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 Hotel on Pownal

The Hotel on Pownal

2.5 out of 5
Downtown Charlottetown
Price was CA $1,125, price is now CA $1,020 per person
CA $1,020
per person
Jan 7 - Jan 10
found 12 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Charlottetown Alexander B. Campbell Airport (YYG)
8.6/10 Excellent! (1,015 reviews)
La majorité des commodités étaient bonnes. Les oreillers étaient un peu trop hauts.

Reviewed on Oct 28, 2026

The Great George

The Great George

5 out of 5
Downtown Charlottetown
Price was CA $1,170, price is now CA $1,065 per person
CA $1,065
per person
Jan 7 - Jan 10
found 12 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Charlottetown Alexander B. Campbell Airport (YYG)
9.6/10 Exceptional! (1,006 reviews)
Perfect in every way

Reviewed on Oct 28, 2026

The Sydney Boutique Inn

The Sydney Boutique Inn

5 out of 5
Downtown Charlottetown
Price was CA $1,260, price is now CA $1,165 per person
CA $1,165
per person
Jan 7 - Jan 10
found 12 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Charlottetown Alexander B. Campbell Airport (YYG)
9.8/10 Exceptional! (1,006 reviews)
Everything down to the little details were perfect for our honeymoon. Will definitely return!

Reviewed on Oct 29, 2026

The Holman Grand Hotel

The Holman Grand Hotel

4 out of 5
Downtown Charlottetown
Price was CA $1,172, price is now CA $1,093 per person
CA $1,093
per person
Jan 7 - Jan 10
found 12 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Charlottetown Alexander B. Campbell Airport (YYG)
9.4/10 Exceptional! (1,010 reviews)

Blackbush Beach Resort

Blackbush Beach Resort

4.5 out of 5
Price was CA $1,123, price is now CA $1,050 per person
CA $1,050
per person
Jan 7 - Jan 10
found 12 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Charlottetown Alexander B. Campbell Airport (YYG)
9.6/10 Exceptional! (591 reviews)

Ready to book your vacation to O'Leary?

 

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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
The price is CA $177 per night from Nov 29 to Nov 30
CA $177
CA $204 total
Nov 29 - Nov 30
includes taxes & fees
8.6/10 Excellent! (888 reviews)
"Beautiful first impression driving in through the fall trees on the way in. Was given a free upgrade to corner suite over golf course. Musky smelling, sink didn't drain,kleenex box empty,windows all smeared and foggy not what I expected for a resort on our anniversary trip around pei"

Reviewed on Oct 26, 2026

Mill River Resort
Beachfront, sandbar, 8p sauna, pickleball court, 6BR, outdoor kitchen and more

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

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Beachfront, sandbar, 8p sauna, pickleball court, 6BR, outdoor kitchen and more
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
9.8/10 Exceptional! (6 reviews)
"Excellent property with views of the ocean. Close to the beach and private."

Reviewed on Sep 6, 2026

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Ocean Privacy on a secluded beachfront cottage on 16 acres of land!!!
See all 58 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.
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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.
See properties

Frequently asked questions

How much does an O'Leary vacation package cost?
You'll find cheap prices from CA $1,020 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?

  1. Choose your travel dates: The things you plan to do in O'Leary and your preferred season can help you decide when to go.
  2. 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.
  3. 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.
  4. 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.