O'Leary Vacations from $1,073

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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.

The Latest O'Leary vacation packages

Price found within the past 48 hours. Click for updated prices.
Pine Cottages

Pine Cottages

2 out of 5
Price was $1,154, price is now $1,073 per person
$1,073
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Colorado Springs (COS) to Charlottetown (YYG)
7.4/10 Good! (10 reviews)
Look like the property was under renovation there was stuff laying around everywhere the bed was very uncomfortable. Good part it was very close to the beach..

Reviewed on Aug 14, 2025

Montgomery Cavendish Cottages

Montgomery Cavendish Cottages

3.5 out of 5
Price was $1,268, price is now $1,123 per person
$1,123
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Colorado Springs (COS) to Charlottetown (YYG)
9.6/10 Exceptional! (39 reviews)
The only down side was the beds were very hard and the hide a bed wasnt able to be slept on due to condition. Otherwise the property was very nice and clean. The kitchen had everything you would need and deck was wonderful to sit on while using the provided BBQ. Management was very friendly and check in was a breeze.

Reviewed on Jun 29, 2025

Cavendish Bosom Buddies Cottage Resort

Cavendish Bosom Buddies Cottage Resort

3 out of 5
Price was $1,277, price is now $1,167 per person
$1,167
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Colorado Springs (COS) to Charlottetown (YYG)
9.6/10 Exceptional! (87 reviews)
Wonderful spot. Nice an relaxing

Reviewed on Aug 18, 2025

The Great George

The Great George

5 out of 5
Downtown Charlottetown
Price was $1,208, price is now $1,108 per person
$1,108
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Colorado Springs (COS) to Charlottetown (YYG)
9.8/10 Exceptional! (1,010 reviews)
Bed was comfortable but the pillows were not as comfortable. The included continental breakfast was awesome with quality food and excellent selection. All the staff encountered were very friendly, helpful and professional.

Reviewed on Aug 18, 2025

Fairholm Boutique Inns

Fairholm Boutique Inns

5 out of 5
Downtown Charlottetown
Price was $1,171, price is now $1,087 per person
$1,087
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Colorado Springs (COS) to Charlottetown (YYG)
9.2/10 Wonderful! (580 reviews)
Wonderful, clean, historic, safe, fantastic breakfast

Reviewed on Aug 11, 2025

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Discover the most popular places to visit in O'Leary

Prince Edward Island Potato Museum

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.

Prince Edward Island Potato Museum

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
$162 nightly
The price is $187 total per night from Aug 31 to Sep 1
$187 total
Aug 31 - Sep 1
Total includes taxes and fees
8.4/10 Very Good! (713 reviews)
"Beautiful golf course with all the amenities you could ask for. Some issues inside, with dripping airco on the Scandi easy chairs in the lounge. There also was a space with a coffee vending machine for guests and a cute little coffee cup symbol outside. A note on the machine said it was broken, and ..."

Reviewed on Aug 16, 2025

Mill River Resort
Sunset View

Sunset View

Coleman
$268 nightly
The price is $308 total per night from Aug 26 to Aug 27
$308 total
Aug 26 - Aug 27
Total includes taxes and fees
8/10 Very Good! (3 reviews)
"Nice vintage olde farm house. Bed was comfortable and bathroom yet small is clean and does its job. Very quiet road with 5 mins walk to beach across the road. Wifi is great and quick. Wish it had a bbq for cooking and a smart tv for down time"

Reviewed on Aug 4, 2025

Sunset View
Family Friendly Cottage with Waterfront Access in beautiful Tyne Valley

Family Friendly Cottage with Waterfront Access in beautiful Tyne Valley

Tyne Valley
$259 nightly
The price is $297 total per night from Sep 19 to Sep 20
$297 total
Sep 19 - Sep 20
Total includes taxes and fees
9.8/10 Exceptional! (27 reviews)
"Well appointed cottage!"

Reviewed on Aug 15, 2025

Family Friendly Cottage with Waterfront Access in beautiful Tyne Valley
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.

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Frequently asked questions

How much does an O'Leary vacation package cost?
You can pick up a vacation package to this popular destination from $1,073 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.