O'Leary Vacations from $678

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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.
By The Bay Cottages

By The Bay Cottages

3 out of 5
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) to Charlottetown (YYG)
8/10 Very Good! (17 reviews)
near a beautiful beach, far from restaurants and activities if you want to visit the all around island. The property is reasonable for the price. I would not go back

Reviewed on Jun 16, 2025

Pine Cottages

Pine Cottages

2 out of 5
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) to Charlottetown (YYG)
6.8/10 (8 reviews)
The Hotel on Pownal

The Hotel on Pownal

2.5 out of 5
Downtown Charlottetown
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) to Charlottetown (YYG)
8.8/10 Excellent! (1,008 reviews)
Great location - close to everything, very walkable. No elelvator and it’s a 2 story motel that’s be refurbished. Rooms are nice, bathroom was a tad small. Staff were super responsive and friendly, especially the breakfast staff at the buffet that’s included. Would stay again

Reviewed on Jul 3, 2025

The Great George

The Great George

5 out of 5
Downtown Charlottetown
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) to Charlottetown (YYG)
9.8/10 Exceptional! (1,003 reviews)
We were advised to stay here from friends. Staff here will go above and beyond - the hotel is beautiful. No issues with the rooms they were exceptionally comfortable - highly recommend coming in Charlottetown to stay here.

Reviewed on Jun 30, 2025

Quality Inn & Suites Downtown

Quality Inn & Suites Downtown

3.5 out of 5
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) to Charlottetown (YYG)
8.8/10 Excellent! (325 reviews)
We had a great stay. Checkin was quick, our room was spacious and clean. Breakfast was great. Location was very convenient, easy to walk to downtown shops and restaurants

Reviewed on Jun 30, 2025

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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
$178 nightly
The price is $205 total per night from Jul 4 to Jul 5
$205 total
Jul 4 - Jul 5
Total includes taxes and fees
8.4/10 Very Good! (657 reviews)
"Great location, beautiful golf course! Will be back!"

Reviewed on Jul 1, 2025

Mill River Resort
BH Beach House
BH Beach House
Saint Louis
9.4/10 Exceptional! (3 reviews)
Quiet beach lots of room for family
"Awesome location with everything you need for a little get away!"

Reviewed on Jun 18, 2025

Get rates
BH Beach House
Sunset View
Sunset View
Coleman
$273 nightly
The price is $313 total per night from Jul 12 to Jul 13
$313 total
Jul 12 - Jul 13
Total includes taxes and fees
Sunset View
See all 48 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 $678 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.