Chepstow Vacations from $877

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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.
Fair Isle Motel

Fair Isle Motel

2.5 out of 5
Price was $1,101, price is now $877 per person
$877
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) to Charlottetown (YYG)
8.4/10 Very Good! (533 reviews)
Nice room and amenities for 2 night stay

Reviewed on Oct 3, 2025

The Great George

The Great George

5 out of 5
Downtown Charlottetown
Price was $1,247, price is now $932 per person
$932
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) to Charlottetown (YYG)
9.8/10 Exceptional! (1,017 reviews)
Best Hotel I ever stayed in. Free happy hour, great staff, great ambiance, wonderful rooms. Just perfect.

Reviewed on Oct 3, 2025

The Hotel on Pownal

The Hotel on Pownal

2.5 out of 5
Downtown Charlottetown
Price was $1,197, price is now $902 per person
$902
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) to Charlottetown (YYG)
8.8/10 Excellent! (1,010 reviews)
Walkable to shops and restaurants. Great Irish bar in area. Water prince lobster restaurant was excellent for seafood. Staff at hotel excellent!

Reviewed on Oct 3, 2025

Fairholm Boutique Inns

Fairholm Boutique Inns

5 out of 5
Downtown Charlottetown
Price was $1,252, price is now $986 per person
$986
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) to Charlottetown (YYG)
9.2/10 Wonderful! (594 reviews)
Great location and very comfortable place to stay. Would go there again.

Reviewed on Sep 28, 2025

Wild Pines Cabins

Wild Pines Cabins

2 out of 5
Price was $1,128, price is now $900 per person
$900
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) to Charlottetown (YYG)
9.8/10 Exceptional! (20 reviews)
What a lovely spot..

Reviewed on Aug 29, 2025

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Chepstow Hotel Deals

Singing Sands Inn Motel

Singing Sands Inn Motel

2.5 out of 5
2518 East Point Road – RTE 16, Kingsboro, Kingsboro, PE
7.4/10 Good! (145 reviews)
"Rapport qualité/prix"

Reviewed on Sep 20, 2025

Get rates
Singing Sands Inn Motel
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
$82 nightly
The price is $95 total per night from Oct 5 to Oct 6
$95 total
Oct 5 - Oct 6
Total with taxes and fees
8.8/10 Excellent! (61 reviews)
"It was delightful!! Clean, warm & comfortable. The nature walks and views were stunning! Would love to return and visit The Barn again!!! A big Thank you to Dave and your staff!"

Reviewed on Sep 25, 2025

The Barn at Spry Point
Johnson Shore Inn

Johnson Shore Inn

3 out of 5
9984 Northside Road, Route 16, Rock Barra, PE
$136 nightly
The price is $156 total per night from Oct 5 to Oct 6
$156 total
Oct 5 - Oct 6
Total with taxes and fees
9.6/10 Exceptional! (237 reviews)
"The view was amazing, beautiful quiet spot. The owner and staff were wonderful. Breakfast was very good with homemade jam, I even got the recipe. Thankyou Mellanie! Amazing sunrise view from our room. Couldn't have had a better stay on PEI."

Reviewed on Oct 1, 2025

Johnson Shore Inn
See all 105 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.

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 $877 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.