Cumberland Vacations from $1,668

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Your Cumberland Vacation

When a city escape is calling, answer it with a vacation package to Cumberland. With all your travel needs in place before you leave, all you need to do here is focus on making unforgettable memories. If taking in sights is on the agenda during your trip to Cumberland, stop by major attractions like University of Prince Edward Island, Confederation Centre of the Arts and Eastlink Centre. Don't delay your visit to this destination any longer. The ultimate Cumberland vacation is a couple of clicks away with Expedia.

The Latest Cumberland vacation packages

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 $1,824, price is now $1,668 per person
$1,668
per person
Dec 18 - Dec 21
found 12 hours ago
Roundtrip flight included
Portland (PWM) to Charlottetown (YYG)
8.8/10 Excellent! (1,027 reviews)
Good stay but extrêmement noise room 113 and not from humans but from pipes and watersystem. Kept us awake for 2 nights and couldn’t get a room change.

Reviewed on Oct 26, 2025

The Great George

The Great George

5 out of 5
Downtown Charlottetown
Price was $1,888, price is now $1,730 per person
$1,730
per person
Dec 18 - Dec 21
found 12 hours ago
Roundtrip flight included
Portland (PWM) to Charlottetown (YYG)
9.6/10 Exceptional! (1,024 reviews)
Fabulous hotel and staff! We had a wonderful stay. However, we felt the breakfast wasn't refreshed or restocked and many of the items had run out. Also there is not enough room for everyone to sit down.

Reviewed on Oct 26, 2025

Fairholm Boutique Inns

Fairholm Boutique Inns

5 out of 5
Downtown Charlottetown
Price was $1,892, price is now $1,738 per person
$1,738
per person
Dec 18 - Dec 21
found 12 hours ago
Roundtrip flight included
Portland (PWM) to Charlottetown (YYG)
9.2/10 Wonderful! (609 reviews)
What a beautiful place to stay in Charlottetown! Lovely historic inn on a quiet street but within a short walking distance to shops, restaurants and the waterfront. The staff were exceptional and went above and beyond. The breakfast was delicious. I would highly recommend the Fairholm Boutique Inn.

Reviewed on Oct 25, 2025

Mill River Resort

Mill River Resort

3.5 out of 5
Price was $1,925, price is now $1,770 per person
$1,770
per person
Dec 18 - Dec 21
found 12 hours ago
Roundtrip flight included
Portland (PWM) to Charlottetown (YYG)
8.6/10 Excellent! (753 reviews)
Always a wonderful stay at Mill River!

Reviewed on Oct 20, 2025

Microtel Inn & Suites by Wyndham Summerside

Microtel Inn & Suites by Wyndham Summerside

3 out of 5
Price was $1,894, price is now $1,747 per person
$1,747
per person
Dec 18 - Dec 21
found 12 hours ago
Roundtrip flight included
Portland (PWM) to Charlottetown (YYG)
9.2/10 Wonderful! (532 reviews)
Parking can be very tight due to the shared parking lot with the sports centre at the rear of hotel

Reviewed on Oct 26, 2025

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Cumberland Hotel Deals

Charlottetown Inn & Conference Centre

Charlottetown Inn & Conference Centre

3.5 out of 5
238 Grafton St, Charlottetown, PE
Fully refundableReserve now, pay when you stay
5.6/10 (1,450 reviews)
The hotel was under renovation at the time of my stay.Going to be real nice when they finish.

Reviewed on Oct 23, 2025

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Charlottetown Inn & Conference Centre
The Hotel on Pownal

The Hotel on Pownal

2.5 out of 5
146 Pownal Street, Charlottetown, PE
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $103 total per night from Nov 1 to Nov 2
$103 total
Nov 1 - Nov 2
Total with taxes and fees
8.6/10 Excellent! (1,008 reviews)
Fine for a quick overnight stay.

Reviewed on Oct 24, 2025

The Hotel on Pownal
The Great George

The Great George

5 out of 5
58 Great George St, Charlottetown, PE
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $130 total per night from Nov 12 to Nov 13
$130 total
Nov 12 - Nov 13
Total with taxes and fees
9.6/10 Exceptional! (1,039 reviews)
We had a great time. Quaint, local vibe and very inviting with a nice breakfast set up.

Reviewed on Oct 24, 2025

The Great George
See all 504 properties in Cumberland
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 Cumberland Vacation Packages

Cumberland Essential Information

Language
English
Currency
Canadian dollars
Closest Airport
Charlottetown Airport (YYG)
Top Sights
St. Dunstans Basilica, Argyle Shore Provincial Park and The Mack

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Frequently asked questions

How much does a Cumberland vacation package cost?
You can grab a vacation package to this popular destination from $1,668 on Expedia. But how much your vacation to Cumberland costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Cumberland?
November, December and January are the best times to look for cheap Cumberland vacation packages. Choosing to travel in quieter periods means you can usually find lower prices on accommodations and flights.
How many days is enough for Cumberland?
With a well-organized travel plan, you can easily hit the top Cumberland sights in a handful of days. But if you want to discover lesser-known spots or take day trips, think about booking your Cumberland vacation for longer.
How to find the best Cumberland package deals?
Use Expedia's filters to find some great Cumberland package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or look for Cumberland package deals in the low season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Cumberland vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component separately. And you'll still get the flexibility to create a customized Cumberland vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Cumberland?
If you've got your Cumberland travel dates locked in, book as early as you can to bag some outstanding deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are great for traveling on a whim.
Does Expedia offer Book Now, Pay Later Cumberland vacation packages?
Secure your dream escape to Cumberland with our Book Now, Pay Later vacations. There's no need to scrimp and save or wait until your next paycheck — we've partnered with online lender Affirm to offer you flexibility and choice. Our vacation packages with payment plans mean you can split the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to stay on budget and snap up cheap deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.