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.
Microtel Inn & Suites by Wyndham Antigonish

Microtel Inn & Suites by Wyndham Antigonish

4.5 out of 5
per person
Sep 21 - Sep 24
found 2 hours ago
Roundtrip flight included
Toronto (YYZ) to Charlottetown (YYG)
9.4/10 Exceptional! (618 reviews)
Clean, good location and friendly staff.

Reviewed on Jul. 18, 2025

Clinton Pond Bed and Breakfast

Clinton Pond Bed and Breakfast

4 out of 5
Save 100% on your flight
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Charlottetown (YYG)
9.8/10 Exceptional! (8 reviews)
Loyalist Country Inn & Conference Centre

Loyalist Country Inn & Conference Centre

3.5 out of 5
Save 100% on your flight
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Charlottetown (YYG)
8.4/10 Very Good! (1,122 reviews)
Properly is nice, could use a few updates, the staff are friendly and knowledgeable. Parking is good, not far from shopping and restaurants

Reviewed on Jul. 18, 2025

Sunflower Guest Suites

Sunflower Guest Suites

3 out of 5
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Charlottetown (YYG)
8.4/10 Very Good! (53 reviews)
A perfectly lovey place to stay in summerside. Great service and clean newer rooms. It’s about a 10min walk from the main drag in summerside and the waterfront action. If you want a nice easy stay this is the place.

Reviewed on Jul. 19, 2025

Pine Cottages

Pine Cottages

2 out of 5
per person
Sep 12 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Charlottetown (YYG)
6.8/10 (8 reviews)
During our whole stay they were great at communicating with us if we had questions or concerns. The cabin was cozy, clean and well maintained. Will definitely be going back!

Reviewed on Jul. 18, 2025

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Chepstow Hotel Deals

Charming PEI farmhouse with beach access

Charming PEI farmhouse with beach access

Souris
10/10 Exceptional! (1 review)
"Lovely house with a great view above a fine beach. Good swimming and lots of wildlife. Eagles, foxes, seals and porpoises. Close to town but very quiet."

Reviewed on Jul. 13, 2025

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Charming PEI farmhouse with beach access
The Barn at Spry Point

The Barn at Spry Point

2 out of 5
222 Ark Lane Lot B The Barn, Little Pond, PE
The price is CA $128 per night from Jul 21 to Jul 22
CA $128
CA $147 total
Jul 21 - Jul 22
includes taxes & fees
8.6/10 Excellent! (31 reviews)
Splendid isolation
"This is a very nice place to relax and take it easy. Note, if more than two rooms are occupied, one bathroom will need to be shared. The "barn" is very quirky with bedrooms, bathrooms, living room, large kitchen but this is what makes it charming. If one wants to spend a night in splendid isolation, ..."

Reviewed on Jul. 14, 2025

The Barn at Spry Point
Johnson Shore Inn

Johnson Shore Inn

3 out of 5
9984 Northside Road, Route 16, Rock Barra, PE
The price is CA $225 per night from Jul 21 to Jul 22
CA $225
CA $259 total
Jul 21 - Jul 22
includes taxes & fees
9.6/10 Exceptional! (212 reviews)
"Beautiful vista. Nice, clean rooms/house. Great breakfast. Nice hosts"

Reviewed on Jul. 14, 2025

Johnson Shore Inn
See all 124 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

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Frequently asked questions

How much does a Chepstow vacation package cost?
Offering excellent value package deals from CA $559 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.