Chepstow Vacations from ￥315,115

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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
per person
Sep 28 - Oct 3
found 1 day ago
Roundtrip flight included
Hiroshima (HIJ) to Charlottetown (YYG)
9.6/10 Exceptional! (38 reviews)
The only down side was the beds were very hard and the hide a bed wasnt able to be slept on due to condition. Otherwise the property was very nice and clean. The kitchen had everything you would need and deck was wonderful to sit on while using the provided BBQ. Management was very friendly and check in was a breeze.

Reviewed on Jun 29, 2025

The Hotel on Pownal

The Hotel on Pownal

2.5 out of 5
Downtown Charlottetown
per person
Sep 28 - Oct 3
found 1 day ago
Roundtrip flight included
Hiroshima (HIJ) to Charlottetown (YYG)
8.8/10 Excellent! (1,001 reviews)
Great property and walking distance to everything near the waterfront.

Reviewed on Jul 24, 2025

The Holman Grand Hotel

The Holman Grand Hotel

4 out of 5
Downtown Charlottetown
per person
Sep 28 - Oct 3
found 1 day ago
Roundtrip flight included
Hiroshima (HIJ) to Charlottetown (YYG)
9.4/10 Exceptional! (1,012 reviews)
This was such a lovely stay - highly recommend! Excellent location, convenient walk from downtown Charlottetown restaurants, sights and waterfront. Spacious rooms! Knowledgeable and welcoming staff made the visit memorable! There are some rooms which also face the water - see if you can request one for a fantastic view! If you are driving, downtown Charlottetown parking can be challenging to find so I recommend getting valet parking, leaving your car and then exploring downtown!

Reviewed on Jul 25, 2025

The Great George

The Great George

5 out of 5
Downtown Charlottetown
per person
Sep 28 - Oct 3
found 1 day ago
Roundtrip flight included
Hiroshima (HIJ) to Charlottetown (YYG)
9.8/10 Exceptional! (1,008 reviews)
Such a unique boutique hotel with plenty of vintage decor. The breakfast was amazing and the happy hour free drinks each evening were a great touch for socializing guests.

Reviewed on Jul 25, 2025

The Harbour House

The Harbour House

4 out of 5
Downtown Charlottetown
per person
Sep 28 - Oct 3
found 1 day ago
Roundtrip flight included
Hiroshima (HIJ) to Charlottetown (YYG)
9.4/10 Exceptional! (950 reviews)
We thoroughly enjoyed our stay here. The room was cozy and quiet. Comfortable bed and a nice little kitchen. The breakfast was fabulous and everyone was helpful and pleasant.

Reviewed on Jul 21, 2025

Find the Best Chepstow Vacation Packages

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

Get rates
Charming PEI farmhouse with beach access
Johnson Shore Inn

Johnson Shore Inn

3 out of 5
9984 Northside Road, Route 16, Rock Barra, PE
The price is ￥24,250 per night from Aug 6 to Aug 7
￥24,250
￥27,888 total
Aug 6 - Aug 7
includes taxes & fees
9.6/10 Exceptional! (214 reviews)
Exceptional, delightful!
"Staying at the Johnson Shore Inn truly felt like a home away from home. We especially enjoyed winding down each day in the cozy dining room, savouring delicious meals and great conversations with fellow guests. Our room was beautifully decorated, peaceful, and offered a perfect place to relax. The ..."

Reviewed on Jul 24, 2025

Johnson Shore Inn
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
The price is ￥12,394 per night from Aug 1 to Aug 2
￥12,394
￥14,253 total
Aug 1 - Aug 2
includes taxes & fees
8.6/10 Excellent! (35 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
See all 121 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.

Frequently asked questions

How much does a Chepstow vacation package cost?
Offering great value package deals from ￥315,115 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?
To pick up cheap Chepstow vacation packages, organize your getaway outside of peak times 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?
With a well-planned schedule, you can easily visit the most popular Chepstow sights in a handful of days. But if you'd like to discover lesser-known spots or take day trips, 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.
How to plan a trip to Chepstow?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to travel to Chepstow.
  2. Plan your budget wisely: Besides the price of your hotel, you should consider other expenses too. These include food, transportation and flights. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Chepstow.
  3. Decide your trip length: Consider how long you want to spend exploring Chepstow. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Combine your accommodations and airfare: After you've settled on your travel dates and duration, lock in the right Chepstow vacation package for you.

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