O'Leary Vacations from $846

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Lily's Garden

Lily's Garden

4 out of 5
West Royalty
Price was $1,016, price is now $846 per person
$846
per person
Aug 22 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Charlottetown Alexander B. Campbell Airport (YYG)
7.8/10 Good! (154 reviews)
Tina was amazing and very friendly. the place was clean and organized, it was a great stay

Reviewed on Jun 28, 2026

Multicultural Museum Cottages

Multicultural Museum Cottages

3 out of 5
Price was $1,033, price is now $849 per person
$849
per person
Aug 22 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Charlottetown Alexander B. Campbell Airport (YYG)
9/10 Wonderful! (50 reviews)
Good location, had lots of space for our group.

Reviewed on Jun 30, 2026

Anne Shirley Motel & Cottages

Anne Shirley Motel & Cottages

2 out of 5
Price was $1,030, price is now $850 per person
$850
per person
Aug 22 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Charlottetown Alexander B. Campbell Airport (YYG)
6.6/10 (282 reviews)
Clean room. Quick to answer questions. Only disappointed as there was nothing really included besides just night rest. We booked it thinking it was a bed and breakfast but it wasn't.

Reviewed on Jul 2, 2026

Stanley Bridge Country Resort

Stanley Bridge Country Resort

2 out of 5
Price was $1,079, price is now $891 per person
$891
per person
Aug 22 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Charlottetown Alexander B. Campbell Airport (YYG)
8/10 Very Good! (65 reviews)
Rooms were clean. The staff were friendly, but if they would invest in their money into some updates to the rooms.

Reviewed on Jul 3, 2026

Silverwood Motel

Silverwood Motel

3.5 out of 5
Price was $1,055, price is now $882 per person
$882
per person
Aug 22 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Charlottetown Alexander B. Campbell Airport (YYG)
8/10 Very Good! (446 reviews)
Loved the breakfast room. Staff were great. The view from our room was beautiful.

Reviewed on Jul 3, 2026

Don't see what you're looking for?
See all available trips from Columbus to O'Leary
View all trips

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

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
$202 nightly
The price is $233 total per night from Jul 7 to Jul 8
$233 total
Jul 7 - Jul 8
Total with taxes and fees
8.6/10 Excellent! (802 reviews)
"The main complaint was that the air conditioning made the hotel very cold. The dining room and bar were uncomfortably cold. Outside it was 31 degrees and inside may be 17. Our room was extremely cold and we had to actually heat the room to make it comfortable. Our room was down to 64 F. The staff ..."

Reviewed on Jul 4, 2026

Mill River Resort
BH Beach House

BH Beach House

Saint Louis PE
9.8/10 Exceptional! (15 reviews)
"Beautiful beach house on a large property. The bedrooms are lovely and there is lots of areas for relaxing and playing games. The hot tub was great and there was plenty of outdoor seating. A quick walk down the back yard takes you to stairs to the beach which was sandy and quite private. A nice bonus ..."

Reviewed on Jun 29, 2026

Get rates
BH Beach House
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
Get rates
Ocean Privacy on a secluded beachfront cottage on 16 acres of land!!!
See all 56 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does an O'Leary vacation package cost?
You can pick up a vacation package to this popular destination from $846 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.