. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Chepstow.
  3. Decide your trip length: Consider how long you want to spend exploring Chepstow. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Combine your accommodation and airfare: After you've settled on your travel dates and duration, lock in the right Chepstow holiday package for you.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.