Chepstow Vacations from $1,016
Book a Hotel + Flight or Car together to unlock savings
Your Chepstow Vacation
The stress-free way to experience this lively city is with a custom-made Chepstow vacation package. Stay in the neighborhood of East Point, which is great for history, nature and watersports or choose someplace else — our packages are all about you. If seeing the sights is a priority during your trip to Chepstow, make sure you check out leading attractions like Basin Head Provincial Park and Basin Head Fisheries Museum. No matter your travel plans or budget, organizing your ultimate tailored Chepstow vacation is simple with Expedia.
The Latest Chepstow vacation packages
Price found within the past 48 hours. Click for updated prices.
The Hotel on Pownal
Downtown Charlottetown
$1,056
per person
Nov 1 - Nov 7
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Charlottetown Alexander B. Campbell Airport (YYG)
8.6/10 Excellent! (1,010 reviews)
Staff were very accommodating
Nice breakfast
Rooms weren’t overly large and extremely limited counter space in the bathroom
Comfy beds !
If traveling with pets - limited green space great location
Reviewed on Sep 28, 2026
The Arts Hotel
Downtown Charlottetown
$1,030
per person
Nov 1 - Nov 7
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Charlottetown Alexander B. Campbell Airport (YYG)
8.4/10 Very Good! (1,257 reviews)
Great location. Staff were fabulous. As long as you are aware that it is a minimalist hotel (read no tv, hair dryer etc) you’re in for a comfy and enjoyable stay in a great little hotel.
Reviewed on Sep 28, 2026
Chepstow Hotel Deals
The Barn at Spry Point
222 Ark Lane Lot B The Barn Little Pond PE
Fully refundableReserve now, pay when you stay
$84 nightly
$97 total
Sep 29 - Sep 30
Total with taxes and fees
9.2/10 Wonderful! (109 reviews)
"We were very satisfied with our stay at the barn. The staff were very friendly and helpful"
Reviewed on Sep 25, 2026
Johnson Shore Inn
9984 Northside Road, Route 16 Rock Barra PE
$141 nightly
$163 total
Oct 5 - Oct 6
Total with taxes and fees
9.8/10 Exceptional! (260 reviews)
"Well located with overlooking cliffs and 15 min from Souris. Hosts extremely helpful."
Reviewed on Sep 15, 2026
Gateway to Greenwich Suites
5560 Rte 2 Saint Peters Bay PE
Fully refundableReserve now, pay when you stay
$202 nightly
$233 total
Sep 29 - Sep 30
Total with taxes and fees
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 |
Top Sights | Basin Head Provincial Park, Red Point Provincial Park and Basin Head Fisheries Museum |
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Frequently asked questions
How much does a Chepstow vacation package cost?
Offering great value package deals from $1,016 on Expedia, you'll be pleasantly surprised at how much a vacation to Chepstow costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Chepstow?
You're likely to find reduced prices and better availability in November, December and January. Check out our cheap Chepstow vacation packages and you could land some great off-season deals.
How many days is enough for Chepstow?
With a well-organized travel plan, you can easily tick off the most popular Chepstow attractions in a handful of days. But if you'd like to discover hidden spots or go on day tours, consider booking your Chepstow vacation 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 traveling on a weekday, when prices are typically lower.
Is it cheaper to book a Chepstow vacation as a package?
Expedia vacation 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 vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation 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.
Does Expedia offer Book Now, Pay Later Chepstow vacation packages?
If you're like us, you love going away but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Chepstow trip over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure great 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.