Title: O'Leary Vacation Packages & Trips 2026 from CA $994 | 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/59292/69fe3f2b-c4bc-47c2-a657-33009f68af73.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# O'Leary Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

- ##  
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.

![Loyalist Country Inn & Conference Centre](https://images.trvl-media.com/lodging/1000000/130000/126100/126093/fc6c1b74_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Loyalist Country Inn & Conference Centre

CA $994

per person

Jun 21 - Jun 26

found 14 hours ago

Roundtrip flight included

Toronto (YTO) to Charlottetown (YYG)

8.4/10 Very Good! (1,380 reviews)

the view from my room was beautiful. Nice older motel. A bit outdated....could use some fresh paint... but overall a nice stay.

Reviewed on Mar 30, 2026

![The Hotel on Pownal](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759011/b6165cd1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Hotel on Pownal

Downtown Charlottetown

CA $1,058

per person

May 13 - May 18

found 12 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Charlottetown (YYG)

8.8/10 Excellent! (1,008 reviews)

They have complimentary beer and popcorn at happy hour. It's quite a surprise for us.

Reviewed on Mar 30, 2026

![The Great George](https://images.trvl-media.com/lodging/1000000/80000/74700/74682/0348390a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Great George

Downtown Charlottetown

CA $1,269

per person

May 13 - May 18

found 12 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Charlottetown (YYG)

9.6/10 Exceptional! (1,005 reviews)

The staff was welcoming and incredibly helpful when we had any questions. Loved the atmosphere of the property and the breakfast was simple but delicious! I also appreciated there being ample parking. Only con was there was no microwave in the room or in the main lobby which would have been useful.

Reviewed on Mar 31, 2026

![Comfort Inn](https://images.trvl-media.com/lodging/1000000/570000/563900/563863/cc32a81a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Comfort Inn

CA $1,052

per person

May 13 - May 18

found 12 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Charlottetown (YYG)

8.2/10 Very Good! (1,001 reviews)

Always polite and helpful staff!

Reviewed on Mar 22, 2026

![Skyline Terrace Cottages](https://images.trvl-media.com/lodging/107000000/106060000/106051700/106051647/812a4d4d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Skyline Terrace Cottages

CA $1,426

per person

Jun 20 - Jun 27

found 11 hours ago

Roundtrip flight included

Toronto (YYZ) to Charlottetown (YYG)

7.2/10 Good! (28 reviews)

Cottage was very clean and tidy. Great access to park and water.

Reviewed on Sep 23, 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

CA $229

CA $263 total

Apr 4 - Apr 5

includes taxes & fees

8.6/10 Excellent! (783 reviews)

Great winter experience with the family. Set the resort up well for the young kids!

Reviewed on Mar 22, 2026

[](https://expedia.ca/Hotel-Search?startDate=04%2F04%2F2026&endDate=05%2F04%2F2026&selected=28635&PinnedHotelID=28635&HadPinnedHotel=true&regionId=59292)

![The Little Yellow Farm House is country living, ocean views, open sky & bonfires](https://images.trvl-media.com/lodging/92000000/91750000/91746000/91745947/33130492_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=15%2F04%2F2026&endDate=16%2F04%2F2026&selected=91745947&PinnedHotelID=91745947&HadPinnedHotel=true&regionId=59292)

[](https://expedia.ca/Hotel-Search?startDate=15%2F04%2F2026&endDate=16%2F04%2F2026&selected=91745947&PinnedHotelID=91745947&HadPinnedHotel=true&regionId=59292)

![ Ocean Privacy on a secluded beachfront cottage on 16 acres of land!!!](https://images.trvl-media.com/lodging/122000000/121130000/121122600/121122504/64beb2b4_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=15%2F04%2F2026&endDate=16%2F04%2F2026&selected=121122504&PinnedHotelID=121122504&HadPinnedHotel=true&regionId=59292)

[](https://expedia.ca/Hotel-Search?startDate=15%2F04%2F2026&endDate=16%2F04%2F2026&selected=121122504&PinnedHotelID=121122504&HadPinnedHotel=true&regionId=59292)

[See all 53 properties in O'Leary](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=02%2F04%2F2026&endDate=03%2F04%2F2026&regionId=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

4.5/5(4 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. 

[](https://expedia.ca/Prince-Edward-Island-Potato-Museum-OLeary.d6300361.Vacation-Attraction)

## Explore a world of travel with Expedia

- Lodging
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- [All inclusive Vacation Packages Lot 8 ](https://www.expedia.ca/lp/theme-vacations/all-inclusive-vacations/553248635740488486/Lot-8)

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- [Autoclick Rental Cars in Lot 8 ](https://www.expedia.ca/AutoClick-Car-Rentals-In-Lot-8.d553248635740488486-c1095.Car-Rental-Guide-Suppliers)
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- [Foco Rental Cars in Lot 8 ](https://www.expedia.ca/Foco-Car-Rentals-In-Lot-8.d553248635740488486-c1111.Car-Rental-Guide-Suppliers)
- [Greenmotion Drive&Go Rental Cars in Lot 8 ](https://www.expedia.ca/GreenMotion-DriveGo-Car-Rentals-In-Lot-8.d553248635740488486-c1042.Car-Rental-Guide-Suppliers)
- [Leasys Rental Cars in Lot 8 ](https://www.expedia.ca/Leasys-Car-Rentals-In-Lot-8.d553248635740488486-c1099.Car-Rental-Guide-Suppliers)
- [Localiza Argentina Rental Cars in Lot 8 ](https://www.expedia.ca/Localiza-Argentina-Car-Rentals-In-Lot-8.d553248635740488486-c1097.Car-Rental-Guide-Suppliers)
- [Movida Rent A Car Rental Cars in Lot 8 ](https://www.expedia.ca/Movida-Rent-A-Car-Car-Rentals-In-Lot-8.d553248635740488486-c1083.Car-Rental-Guide-Suppliers)
- [Oryx Rent A Car Rental Cars in Lot 8 ](https://www.expedia.ca/ORYX-Rent-A-Car-Car-Rentals-In-Lot-8.d553248635740488486-c1059.Car-Rental-Guide-Suppliers)
- [Premium Car Rentals in Lot 8 ](https://www.expedia.ca/Premium-Car-Rentals-In-Lot-8.d553248635740488486-tPremium.Car-Rental-Guide-Class)
- [Sports Car Car Rentals in Lot 8 ](https://www.expedia.ca/Sportscar-Car-Rentals-In-Lot-8.d553248635740488486-tSportscar.Car-Rental-Guide-Class)
- [Turisprime Rental Cars in Lot 8 ](https://www.expedia.ca/Turisprime-Car-Rentals-In-Lot-8.d553248635740488486-c1100.Car-Rental-Guide-Suppliers)

- [Cape Wolfe Vacation Rentals ](https://www.expedia.ca/Cape-Wolfe-Vacation-Rentals.d553248635975866399.Travel-Guide-VacationRentals)
- [West Point Vacation Rentals ](https://www.expedia.ca/West-Point-Vacation-Rentals.d6346684.Travel-Guide-VacationRentals)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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