O'Leary Vacations from $750

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Your OLeary Vacation

The small-town feel and friendly locals are just the start of the things OLeary has on offer. Experience the very best of this city the way you want with a customized OLeary vacation package. Want to start exploring your surroundings? Mill River Golf Course, Prince Edward Island Potato Museum and Bloomfield Provincial Park are a few of the top-rated places to visit during a trip to OLeary. Check out Expedia's extensive range of travel options and start organizing your ultimate vacation to OLeary today.

The Latest O'Leary vacation packages

Price found within the past 48 hours. Click for updated prices.
Rodd Charlottetown

Rodd Charlottetown

4.5 out of 5
Downtown Charlottetown
Price was $814, price is now $750 per person
$750
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Charlottetown (YYG)
8.8/10 Excellent! (1,006 reviews)
I can highly recommend this Hotel, it was just perfect.

Reviewed on Mar 17, 2026

The Holman Grand Hotel

The Holman Grand Hotel

4 out of 5
Downtown Charlottetown
Price was $1,071, price is now $957 per person
$957
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Charlottetown (YYG)
9.4/10 Exceptional! (1,004 reviews)
The RUSTIC GRILLE is very nice. Good cocktails. The room was very clean and well appointed but I ask for a corner room if you want quiet. Pool nice and warm and clean.

Reviewed on Mar 16, 2026

The Hotel on Pownal

The Hotel on Pownal

2.5 out of 5
Downtown Charlottetown
Price was $835, price is now $760 per person
$760
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Charlottetown (YYG)
8.8/10 Excellent! (1,008 reviews)
THE Most comfortable bed I have ever slept on in a hotel!! We were in a superior double room, ground floor, that was accessed from outside. The room was spacious and clean. The bathroom was a decent size but the toilet was tiny and uncomfortable, which isn't a huge deal. The location is great, as it's walking distance to all the shops, restaurants, pubs that are located downtown, and the Confed Centre. The deluxe continental breakfast on a Tuesday morning was good. Hot food included a frittata and breakfast sausages. There was also muffins, cereal, bagels, yogurt, oatmeal. Overall a great stay and would recommend!

Reviewed on Mar 11, 2026

The Sydney Boutique Inn

The Sydney Boutique Inn

5 out of 5
Downtown Charlottetown
Price was $923, price is now $841 per person
$841
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Charlottetown (YYG)
9.8/10 Exceptional! (1,009 reviews)
Unfortunately the tv in our room would not connect to the network so Netflix and YouTube would not work.

Reviewed on Mar 17, 2026

The Great George

The Great George

5 out of 5
Downtown Charlottetown
Price was $906, price is now $827 per person
$827
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Charlottetown (YYG)
9.6/10 Exceptional! (1,005 reviews)
Staff was very focused on ensuring guest experience was the best as possible.

Reviewed on Mar 22, 2026

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Discover the most popular places to visit in O'Leary

Prince Edward Island Potato Museum

5/5(3 reviews)

You can spend an afternoon browsing the exhibits at Prince Edward Island Potato Museum during your travels in O'Leary. Discover the restaurants in this family-friendly area, or seek out the golf courses.

Prince Edward Island Potato Museum

O'Leary Hotel Deals

Mill River Resort

Mill River Resort

3.5 out of 5
180 Mill River Resort Road, Route 136 Woodstock PE
Fully refundableReserve now, pay when you stay
$150 nightly
The price is $173 total per night from Mar 29 to Mar 30
$173 total
Mar 29 - Mar 30
Total with taxes and fees
8.6/10 Excellent! (783 reviews)
Great winter experience with the family. Set the resort up well for the young kids!

Reviewed on Mar 22, 2026

Mill River Resort
Ocean Privacy on a secluded beachfront cottage on 16 acres of land!!!

Ocean Privacy on a secluded beachfront cottage on 16 acres of land!!!

Coleman PE
Get rates
Ocean Privacy on a secluded beachfront cottage on 16 acres of land!!!
Riverside Landing Cottage

Riverside Landing Cottage

Alberton PE
10/10 Exceptional! (4 reviews)
New and clean, nice location, big hot tub, kayaks were fun, lovely deck right at the riverside.

Reviewed on Sep 5, 2025

Get rates
Riverside Landing Cottage
See all 53 properties in O'Leary
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 O'Leary Vacation Packages

OLeary Essential Information

Language
English
Currency
Canadian dollars
Max Temp Winter
25ºF
Max Temp Summer
70ºF
Top Sights
Cedar Dunes Provincial Park, West Point Lighthouse and Mill River Golf Course

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Frequently asked questions

How much does an O'Leary vacation package cost?
You can pick up a vacation package to this popular destination from $750 on Expedia. But how much your vacation to O'Leary costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to O'Leary?
You can generally find lower prices and greater availability in November, December and January. Explore our cheap O'Leary vacation packages and you could score some excellent off-season deals.
How many days is enough for O'Leary?
The ideal duration for your O'Leary vacation depends on what you'd like to do and see. Typically, a handful of days to a week will give you time to visit all the main sights and discover some hidden treasures along the way.
How to find the best O'Leary package deals?
Begin your search for an O'Leary package deal by entering your destination and preferred trip dates under our "Packages" tab. Then apply some filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal O'Leary package deal right away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your O'Leary adventure underway.
Is it cheaper to book an O'Leary vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and hotels separately. Better still, you can customize your O'Leary getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to O'Leary?
If you have your O'Leary travel dates locked in, book as early as you can to score some terrific deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are great for traveling on a whim.
Does Expedia offer Book Now, Pay Later O'Leary vacation packages?
Secure your perfect escape to O'Leary with help from our Book Now, Pay Later vacations. There's no need to save up or wait for the next payday — we've joined forces with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans let you split the cost over 3, 6 or 12 months. With no hidden or late payment fees, you can easily stay on budget and snap up bargains before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.