Chepstow Vacation Packages

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Your Chepstow Vacation

When you book a Chepstow vacation package, you can kick back and enjoy your getaway to the fullest. Discover the highlights of this unique city knowing that all your travel needs have been taken care of before you go. Ready to sightsee? Spend some time exploring major attractions such as Walkerton Golf & Curling Club during your trip to Chepstow. Whatever your travel plans or budget, organizing a tailored Chepstow vacation is a cinch with Expedia.

Ready to book your vacation to Chepstow?

 

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Chepstow Hotel Deals

The Chepstow Inn

The Chepstow Inn

3.5 out of 5
#2 Concession Road 6, Brockton, ON
The price is CA $250 per night from Aug 21 to Aug 22
CA $250
CA $283 total
Aug 21 - Aug 22
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 Aug. 19, 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 CA $107 per night from Sep 7 to Sep 8
CA $107
CA $121 total
Sep 7 - Sep 8
includes taxes & fees
8/10 Very Good! (981 reviews)
"We did not enjoy the breakfast that was available. We had some trouble with the tv in the first room but the second room room we had no problems with operating the tv. Very helpful with any problems we had,, being prompt and most polite. The first room we preferred the bathroom there as to the later. ..."

Reviewed on Aug. 19, 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! (248 reviews)
"The room was pretty comfortable, lot of space, clean, the washroom as well. The breakfast was kind of disappointed, not variety, same things both mornings we stayed at the hotel"

Reviewed on Aug. 18, 2025

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Comfort Inn & Suites
See all 64 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.
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Discover the most popular places to visit in Chepstow

Walkerton Golf & Curling Club

Enjoy a round of golf in Walkerton at Walkerton Golf & Curling Club. Amble around the area's beaches or visit its casinos.

Walkerton Golf & Curling Club

Frequently asked questions

How much does a Chepstow vacation package cost?
You can grab a vacation package to this top destination on Expedia. However, how much your vacation to Chepstow costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Chepstow?
To pick up cheap Chepstow vacation packages, organize your getaway outside of peak times such as school holidays. You'll typically find lower prices and better availability when it's less busy.
How many days is enough for Chepstow?
With a well-planned schedule, you can easily visit the main Chepstow attractions in a few days. But if you want to discover lesser-known spots or take day trips, consider booking your Chepstow vacation for longer.
How to find the best Chepstow package deals?
Landing 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 maximum budget, apply a couple of filters and browse what's available. You can tweak your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to view the most affordable Chepstow package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Chepstow vacation as a package?
You can enjoy significant savings on your Chepstow retreat by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to see some great flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Chepstow?
If you have your Chepstow vacation dates locked in, book as early as you can to bag some awesome deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are perfect for travelling on a whim.
How to plan a trip to Chepstow?

  1. Choose the perfect time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to go to Chepstow.
  2. Figure out your budget: Ensure you have enough money to pay for everything from transportation and food to experiences and flights. Your hotel will likely be the biggest expense during your trip to Chepstow.
  3. Determine how many days away: Start by compiling a list of the activities and attractions you want to get to in Chepstow. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a personalized Chepstow vacation package.

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