O'Leary Vacations from $905

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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.
Pine Cottages

Pine Cottages

2 out of 5
Price was $1,026, price is now $905 per person
$905
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Charlottetown (YYG)
8/10 Very Good! (18 reviews)
Lovely clean cottage with everything you need right across from the beach. Would definitely stay here again.

Reviewed on Sep 19, 2025

The Hotel on Pownal

The Hotel on Pownal

2.5 out of 5
Downtown Charlottetown
Price was $1,652, price is now $1,385 per person
$1,385
per person
Jul 14 - Jul 18
found 24 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Charlottetown (YYG)
8.8/10 Excellent! (1,009 reviews)
Raphael at the Front Desk was very helpful. The lady managing the breakfast area was very friendly, attentive and efficient.

Reviewed on May 28, 2026

Rodd Charlottetown

Rodd Charlottetown

4.5 out of 5
Downtown Charlottetown
Price was $1,447, price is now $1,279 per person
$1,279
per person
Aug 13 - Aug 16
found 24 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Charlottetown (YYG)
8.8/10 Excellent! (1,006 reviews)
Awesome customer service , hotel and rooms were spotless.

Reviewed on May 29, 2026

The Great George

The Great George

5 out of 5
Downtown Charlottetown
Price was $1,317, price is now $1,182 per person
$1,182
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Charlottetown (YYG)
9.6/10 Exceptional! (1,006 reviews)
Wonderful location, excellent room.

Reviewed on May 27, 2026

Loyalist Country Inn & Conference Centre

Loyalist Country Inn & Conference Centre

3.5 out of 5
Price was $1,147, price is now $1,040 per person
$1,040
per person
Jul 20 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Charlottetown (YYG)
8.4/10 Very Good! (1,396 reviews)
The staff were positively wonderful. The room was super clean and lovely. The pool was amazing. The lady that works in the breakfast room was fantastic.

Reviewed on May 29, 2026

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Discover the most popular places to visit in O'Leary

Prince Edward Island Potato Museum

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
$176 nightly
The price is $202 total per night from Jun 2 to Jun 3
$202 total
Jun 2 - Jun 3
Total with taxes and fees
8.6/10 Excellent! (791 reviews)
"The room was very clean and the staff were great."

Reviewed on May 25, 2026

Mill River Resort
The Little Yellow Farm House is country living, ocean views, open sky & bonfires

The Little Yellow Farm House is country living, ocean views, open sky & bonfires

Chrysostome PE
Get rates
The Little Yellow Farm House is country living, ocean views, open sky & bonfires
Foley’s Harbour House

Foley’s Harbour House

Alberton PE
$279 nightly
The price is $321 total per night from Jun 2 to Jun 3
$321 total
Jun 2 - Jun 3
Total with taxes and fees
9.8/10 Exceptional! (7 reviews)
"The house was clean, spacious and had a nice view. Brandy was very attentive and responded immediately if I had a question. We spent 2 lovely days enjoying her house and property, (lighthouse visible from the deck!) I will definitely rent this property again if we visit PEI in the future"

Reviewed on May 22, 2026

Foley’s Harbour House
See all 54 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 $905 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.