O'Leary Vacation Packages 2026 from $954

O'Leary flight + hotel vacation packages

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

Multicultural Museum Cottages

$954

per person

Jul 1 - Jul 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Charlottetown (YYG)

This cottage features a terrace, barbecue grills, and free self parking. A garden and a picnic area are also provided.

The Hotel on Pownal

Downtown Charlottetown

$1,188

per person

Jul 1 - Jul 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Charlottetown (YYG)

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center, conference center, and conference space. There's a 24-hour gym on site, and laundry facilities and concierge services are also offered.

Pine Cottages

$1,036

per person

Jul 1 - Jul 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Charlottetown (YYG)

This cottage includes a garden and barbecue grills. Take advantage of the free self parking.

Rodd Charlottetown

Downtown Charlottetown

$1,198

per person

Jul 1 - Jul 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Charlottetown (YYG)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling for business? Take advantage of the free WiFi in public areas, laundry service, and conference space. Enjoy the gym and perks like free self parking.

By The Bay Cottages

$1,128

per person

Jul 1 - Jul 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Charlottetown (YYG)

A seasonal outdoor pool, free self parking, and laundry facilities are featured at this cottage. A picnic area, express check-in, and express check-out are also on offer.

Top O'Leary hotels deals

Mill River Resort

180 Mill River Resort Road, Route 136 Woodstock PE

Free Cancellation

Reserve now, pay when you stay

$150 nightly

$173 total

May 18 - May 19

Total with taxes and fees

This smoke-free hotel features a golf course, a full-service spa, and a restaurant. Enjoy the indoor pool and perks like free self parking and free WiFi. You'll appreciate the gym, bar/lounge, and laundry facilities.

The Little Yellow Farm House is country living, ocean views, open sky & bonfires

Chrysostome PE

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Stay at this farm stay in Saint Chrysostome. Enjoy air conditioning.

Oceanfront PEI Home with Ocean Views, Wraparound Deck & Private Beach

Coleman PE

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This cottage featured laundry facilities and barbecue grills.

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

Coleman PE

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This cottage features a garden, laundry facilities, and barbecue grills.

Riverside Landing Cottage

Alberton PE

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A hot tub is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.

BH Beach House

Saint Louis PE

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This vacation home features laundry facilities.

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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.

Popular places to visit

Prince Edward Island Potato Museum

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.

Frequently asked questions

How much are vacation packages to O'Leary?

You might be pleasantly surprised — you can vacation in O'Leary for only $954. Allow Travelocity to save you money and hassle with our excellent vacation packages. With hotels, flights and tours all in one place, why wait any longer?

Where can I get the best vacation package deals for O'Leary?

For the perfect O'Leary package deal, no one compares to Travelocity. Take your pick of 400 airlines and 1,000,000 properties across the globe to create the ultimate escape — it's really that simple.

Why should I purchase my O'Leary vacation package via Travelocity?

Savings, support and a stress-free booking are just the tip of the iceberg. Collect lifelong memories and enjoy a fulfilling travel experience knowing you can rely on 24/7 customer support. With the Travelocity Price Match Guarantee, you know you're getting the best deal available.

Can I save money on my O'Leary car rental if I combine it with hotels and flights?

Bundling your bookings into an O'Leary vacation package will save you a handsome sum. Bundle a flight and car; a flight, car and hotel; or a car and hotel. There's no better way to explore the greater O'Leary region than with your own rental car. You can also add experiences and activities to your Travelocity package.