O'Leary Vacations from $1,310
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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.
The Harbour House
Downtown Charlottetown
Price was $1,386, price is now $1,310 per person
$1,310
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Charlottetown (YYG)
9.4/10 Exceptional! (1,000 reviews)
Room was clean, cozy, and had a small fridge. There’s a “shared kitchen” that was listed but it’s really just access to a microwave. Breakfast was sufficient and had healthy options. Staff was lovely. Great location for walking to dinner etc. Property had a washer and dryer for guest to use- very helpful
Reviewed on Nov 8, 2025
The Hotel on Pownal
Downtown Charlottetown
Price was $1,537, price is now $1,424 per person
$1,424
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Charlottetown (YYG)
8.6/10 Excellent! (1,002 reviews)
The front desk staff people are very courteous and friendly. The room was very comfortable and clean.We liked the bath accessories provided and the towels were thick and white.
It was an extra bonus to have the delicious breakfast included.We opted to be "greener" and not have the housekeeping after the first night. We recieved a $10.00 gift card for doing this.We spent it at the Merchantman Bar :-)
Reviewed on Jan 18, 2026
The Sydney Boutique Inn
Downtown Charlottetown
Price was $1,531, price is now $1,458 per person
$1,458
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Charlottetown (YYG)
9.8/10 Exceptional! (1,005 reviews)
The breakfast was fresh, the room was beautiful. The rainfall shower was wonderful. Such comfy beds with feather duvets.
Reviewed on Jan 10, 2026
The Great George
Downtown Charlottetown
Price was $1,487, price is now $1,423 per person
$1,423
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Charlottetown (YYG)
9.6/10 Exceptional! (1,001 reviews)
Always a great place to stay in Charlottetown and love the location, rooms and of course the amazing breakfast!
Reviewed on Jan 13, 2026
Discover the most popular places to visit in O'Leary
Prince Edward Island Potato Museum
5/5(3 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.
O'Leary Hotel Deals
Mill River Resort
180 Mill River Resort Road, Route 136 Woodstock PE
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $141 total per night from Jan 25 to Jan 26
$141 total
Jan 25 - Jan 26
Total with taxes and fees
8.6/10 Excellent! (765 reviews)
Great service!
Reviewed on Jan 14, 2026
Crooked Cottage on Kildare Capes
Tignish PE
9.6/10 Exceptional! (39 reviews)
A wonderful piece of heaven—so quiet and relaxing. All the amenities anyone could ask for. We enjoyed a delicious homemade lobster dinner because everything was provided that we’d need. Will definitely come back to stay!
Reviewed on Oct 7, 2025
Riverside Landing Cottage
Alberton PE
10/10 Exceptional! (4 reviews)
New and clean, nice location, big hot tub, kayaks were fun, lovely deck right at the riverside.
Reviewed on Sep 5, 2025
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 |
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Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
