O'Leary Vacation Packages

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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.

Top O'Leary Vacation Deals

Price found within the past 48 hours. Click for updated prices.
St Lawrence Motel

St Lawrence Motel

2.5 out of 5
Price was CA $880, price is now CA $786 per person
CA $786
per person
Aug 25 - Aug 30
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Charlottetown Alexander B. Campbell Airport (YYG)
8.6/10 Excellent! (257 reviews)
Everything was great. No complaints. The owners were very nice. Would definitely stay here again. The grandkids loved the pool.

Reviewed on Jul 3, 2026

Microtel Inn & Suites by Wyndham Summerside

Microtel Inn & Suites by Wyndham Summerside

3 out of 5
Price was CA $1,589, price is now CA $1,346 per person
CA $1,346
per person
Aug 23 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Charlottetown Alexander B. Campbell Airport (YYG)
9.2/10 Wonderful! (619 reviews)
We liked the access to the pool and other facilities.

Reviewed on Jul 4, 2026

Rodd Charlottetown

Rodd Charlottetown

4.5 out of 5
Downtown Charlottetown
Price was CA $1,559, price is now CA $1,362 per person
CA $1,362
per person
Aug 25 - Aug 30
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Charlottetown Alexander B. Campbell Airport (YYG)
8.8/10 Excellent! (1,006 reviews)
The location of Rodd Charlottetown Hotel is excellent. We were able to walk to the bus tour pick up locations, walk to harbour front shops, Queen street shop. No need to rent a car. Pool was great and warm. The restaurant salads and children’s meals were very good and average price. Best cup of tea I had on the island and within walking location of two Cows ice cream shops. Also, within walking distance of confederation Plays.

Reviewed on Jul 3, 2026

Wood Duck Cottage

Wood Duck Cottage

3.5 out of 5
Price was CA $1,047, price is now CA $923 per person
CA $923
per person
Sep 7 - Sep 10
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Charlottetown Alexander B. Campbell Airport (YYG)
9.4/10 Exceptional! (11 reviews)
My family really enjoyed this cottage! Its very roomy, and close to everything. The cottage was very clean, modern, and felt like we were right at home! * Our only negative would be that the wifi was extremely slow so it was hard to connect the TV streaming services and use our phones. We will definitely be back! Our favorite spot we've stayed in cavendish yet!

Reviewed on Jun 21, 2026

Multicultural Museum Cottages

Multicultural Museum Cottages

3 out of 5
Price was CA $940, price is now CA $837 per person
CA $837
per person
Aug 25 - Aug 30
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Charlottetown Alexander B. Campbell Airport (YYG)
9/10 Wonderful! (50 reviews)
Good location, had lots of space for our group.

Reviewed on Jun 30, 2026

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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
The price is CA $319 per night from Jul 5 to Jul 6
CA $319
CA $367 total
Jul 5 - Jul 6
includes taxes & fees
8.6/10 Excellent! (802 reviews)
"The main complaint was that the air conditioning made the hotel very cold. The dining room and bar were uncomfortably cold. Outside it was 31 degrees and inside may be 17. Our room was extremely cold and we had to actually heat the room to make it comfortable. Our room was down to 64 F. The staff ..."

Reviewed on Jul 4, 2026

Mill River Resort
BH Beach House

BH Beach House

Saint Louis PE
9.8/10 Exceptional! (15 reviews)
"Beautiful beach house on a large property. The bedrooms are lovely and there is lots of areas for relaxing and playing games. The hot tub was great and there was plenty of outdoor seating. A quick walk down the back yard takes you to stairs to the beach which was sandy and quite private. A nice bonus ..."

Reviewed on Jun 29, 2026

Get rates
BH Beach House
Ocean Privacy on a secluded beachfront cottage on 16 acres of land!!!

Ocean Privacy on a secluded beachfront cottage on 16 acres of land!!!

Coleman PE
Get rates
Ocean Privacy on a secluded beachfront cottage on 16 acres of land!!!
See all 56 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.
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Stay near popular O'Leary attractions

Prince Edward Island Potato Museum

9.0/10 (26 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.
See properties

Frequently asked questions

How much does an O'Leary vacation package cost?
You'll find cheap prices from CA $786 on Expedia for your O'Leary break. However, a range of factors like the hotel choice, length of stay and season will determine how much your vacation to O'Leary costs.
What are the cheapest months to go to O'Leary?
January, February and November are great times to look for cheap O'Leary vacation packages. Opting to travel in less busy periods means you can typically find reduced prices on hotels and flights.
How many days is enough for O'Leary?
The ideal duration of your O'Leary vacation depends on what you'd like to see. Typically, a few days to a week will give you plenty of time to go to all the leading sights and explore some hidden treasures along the way.
How to find the best O'Leary package deals?
Landing a cheap O'Leary package deal is a cinch with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget range, add a few filters and browse what's available. You can fine-tune your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to view the most wallet-friendly O'Leary package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book an O'Leary vacation as a package?
You can enjoy significant savings on your next O'Leary getaway by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to browse the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to O'Leary?
If you're considering a spur-of-the-moment O'Leary getaway, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can find amazing deals on your hotels and flights by booking ahead.
How to plan a trip to O'Leary?

  1. Choose your travel dates: The things you plan to do in O'Leary and your preferred season can help you decide when to go.
  2. Budget wisely: As well as the cost of your stay, you'll need to consider other expenses too. These include food, flights and transportation. Also, put aside a little extra for unexpected costs that could arise during your trip to O'Leary.
  3. Decide how long to go for: Now that you're up to speed on O'Leary, you can figure out the ideal length of your break. Pull together a rough itinerary and give yourself enough time to cover everything you want to see.
  4. Bundle your accommodations and airfare: Once you've nailed down your travel dates and duration, lock in the right O'Leary vacation package for you.

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