Chepstow Vacations from $786

Book a Hotel + Flight or Car together to unlock savings

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.

The Latest Chepstow vacation packages

Price found within the past 48 hours. Click for updated prices.
SureStay Plus Hotel by Best Western Kincardine

SureStay Plus Hotel by Best Western Kincardine

2.5 out of 5
Price was $810, price is now $786 per person
$786
per person
Jan 29 - Feb 5
found 21 hours ago
Roundtrip non-stop flight included
San Antonio (SAT) to Kitchener (YKF)
8/10 Very Good! (1,001 reviews)
Front desk people were amazing

Reviewed on Dec 7, 2025

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Chepstow Hotel Deals

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
$71 nightly
The price is $80 total per night from Jan 3 to Jan 4
$80 total
Jan 3 - Jan 4, 2026
Total with taxes and fees
7.8/10 Good! (1,004 reviews)
Front desk people were amazing

Reviewed on Dec 7, 2025

SureStay Plus Hotel by Best Western Kincardine
Travellers Inn Hanover

Travellers Inn Hanover

2 out of 5
244 - 7th Avenue Hanover ON
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $81 total per night from Dec 14 to Dec 15
$81 total
Dec 14 - Dec 15
Total with taxes and fees
6.8/10 (569 reviews)
Room spotless + comfortable…all good, except a cap was left behind, our fault…a souvenir from Alaska. Please put it in a safe place awaiting our next visit. Thankyou SO much. Looking forward to our next visit…The Andersons

Reviewed on Dec 10, 2025

Travellers Inn Hanover
Best Western Plus Walkerton Hotel & Conference Centre

Best Western Plus Walkerton Hotel & Conference Centre

2.5 out of 5
10 East Ridge Road, Rural Route #2 Brockton ON
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $131 total per night from Jan 11 to Jan 12
$131 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
9.2/10 Wonderful! (661 reviews)
Great room. Fantastic breakfast. Always the best.

Reviewed on Dec 7, 2025

Best Western Plus Walkerton Hotel & Conference Centre
See all 56 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.

Find the Best Chepstow Vacation Packages

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 from $786 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.