Chepstow Vacation Packages

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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.

Top Chepstow Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Hotel on Pownal

The Hotel on Pownal

2.5 out of 5
Downtown Charlottetown
Price was CA $1,198, price is now CA $1,087 per person
CA $1,087
per person
Jan 1 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Charlottetown Alexander B. Campbell Airport (YYG)
8.6/10 Excellent! (1,015 reviews)
The hotel was in walking distance to historic Charlottetown. Restaurants close by. Clean comfortable room. Staff very helpful. Breakfast was good.

Reviewed on Oct 31, 2026

The Great George

The Great George

5 out of 5
Downtown Charlottetown
Price was CA $1,257, price is now CA $1,119 per person
CA $1,119
per person
Jan 1 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Charlottetown Alexander B. Campbell Airport (YYG)
9.6/10 Exceptional! (1,006 reviews)
This is our favourite place to stay in Charlottetown. This was the first time staying in the main building and I would not do it again only because there was a lot of wind noise from the windows and it kept me up most of the night. All my past stays at the GG have been amazing so I will be back but will not stay in the main building.

Reviewed on Oct 30, 2026

Blackbush Beach Resort

Blackbush Beach Resort

4.5 out of 5
Price was CA $1,235, price is now CA $1,126 per person
CA $1,126
per person
Jan 1 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Charlottetown Alexander B. Campbell Airport (YYG)
9.6/10 Exceptional! (591 reviews)
Disappointed when asked for a late checkout and was denied even if the hotel was almost empty!

Reviewed on Oct 30, 2026

The Holman Grand Hotel

The Holman Grand Hotel

4 out of 5
Downtown Charlottetown
Price was CA $1,285, price is now CA $1,203 per person
CA $1,203
per person
Jan 1 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Charlottetown Alexander B. Campbell Airport (YYG)
9.4/10 Exceptional! (1,010 reviews)
Only down fall was lots of kids in the pool, it was loud , and only 1 parent for probably 15 kids

Reviewed on Oct 30, 2026

The Sydney Boutique Inn

The Sydney Boutique Inn

5 out of 5
Downtown Charlottetown
Price was CA $1,367, price is now CA $1,281 per person
CA $1,281
per person
Jan 1 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Charlottetown Alexander B. Campbell Airport (YYG)
9.8/10 Exceptional! (1,006 reviews)
Great

Reviewed on Oct 30, 2026

Ready to book your vacation to Chepstow?

 

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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
9.2/10 Wonderful! (115 reviews)
"The rooms are adorable. The common space such as kitchen and bathrooms are great."

Reviewed on Oct 31, 2026

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The Barn at Spry Point
Gateway to Greenwich Suites

Gateway to Greenwich Suites

3 out of 5
5560 Rte 2 Saint Peters Bay PE
The price is CA $286 per night from Nov 1 to Nov 2
CA $286
CA $329 total
Nov 1 - Nov 2
includes taxes & fees
Gateway to Greenwich Suites
Chapel Suites - King Suite

Chapel Suites - King Suite

Souris PE
The price is CA $169 per night from Nov 1 to Nov 2
CA $169
CA $227 total
Nov 1 - Nov 2
includes taxes & fees
9.6/10 Exceptional! (80 reviews)
"Beautiful place. Comfortable bed and pillows. I would stay there again."

Reviewed on Oct 16, 2026

Chapel Suites - King Suite
See all 116 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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Frequently asked questions

How much does a Chepstow vacation package cost?
Offering excellent value package deals from CA $1,087 on Expedia, you'll be thrilled with how little a vacation to Chepstow costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Chepstow?
To score cheap Chepstow vacation packages, plan your trip outside of peak periods such as school holidays. You'll generally find lower prices and better availability in the off-season or when it's less busy.
How many days is enough for Chepstow?
Chepstow vacations come in many shapes and sizes, but to really get a feel for this place, we'd suggest 2 days is a good ballpark. This will mean you can visit major attractions like The Myriad View Artisan Distillery and Rollo Bay Greens as well as underrated spots. Don't skip cool areas such as Saint Catherines and Lot 46 either. If you're smart with your time, you can even schedule a day trip outside of Chepstow too.
How to find the best Chepstow package deals?
Begin your search for a Chepstow package deal by entering your destination and preferred trip dates under our "Packages" tab. Then apply some filters, like "Guest rating" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Chepstow package deal right away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Chepstow adventure underway.
Is it cheaper to book a Chepstow vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll typically get a better deal than booking each component separately. And you'll still have the freedom to create a personalized Chepstow vacation by choosing your preferred type of stay, airline and car class.
How to plan a trip to Chepstow?

  1. Pick your travel dates: The things you want to do in Chepstow and your preferred season will help you decide when to travel.
  2. Plan your budget wisely: As well as the cost of your hotel, you'll need to consider other expenses. These include food, transportation and flights. Also, put aside some extra funds for unexpected expenses that may crop up during your trip to Chepstow.
  3. Determine how many days away: Start by making a list of all the activities and sights you want to experience in Chepstow. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to choose a Chepstow vacation package that brings all your bookings together.

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