O'Leary Vacations from $1,240
Book a Hotel + Flight or Car together to unlock savings
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 Hotel on Pownal
Downtown Charlottetown
Price was $1,497, price is now $1,240 per person
$1,240
per person
Sep 25 - Sep 29
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Charlottetown Alexander B. Campbell Airport (YYG)
8.8/10 Excellent! (1,010 reviews)
Liked the location -close to the downtown area -all within walking distance. The breakfast could be improved upon, as it is advertised to go to 10am, but most food seemed to run out by 9:30 ish. Staff and cleanliness were excellent. Be aware there is no elevator - and it is a 2 story location. Request main floor if you have heavy luggage.
Reviewed on Jul 22, 2026
Blackbush Beach Resort
Price was $2,127, price is now $1,844 per person
$1,844
per person
Sep 6 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Charlottetown Alexander B. Campbell Airport (YYG)
9.6/10 Exceptional! (422 reviews)
We loved our stay at Blackbush Beach Resort/The Hotel Acadia! It’s a gorgeous resort with close access to a beautiful red sand beach with dunes and a trail. The staff is super friendly and helpful and the rooms are wonderfully decorated with big windows. We enjoyed all the nature and wildlife that Grand Tracadie had to offer, from the Ospreys to seeing a red fox! We can’t wait to come back.
Reviewed on Jul 22, 2026
The Great George
Downtown Charlottetown
Price was $1,616, price is now $1,429 per person
$1,429
per person
Sep 25 - Sep 29
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Charlottetown Alexander B. Campbell Airport (YYG)
9.6/10 Exceptional! (1,013 reviews)
We immediately felt welcomed and at-home in the hotel. Our room was very comfortable and made a wonderful home base for our trip to Charlottetown. Everything was an easy walk from the hotel, which made exploring fun and stress-free. Would absolutely stay at the Great George Hotel again!
Reviewed on Jul 23, 2026
The Holman Grand Hotel
Downtown Charlottetown
Price was $1,913, price is now $1,715 per person
$1,715
per person
Sep 3 - Sep 8
found 5 hours ago
Roundtrip flight included
Burlington (BTV) to Charlottetown Alexander B. Campbell Airport (YYG)
9.4/10 Exceptional! (1,022 reviews)
Staff was very welcoming and accommodating
Reviewed on Jul 22, 2026
Stay near popular O'Leary attractions
O'Leary Hotel Deals
Mill River Resort
180 Mill River Resort Road, Route 136 Woodstock PE
Fully refundableReserve now, pay when you stay
$186 nightly
The price is $214 total per night from Jul 31 to Aug 1
$214 total
Jul 31 - Aug 1
Total with taxes and fees
8.6/10 Excellent! (815 reviews)
"Beautiful resort. Well updated. Clean. Staff at the front desk especially Cam"
Reviewed on Jul 20, 2026
Ocean Privacy on a secluded beachfront cottage on 16 acres of land!!!
Coleman PE
10/10 Exceptional! (1 review)
"A very private setting. The hosts were very easy to reach and helpful. We enjoyed our stay very much"
Reviewed on Jul 16, 2026
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
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.