O'Leary Vacations from $877

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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.
Fair Isle Motel

Fair Isle Motel

2.5 out of 5
Price was $1,101, price is now $877 per person
$877
per person
Nov 5 - Nov 9
found 16 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Charlottetown (YYG)
8.4/10 Very Good! (533 reviews)
Great motel - room well equipped. Only complaint would be to get new pillows. Staff friendly. Great location. Get top floor room if you don’t want to hear people above you.

Reviewed on Sep 29, 2025

The Great George

The Great George

5 out of 5
Downtown Charlottetown
Price was $1,247, price is now $932 per person
$932
per person
Nov 5 - Nov 9
found 16 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Charlottetown (YYG)
9.8/10 Exceptional! (1,017 reviews)
Great location for all the quality restaurants.

Reviewed on Oct 2, 2025

The Hotel on Pownal

The Hotel on Pownal

2.5 out of 5
Downtown Charlottetown
Price was $1,197, price is now $902 per person
$902
per person
Nov 5 - Nov 9
found 16 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Charlottetown (YYG)
8.8/10 Excellent! (1,010 reviews)
The room was comfortable and clean but I did find it quite loud. I was at the end of the hall and was woken up repeatedly by people coming in and out of the hallway.

Reviewed on Oct 2, 2025

Fairholm Boutique Inns

Fairholm Boutique Inns

5 out of 5
Downtown Charlottetown
Price was $1,252, price is now $986 per person
$986
per person
Nov 5 - Nov 9
found 16 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Charlottetown (YYG)
9.2/10 Wonderful! (594 reviews)
Great location and very comfortable place to stay. Would go there again.

Reviewed on Sep 28, 2025

Wild Pines Cabins

Wild Pines Cabins

2 out of 5
Price was $1,128, price is now $900 per person
$900
per person
Nov 5 - Nov 9
found 16 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Charlottetown (YYG)
9.8/10 Exceptional! (20 reviews)
What a lovely spot..

Reviewed on Aug 29, 2025

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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.

Prince Edward Island Potato Museum

O'Leary Hotel Deals

Mill River Resort

Mill River Resort

3.5 out of 5
180 Mill River Resort Road, Route 136, Woodstock, PE
Fully refundableReserve now, pay when you stay
8.4/10 Very Good! (750 reviews)
"Food was mediocre at best"

Reviewed on Sep 21, 2025

Get rates
Mill River Resort
Family Friendly Cottage with Waterfront Access in beautiful Tyne Valley

Family Friendly Cottage with Waterfront Access in beautiful Tyne Valley

Tyne Valley
$216 nightly
The price is $248 total per night from Oct 17 to Oct 18
$248 total
Oct 17 - Oct 18
Total with taxes and fees
9.6/10 Exceptional! (33 reviews)
"Cottage was great nice view"

Reviewed on Sep 11, 2025

Family Friendly Cottage with Waterfront Access in beautiful Tyne Valley
Private ocean-front cottage

Private ocean-front cottage

Tyne Valley
8.8/10 Excellent! (14 reviews)
"Worn and dated"

Reviewed on Jul 11, 2025

Get rates
Private ocean-front cottage
See all 48 properties in O'Leary
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.

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

How much does an O'Leary vacation package cost?
You can pick up a vacation package to this popular destination from $877 on Expedia. But how much your vacation to O'Leary costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to O'Leary?
You can generally find lower prices and greater availability in November, December and January. Explore our cheap O'Leary vacation packages and you could score some excellent off-season deals.
How many days is enough for O'Leary?
The ideal duration for your O'Leary vacation depends on what you'd like to do and see. Typically, a handful of days to a week will give you time to visit all the main sights and discover some hidden treasures along the way.
How to find the best O'Leary package deals?
Begin your search for an O'Leary package deal by entering your destination and preferred trip dates under our "Packages" tab. Then apply some filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal O'Leary package deal right away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your O'Leary adventure underway.
Is it cheaper to book an O'Leary vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and hotels separately. Better still, you can customize your O'Leary getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to O'Leary?
If you have your O'Leary travel dates locked in, book as early as you can to score some terrific deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are great for traveling on a whim.
Does Expedia offer Book Now, Pay Later O'Leary vacation packages?
Secure your perfect escape to O'Leary with help from our Book Now, Pay Later vacations. There's no need to save up or wait for the next payday — we've joined forces with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans let you split the cost over 3, 6 or 12 months. With no hidden or late payment fees, you can easily stay on budget and snap up bargains before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.