O'Leary Vacation Packages
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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.
Top O'Leary Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Harbour House
Downtown Charlottetown
CA $1,078
per person
Nov 20 - Nov 27
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Charlottetown Alexander B. Campbell Airport (YYG)
9.4/10 Exceptional! (1,002 reviews)
To start with, the room was clean and bright. The breakfast was unexpectedly good because they offered a vegan breakfast which aligns with our preferred way of eating. And that they had laundry facilities on the lower level wrapped everything together for a pleasant stay.
Reviewed on Sep 9, 2026
The Great George
Downtown Charlottetown
CA $1,226
per person
Nov 20 - Nov 27
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Charlottetown Alexander B. Campbell Airport (YYG)
9.6/10 Exceptional! (1,008 reviews)
My husband and I had such a wonderful 2-night stay at The Great George!! Such lovely and helpful staff, beautiful rooms, prime location, delicious breakfast :)
Reviewed on Sep 14, 2026
The Sydney Boutique Inn
Downtown Charlottetown
CA $1,399
per person
Nov 20 - Nov 27
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Charlottetown Alexander B. Campbell Airport (YYG)
9.8/10 Exceptional! (1,009 reviews)
We had a wonderful two night stay. We were very pleased with the two bedroom room. Overall it was a very spacious accommodation. Although we didn’t utilize the kitchen amenities much it would have been very useful for a family or larger party of people. The king bed was excellent and had two solid nights sleep.
Reviewed on Sep 14, 2026
Ready to book your vacation to O'Leary?
O'Leary Hotel Deals
Mill River Resort
180 Mill River Resort Road, Route 136 Woodstock PE
CA $247
CA $283 total
Oct 1 - Oct 2
includes taxes & fees
8.6/10 Excellent! (874 reviews)
"Beautiful hotel and property!"
Reviewed on Sep 9, 2026
Beachfront, sandbar, 8p sauna, pickleball court, 6BR, outdoor kitchen and more
Wellington PE
10/10 Exceptional! (8 reviews)
"Très belle semaine la maison est parfsite"
Reviewed on Aug 30, 2026
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.
Stay near popular O'Leary attractions
Prince Edward Island Potato Museum
9.0/10 (26 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.
Frequently asked questions
How much does an O'Leary vacation package cost?
You'll find cheap prices from CA $1,078 on Expedia for your O'Leary break. However, a range of factors like the hotel choice, length of stay and season will determine how much your vacation to O'Leary costs.
What are the cheapest months to go to O'Leary?
January, February and November are great times to look for cheap O'Leary vacation packages. Opting to travel in less busy periods means you can typically find reduced prices on hotels and flights.
How many days is enough for O'Leary?
The ideal duration of your O'Leary vacation depends on what you'd like to see. Typically, a few days to a week will give you plenty of time to go to all the leading sights and explore some hidden treasures along the way.
How to find the best O'Leary package deals?
Landing a cheap O'Leary package deal is a cinch with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget range, add a few filters and browse what's available. You can fine-tune your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to view the most wallet-friendly O'Leary package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book an O'Leary vacation as a package?
You can enjoy significant savings on your next O'Leary getaway by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to browse the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to O'Leary?
If you're considering a spur-of-the-moment O'Leary getaway, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can find amazing deals on your hotels and flights by booking ahead.
How to plan a trip to O'Leary?
- Choose your travel dates: The things you plan to do in O'Leary and your preferred season can help you decide when to go.
- Budget wisely: As well as the cost of your stay, you'll need to consider other expenses too. These include food, flights and transportation. Also, put aside a little extra for unexpected costs that could arise during your trip to O'Leary.
- Decide how long to go for: Now that you're up to speed on O'Leary, you can figure out the ideal length of your break. Pull together a rough itinerary and give yourself enough time to cover everything you want to see.
- Bundle your accommodations and airfare: Once you've nailed down your travel dates and duration, lock in the right O'Leary vacation package for you.
Explore a world of travel with Expedia
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- Summerside Vacations
- Union Corner Provincial Park
- Cedar Dunes Provincial Park
- Sea View Vacations
- Prince Edward Island National Park
- Eptek Art and Culture Centre
- Green Park Shipbuilding Museum & Yeo House
- French River Vacations
- Spinnaker's Landing
- Prince Edward Island Potato Museum
- West Point Lighthouse
- Visit Alma
- Burlington Amusement Park
- St. Mary's Church
- Kensington Vacations
- Bloomfield Provincial Park
- Darnley Greens Golf Course
- Avonlea Village
- Visit O'Leary
- Cape Egmont Lighthouse
- Cabot Beach Provincial Park
- Irish Moss Interpretive Centre
- Green Gables Heritage Place
- Cavendish Beach
- Linkletter Provincial Park
- Visit Cape Wolfe
- North Cape Lighthouse
- Mill River Golf Course
- Anne of Green Gables Museum
- Visit West Point
- Summerside Harbor
- Clinton Vacations
- Visit Miminegash
- Indian Head Lighthouse
- Jacques Cartier Provincial Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
