Chepstow Vacations from $1,264

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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.
Montgomery Cavendish Cottages

Montgomery Cavendish Cottages

3.5 out of 5
Price was $1,528, price is now $1,264 per person
$1,264
per person
Jun 7 - Jun 13
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Charlottetown (YYG)
9.8/10 Exceptional! (46 reviews)
cute spot and very clean and well maintained

Reviewed on Sep 14, 2025

The Hotel on Pownal

The Hotel on Pownal

2.5 out of 5
Downtown Charlottetown
Price was $2,373, price is now $1,972 per person
$1,972
per person
Jul 12 - Jul 18
found 4 hours ago
Roundtrip flight included
Chattanooga (CHA) to Charlottetown (YYG)
8.8/10 Excellent! (1,002 reviews)
Felt front desk staff could have been more attentive ..2 of them didn’t know where ice machine was and the complimentary coffee had ran out so I mentioned I’d come back shortly and she didn’t refill …

Reviewed on May 6, 2026

Rodd Charlottetown

Rodd Charlottetown

4.5 out of 5
Downtown Charlottetown
Price was $1,699, price is now $1,473 per person
$1,473
per person
Jun 7 - Jun 13
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Charlottetown (YYG)
8.8/10 Excellent! (1,003 reviews)
Love the history of this property. Close to everything downtown and we were able to walk everywhere we needed to go. Property was clean and the staff were very helpful

Reviewed on May 1, 2026

Fairholm Boutique Inns

Fairholm Boutique Inns

5 out of 5
Downtown Charlottetown
Price was $2,325, price is now $2,053 per person
$2,053
per person
Jul 12 - Jul 18
found 4 hours ago
Roundtrip flight included
Chattanooga (CHA) to Charlottetown (YYG)
9.2/10 Wonderful! (618 reviews)
Beautiful Inn. Staff are very nice and the breakfast was great!!!

Reviewed on Apr 7, 2026

Loyalist Country Inn & Conference Centre

Loyalist Country Inn & Conference Centre

3.5 out of 5
Price was $2,004, price is now $1,775 per person
$1,775
per person
Jul 12 - Jul 18
found 4 hours ago
Roundtrip flight included
Chattanooga (CHA) to Charlottetown (YYG)
8.4/10 Very Good! (1,376 reviews)
The property was well Maintained. What you would expect from an Inn. Breakfast was good. On the water. There was one staff member who was rude. But everyone else was lovely.

Reviewed on May 3, 2026

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Chepstow Hotel Deals

The Barn at Spry Point

The Barn at Spry Point

2 out of 5
222 Ark Lane Lot B The Barn Little Pond PE
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $100 total per night from May 18 to May 19
$100 total
May 18 - May 19
Total with taxes and fees
9/10 Wonderful! (66 reviews)
Lovely stay -- beautiful setting, helpful proprietor, comfortable accomodations.

Reviewed on Nov 23, 2025

The Barn at Spry Point
Wheelhouse Inn: Unit #3

Wheelhouse Inn: Unit #3

Georgetown PE
$126 nightly
The price is $145 total per night from May 9 to May 10
$145 total
May 9 - May 10
Total with taxes and fees
Wheelhouse Inn: Unit #3
Gateway to Greenwich Suites

Gateway to Greenwich Suites

3 out of 5
5560 Rte 2 Saint Peters Bay PE
$210 nightly
The price is $241 total per night from Jun 6 to Jun 7
$241 total
Jun 6 - Jun 7
Total with taxes and fees
8.6/10 Excellent! (110 reviews)
Clean rooms, friendly staff, and in a beautiful location on the bay. Cannot recommend enough

Reviewed on Nov 4, 2025

Gateway to Greenwich Suites
See all 117 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
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 $1,264 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.