Title: O'Leary Vacation Packages & Trips 2026 from CA $527 | Expedia.ca [O'Leary Travel Guide](https://expedia.ca/OLeary.dx59292)[Hotels in O'Leary](https://expedia.ca/OLeary-Hotels.d59292.Travel-Guide-Hotels)[Vacation Rentals in O'Leary](https://expedia.ca/OLeary-Vacation-Rentals.d59292.Travel-Guide-VacationRentals)[Flights to O'Leary](https://expedia.ca/Cheap-Flights-To-OLeary.d59292.Travel-Guide-Flights)[O'Leary Car Rentals](https://expedia.ca/Car-Rentals-In-OLeary.d59292.Car-Rental-Guide) ![](https://images.trvl-media.com/place/553248635975866399/00dffd43-86e7-467c-9c99-fb37a0f01757.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # O'Leary Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by James Martin - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 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](https://www.expedia.ca/Mill-River-Golf-Course-Prince-Edward-Island.d6311500.Vacation-Attraction), [Prince Edward Island Potato Museum](https://www.expedia.ca/Prince-Edward-Island-Potato-Museum-Prince-Edward-Island.d6300361.Vacation-Attraction) and [Bloomfield Provincial Park](https://www.expedia.ca/Bloomfield-Provincial-Park-Prince-Edward-Island.d627230625342734336.Vacation-Attraction) 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. ## Top O'Leary Vacation Deals Price found within the past 48 hours. Click for updated prices. ![The Hotel on Pownal](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759011/ad0f52e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Hotel on Pownal Downtown Charlottetown CA $527 per person Jan 20 - Jan 27 found 1 day ago Roundtrip flight included Toronto (YTO) to Charlottetown (YYG) 8.6/10 Excellent! (1,002 reviews) Helpful and had all the info in the system Reviewed on Dec 13, 2025 ![Prince County Guest House](https://images.trvl-media.com/lodging/84000000/83140000/83130700/83130654/f06c914e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Prince County Guest House CA $560 per person Jan 20 - Jan 27 found 1 day ago Roundtrip flight included Toronto (YTO) to Charlottetown (YYG) 9/10 Wonderful! (205 reviews) Clean place, quaint and owners were great. Reviewed on Oct 18, 2025 ![The Harbour House](https://images.trvl-media.com/lodging/2000000/1200000/1197600/1197590/a3366ac1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Harbour House Downtown Charlottetown CA $576 per person Jan 20 - Jan 27 found 1 day ago Roundtrip flight included Toronto (YTO) 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 ![Loyalist Country Inn & Conference Centre](https://images.trvl-media.com/lodging/1000000/130000/126100/126093/60566f4a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Loyalist Country Inn & Conference Centre CA $571 per person Jan 20 - Jan 27 found 1 day ago Roundtrip flight included Toronto (YTO) to Charlottetown (YYG) 8.4/10 Very Good! (1,351 reviews) What a nice stay! The hotel is well maintained and decorated for the holidays. Everyone is kind. The rooms are large and beautiful. Ours had a view of the harbour. This exceeded our expectations. Thank you. Reviewed on Dec 11, 2025 ![The Sydney Boutique Inn](https://images.trvl-media.com/lodging/19000000/18470000/18462900/18462841/32970654_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Sydney Boutique Inn Downtown Charlottetown CA $671 per person Jan 20 - Jan 27 found 1 day ago Roundtrip flight included Toronto (YTO) to Charlottetown (YYG) 9.8/10 Exceptional! (1,005 reviews) Always a nice place to stay. The breakfast is incredible. The manager, Gordon, is a wonderful host. Highly recommend! Reviewed on Dec 6, 2025 ## Ready to book your vacation to O'Leary? Choose your dates ## O'Leary Hotel Deals ![Mill River Resort](https://images.trvl-media.com/lodging/1000000/30000/28700/28635/13ff5671_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Mill River Resort 180 Mill River Resort Road, Route 136 Woodstock PE Fully refundableReserve now, pay when you stay CA $199 CA $229 total Dec 18 - Dec 19 includes taxes & fees 8.4/10 Very Good! (761 reviews) Everything was perfect! The staff were all friendly. Reviewed on Nov 16, 2025 [](https://expedia.ca/Hotel-Search?startDate=18%2F12%2F2025&endDate=19%2F12%2F2025&selected=28635&PinnedHotelID=28635&HadPinnedHotel=true®ionId=59292) ![ Ocean Privacy on a secluded beachfront cottage on 16 acres of land!!!](https://images.trvl-media.com/lodging/122000000/121130000/121122600/121122504/17f91c92_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Ocean Privacy on a secluded beachfront cottage on 16 acres of land!!! Coleman PE [Get rates](https://expedia.ca/Hotel-Search?startDate=31%2F12%2F2025&endDate=01%2F01%2F2026&selected=121122504&PinnedHotelID=121122504&HadPinnedHotel=true®ionId=59292) [](https://expedia.ca/Hotel-Search?startDate=31%2F12%2F2025&endDate=01%2F01%2F2026&selected=121122504&PinnedHotelID=121122504&HadPinnedHotel=true®ionId=59292) ![The Little Yellow Farm House is country living, ocean views, open sky & bonfires](https://images.trvl-media.com/lodging/92000000/91750000/91746000/91745947/f2f2b9a0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Little Yellow Farm House is country living, ocean views, open sky & bonfires Chrysostome PE [Get rates](https://expedia.ca/Hotel-Search?startDate=31%2F12%2F2025&endDate=01%2F01%2F2026&selected=91745947&PinnedHotelID=91745947&HadPinnedHotel=true®ionId=59292) [](https://expedia.ca/Hotel-Search?startDate=31%2F12%2F2025&endDate=01%2F01%2F2026&selected=91745947&PinnedHotelID=91745947&HadPinnedHotel=true®ionId=59292) [See all 50 properties in O'Leary](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=18%2F12%2F2025&endDate=19%2F12%2F2025®ionId=59292) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### 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. [](https://expedia.ca/Prince-Edward-Island-Potato-Museum-OLeary.d6300361.Vacation-Attraction) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - [Bloomfield Hotels ](https://www.expedia.ca/Bloomfield-Hotels.d553248635975864540.Travel-Guide-Hotels) - [Hotels near Bloomfield Provincial Park ](https://www.expedia.ca/Bloomfield-Provincial-Park-Hotels.0-l627230625342734336-0.Travel-Guide-Filter-Hotels) - [Resorts in Bloomfield ](https://www.expedia.ca/Bloomfield-Resort-Hotels.d553248635975864540-aaResortHotels.Travel-Guide-Accommodation) - [Brae Hotels ](https://www.expedia.ca/Brae-Hotels.d553248635851305213.Travel-Guide-Hotels) - [Chalets in Cape Wolfe ](https://www.expedia.ca/Cape-Wolfe-Chalets.d553248635975866399-aaChalets.Travel-Guide-Accommodation) - [Cheap Hotels in Cape Wolfe ](https://www.expedia.ca/Cape-Wolfe-Hotels-Cheap-Hotels.0-0-d553248635975866399-tCheapHotels.Travel-Guide-Filter-Hotels) - [Cape Wolfe Hotels ](https://www.expedia.ca/Cape-Wolfe-Hotels.d553248635975866399.Travel-Guide-Hotels) - 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