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.
Rodd Charlottetown

Rodd Charlottetown

4.5 out of 5
Downtown Charlottetown
Price was CA $1,059, price is now CA $906 per person
CA $906
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Charlottetown Alexander B. Campbell Airport (YYG)
8.8/10 Excellent! (1,003 reviews)
its was good

Reviewed on Jul 12, 2026

Microtel Inn & Suites by Wyndham Summerside

Microtel Inn & Suites by Wyndham Summerside

3 out of 5
Price was CA $1,359, price is now CA $1,144 per person
CA $1,144
per person
Sep 12 - Sep 18
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Charlottetown Alexander B. Campbell Airport (YYG)
9.2/10 Wonderful! (626 reviews)
After a disappointing experience at another property on PEI, we rebooked at Wyndham Suites and couldn’t be happier. From the moment we arrived, Paula at the front desk made us feel like old friends. She was so warm, welcoming, and helpful. Our room is comfortable, and we immediately felt relaxed and at home. There was coffee and tea available anytime. Nice breakfast every morning. We are very grateful for the kindness we received and are looking forward to enjoying the rest of our stay on beautiful Prince Edward Island. Thank you, Paula, for turning our day around and making us feel so welcome!

Reviewed on Jul 11, 2026

The Hotel on Pownal

The Hotel on Pownal

2.5 out of 5
Downtown Charlottetown
Price was CA $1,291, price is now CA $1,110 per person
CA $1,110
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Charlottetown Alexander B. Campbell Airport (YYG)
8.8/10 Excellent! (1,004 reviews)
If you’re charged for anything extra, you will not know until you go home and happen to check the credit card. It won’t be mentioned at check out at all. If you need to talk to management, they will simply ignore your message and will not respond at all.

Reviewed on Jul 9, 2026

The Great George

The Great George

5 out of 5
Downtown Charlottetown
Price was CA $1,606, price is now CA $1,452 per person
CA $1,452
per person
Aug 16 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Charlottetown Alexander B. Campbell Airport (YYG)
9.6/10 Exceptional! (1,004 reviews)
We really enjoyed our weekend at the Great George. Lovely property, very friendly staff and a great breakfast. We will definitely stay there again.

Reviewed on Jul 12, 2026

Rodd Brudenell River

Rodd Brudenell River

4 out of 5
Price was CA $1,136, price is now CA $1,029 per person
CA $1,029
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Charlottetown Alexander B. Campbell Airport (YYG)
9/10 Wonderful! (1,001 reviews)
Pretty location and convenient for exporing East PEI. Particularly if a golfer.

Reviewed on Jul 12, 2026

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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 $319 per night from Jul 19 to Jul 20
CA $319
CA $367 total
Jul 19 - Jul 20
includes taxes & fees
8.6/10 Excellent! (807 reviews)
"Would recommend a bath mat for the tub when taking a shower, almost slipped and fell."

Reviewed on Jul 13, 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
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Ocean Privacy on a secluded beachfront cottage on 16 acres of land!!!
BH Beach House

BH Beach House

Saint Louis PE
9.8/10 Exceptional! (16 reviews)
"This house is located in a beautiful location on PEI. The direct access to what seemed almost like a private beach was the highlight of the house for us. Due to it's location at the far end of the island it did mean a lot of driving to see the other parts of the island. The kids loved the games in ..."

Reviewed on Jul 8, 2026

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BH Beach House
See all 57 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.
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Frequently asked questions

How much does an O'Leary vacation package cost?
You'll find cheap prices from CA $906 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.