Chepstow Vacations

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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.

Chepstow Hotel Deals

The Chepstow Inn

The Chepstow Inn

3.5 out of 5
#2 Concession Road 6, Brockton, ON
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

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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
$70 nightly
The price is $79 total per night from Oct 19 to Oct 20
$79 total
Oct 19 - Oct 20
Total with taxes and fees
7.8/10 Good! (1,026 reviews)
"All was good"

Reviewed on Oct 12, 2025

SureStay Plus Hotel by Best Western Kincardine
TownePlace Suites by Marriott Kincardine

TownePlace Suites by Marriott Kincardine

3 out of 5
19 Millenium Way, Kincardine, ON
$115 nightly
The price is $130 total per night from Nov 8 to Nov 9
$130 total
Nov 8 - Nov 9
Total with taxes and fees
8.4/10 Very Good! (638 reviews)
"Top floor VERY HOT in hallways. Desk staff not present, door shut. someone waited for 10min to check in."

Reviewed on Oct 7, 2025

TownePlace Suites by Marriott Kincardine
See all 62 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.

Chepstow Essential Information

Language
English
Currency
Canadian dollars
Max Temp Winter
25ºF
Max Temp Summer
70ºF
Top Sights
Walkerton Golf & Curling Club, Whispering Hills Golf Club and Brant Tract Trails Trailhead

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Frequently asked questions

How much does a Chepstow vacation 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 vacation to Chepstow costs.
What are the cheapest months to go to Chepstow?
If you're hoping to book a cheap Chepstow vacation package, consider planning a trip in January, February and June. You're likely to find better rates on airfares and hotels during these quieter months — perfect for travelers wishing to save money.
How many days is enough for Chepstow?
With a well-organized itinerary, you can easily hit the main Chepstow sights in a few days. But if you prefer to discover lesser-known spots or go on day trips, consider booking your Chepstow vacation 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," "Traveler 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 traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Chepstow vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging stays and flights separately. Better still, you can personalize 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 vacation 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.
Does Expedia offer Book Now, Pay Later Chepstow vacation packages?
If you're like us, you love discovering new places but don't love the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the overall cost of your Chepstow break over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.