Title: O'Leary Vacation Packages & Trips 2026 from CA $1,235 | 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 $1,235

per person

Feb 13 - Feb 20

found 16 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Charlottetown (YYG)

8.6/10 Excellent! (1,002 reviews)

Clean rooms, easy access to rooms and parking

Reviewed on Jan 2, 2026

![Fairholm Boutique Inns](https://images.trvl-media.com/lodging/7000000/6810000/6810000/6809938/497e5058_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Fairholm Boutique Inns

Downtown Charlottetown

CA $1,377

per person

Feb 13 - Feb 20

found 16 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Charlottetown (YYG)

9.2/10 Wonderful! (613 reviews)

What a beautiful place to stay in Charlottetown! Lovely historic inn on a quiet street but within a short walking distance to shops, restaurants and the waterfront. The staff were exceptional and went above and beyond. The breakfast was delicious. I would highly recommend the Fairholm Boutique Inn.

Reviewed on Oct 25, 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 $1,246

per person

Feb 13 - Feb 20

found 16 hours ago

Roundtrip non-stop flight included

Calgary (YYC) 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 Great George](https://images.trvl-media.com/lodging/1000000/80000/74700/74682/ee970ccc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Great George

Downtown Charlottetown

CA $1,490

per person

Feb 13 - Feb 20

found 16 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Charlottetown (YYG)

9.6/10 Exceptional! (1,001 reviews)

The Great George has been one of our favourite places to stay in Charlottetown. The rooms and common areas are warm, clean, and stylish. The staff is friendly and attentive, The location is central to the shops, restaurants, and events. We highly recommend it.

Reviewed on Jan 4, 2026

![The Holman Grand Hotel](https://images.trvl-media.com/lodging/5000000/4360000/4359100/4359063/fb8150e9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Holman Grand Hotel

Downtown Charlottetown

CA $1,575

per person

Feb 13 - Feb 20

found 16 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Charlottetown (YYG)

9.4/10 Exceptional! (1,004 reviews)

Everything was great.

Reviewed on Jan 3, 2026

## 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

Jan 8 - Jan 9

includes taxes & fees

8.6/10 Excellent! (763 reviews)

Everything was perfect! The staff were all friendly.

Reviewed on Nov 16, 2025

[](https://expedia.ca/Hotel-Search?startDate=08%2F01%2F2026&endDate=09%2F01%2F2026&selected=28635&PinnedHotelID=28635&HadPinnedHotel=true&regionId=59292)

![Crooked Cottage on Kildare Capes](https://images.trvl-media.com/lodging/49000000/48310000/48308800/48308787/cce67b8d_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

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

[Get rates](https://expedia.ca/Hotel-Search?startDate=21%2F01%2F2026&endDate=22%2F01%2F2026&selected=48308787&PinnedHotelID=48308787&HadPinnedHotel=true&regionId=59292)

[](https://expedia.ca/Hotel-Search?startDate=21%2F01%2F2026&endDate=22%2F01%2F2026&selected=48308787&PinnedHotelID=48308787&HadPinnedHotel=true&regionId=59292)

![Beach, Oceanfront, 3 Bedroom](https://images.trvl-media.com/lodging/84000000/83610000/83604100/83604060/26aaac1c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Beach, Oceanfront, 3 Bedroom

 Saint Felix PE

8.6/10 Excellent! (9 reviews)

The cottage was beautiful and the pictures online didn't do it justice. Everything you needed for the week was provided, you just need to bring your personal items and food. The beach was beautiful, and waking up to the view and sound of the ocean was amazing!

