O'Leary Vacations

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Find the Best O'Leary Vacation Packages

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
8.4/10 Very Good! (654 reviews)
"Property recently underwent a total facelift and update. Enjoyed our stay."

Reviewed on Jun 15, 2025

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Mill River Resort
Briarwood Coastal Cottages & Lodge
Briarwood Coastal Cottages & Lodge
3 out of 5
253 Matthews Lane, Union, PE
8.6/10 Excellent! (196 reviews)
"Beautiful place and excellent staff."

Reviewed on May 17, 2025

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Briarwood Coastal Cottages & Lodge
Quiet peaceful getaway
Quiet peaceful getaway
2 out of 5
252 Oliver Rd, Huntley, PE
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Quiet peaceful getaway
See all 49 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.

Frequently asked questions

How much does an O'Leary vacation package cost?
You can pick up a vacation package to this popular destination 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?
January, February and November are great times to search for cheap O'Leary vacation packages. Choosing to travel in quieter periods means you can usually find better prices on flights and hotels.
How many days is enough for O'Leary?
The ideal duration of your O'Leary vacation depends on what you'd like to do and see. Usually, a handful of days to a week will give you enough time to tick off all the main sights and explore 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.
How to plan a trip to O'Leary?

  1. Pick your dates: What you want to do in O'Leary and your favorite season will help you decide when to travel.
  2. Set a budget: Factor in expenses like flights, food and transportation when calculating how much to set aside for your trip to O'Leary. Then, select a property that suits your budget, whether that's a wallet-friendly stay or a high-end retreat.
  3. Decide your trip length: Think about how long you want to spend exploring O'Leary. Plan your itinerary so you can get to all the attractions and experiences you're interested in without rushing.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to find an O'Leary vacation package that brings all your bookings together.

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