Chepstow Holidays

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Top hotels in Chepstow

The Chepstow Inn

The Chepstow Inn

3.5 out of 5
#2 Concession Road 6, Brockton, ON
The price is S$262 per night from 29 Aug to 30 Aug
S$262
29 Aug - 30 Aug
includes taxes & fees
9.6/10 Exceptional! (81 reviews)
"Kim and the Chepstow in were amazing. She greeted us with a friendly smile and gave us all the information we requested about the area around the Inn and interesting sites to visit. She prepared an amazing breakfast for us and had it ready at the time we asked. All around an amazing B&B and Kim made ..."

Reviewed on 19 Aug, 2025

The Chepstow Inn
SureStay Plus Hotel by Best Western Kincardine

SureStay Plus Hotel by Best Western Kincardine

2.5 out of 5
791 Durham Street, Kincardine, ON
Fully refundableReserve now, pay when you stay
The price is S$112 per night from 19 Sept to 20 Sept
S$112
19 Sept - 20 Sept
includes taxes & fees
8/10 Very Good! (980 reviews)
"Very kind staff, room was clean, functional and adequate. Good value for money."

Reviewed on 18 Aug, 2025

SureStay Plus Hotel by Best Western Kincardine
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
2 MILLENNIUM WAY, Kincardine, ON
7.8/10 Good! (252 reviews)
"Other than the pool the hotel was very clean. The staff was very friendly. The beds were comfortable. The manager was willing to open the breakfast area for us to play games in on the rainy day. The food at breakfast was not very warm."

Reviewed on 22 Aug, 2025

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Comfort Inn & Suites
See all 66 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?
You'll find cheap prices on Expedia for your Chepstow break. However, factors like the length of stay, hotel choice and season will determine how much your holiday to Chepstow costs.
What are the cheapest months to go to Chepstow?
The off-season is the best time to visit Chepstow if you're trying to keep costs down. Another tip for scoring cheap Chepstow holiday packages? Try to avoid public holidays and any major events.
How many days is enough for Chepstow?
With a well-organised travel plan, you can easily visit the top Chepstow attractions in a handful of days. But if you prefer to discover lesser-known spots or go on day tours, think about booking your Chepstow holiday for longer.
How to find the best Chepstow package deals?
Bagging a cheap Chepstow package deal is a cinch with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add a few filters and see what's available. You can fine-tune your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Chepstow package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Chepstow holiday as a package?
An Expedia holiday package could land you great savings when compared to arranging stays and flights separately. Better still, you can personalise your Chepstow escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a holiday package to Chepstow?
If you're planning a spur-of-the-moment Chepstow adventure, browse 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 score terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Chepstow?

  1. Choose your travel dates: What you'd like to do in Chepstow and your preferred season will help you decide when to go.
  2. Set your budget: Factor in costs such as flights, food and transportation when calculating how much to put aside for your trip to Chepstow. Then, choose a property that works with your budget, whether that's a wallet-friendly stay or a more luxurious getaway.
  3. Decide how many days away: Start by making a list of all the activities and attractions you'd like to experience in Chepstow. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a tailored Chepstow holiday package.

* 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.