Reviewed on Aug 25, 2025

[Get rates](https://expedia.ca/Hotel-Search?startDate=21%2F01%2F2026&endDate=22%2F01%2F2026&selected=83604060&PinnedHotelID=83604060&HadPinnedHotel=true&regionId=59292)

[](https://expedia.ca/Hotel-Search?startDate=21%2F01%2F2026&endDate=22%2F01%2F2026&selected=83604060&PinnedHotelID=83604060&HadPinnedHotel=true&regionId=59292)

[See all 52 properties in O'Leary](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F01%2F2026&endDate=09%2F01%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

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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- [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)
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- [Cedar Dunes Provincial Park ](https://www.expedia.ca/Cedar-Dunes-Provincial-Park-West-Point.d553248621562270806.Vacation-Attraction)
- [County Fair Mall ](https://www.expedia.ca/County-Fair-Mall-Summerside.d553248634270668549.Vacation-Attraction)
- [Darnley Greens Golf Course ](https://www.expedia.ca/Darnley-Greens-Golf-Course-Darnley.d553248621562270903.Vacation-Attraction)
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- [North Cape Lighthouse ](https://www.expedia.ca/North-Cape-Lighthouse-Seacow-Pond.d553248621573139875.Vacation-Attraction)
- [Prince Edward Island Potato Museum ](https://www.expedia.ca/Prince-Edward-Island-Potato-Museum-OLeary.d6300361.Vacation-Attraction)
- [Prince Edward Island Sports Hall of Fame and Museum ](https://www.expedia.ca/Prince-Edward-Island-Sports-Hall-Of-Fame-And-Museum-Summerside.d6300392.Vacation-Attraction)
- [Visit Roseville ](https://www.expedia.ca/Roseville.dx553248635975875454)
- [Seacow Pond Vacations ](https://www.expedia.ca/Seacow-Pond.d6346680.Destination-Travel-Guides)
- [St. Simon and St. Jude Church ](https://www.expedia.ca/St-Simon-And-St-Jude-Church-Tignish.d6300397.Vacation-Attraction)
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- [Tyne Valley Vacations ](https://www.expedia.ca/Tyne-Valley.d6346685.Destination-Travel-Guides)
- [Union Corner Provincial Park ](https://www.expedia.ca/Union-Corner-Provincial-Park-Union-Corner.d627247566691790848.Vacation-Attraction)
- [West Point Lighthouse ](https://www.expedia.ca/West-Point-Lighthouse-West-Point.d553248621562270807.Vacation-Attraction)
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- [Visit West Point ](https://www.expedia.ca/West-Point.dx6346684)
- [Wyatt House Museum ](https://www.expedia.ca/Wyatt-House-Museum-Summerside.d6300380.Vacation-Attraction)
- [All inclusive Vacation Packages Lot 8 ](https://www.expedia.ca/lp/theme-vacations/all-inclusive-vacations/553248635740488486/Lot-8)

- [Auto Rent Rental Cars in Lot 8 ](https://www.expedia.ca/Auto-Rent-Car-Rentals-In-Lot-8.d553248635740488486-c1006.Car-Rental-Guide-Suppliers)
- [Autoclick Rental Cars in Lot 8 ](https://www.expedia.ca/AutoClick-Car-Rentals-In-Lot-8.d553248635740488486-c1095.Car-Rental-Guide-Suppliers)
- [Car rentals near Lot 8 ](https://www.expedia.ca/Car-Rentals-In-Lot-8.d553248635740488486.Car-Rental-Guide)
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- [Discount Quebec Rental Cars in Lot 8 ](https://www.expedia.ca/Discount-Quebec-Car-Rentals-In-Lot-8.d553248635740488486-c1137.Car-Rental-Guide-Suppliers)
- [First Car Rental Rental Cars in Lot 8 ](https://www.expedia.ca/First-Car-Rental-Car-Rentals-In-Lot-8.d553248635740488486-c1107.Car-Rental-Guide-Suppliers)
- [Flizzr Rental Cars in Lot 8 ](https://www.expedia.ca/Flizzr-Car-Rentals-In-Lot-8.d553248635740488486-c1098.Car-Rental-Guide-Suppliers)
- [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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