O'Leary Vacation Packages 2026 from $1,077

O'Leary flight + hotel vacation packages

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

Traveller's Inn

$1,077

per person

Jun 17 - Jun 23

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Charlottetown (YYG)

A casino and an indoor pool are featured at this smoke-free hotel. Guests will appreciate free perks like free self parking and WiFi in public areas.

The Hotel on Pownal

Downtown Charlottetown

$1,607

per person

Jun 17 - Jun 23

found 1 day ago

Roundtrip flight included

Cleveland (CLE) 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.

Montgomery Cavendish Cottages

$1,374

per person

Jun 17 - Jun 23

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Charlottetown (YYG)

This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and barbecue grills are also provided.

Loyalist Country Inn & Conference Centre

$1,289

per person

Jun 17 - Jun 23

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Charlottetown (YYG)

This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy free perks like full breakfast and free self parking.

Multicultural Museum Cottages

$1,166

per person

Jun 17 - Jun 23

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Charlottetown (YYG)

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

Top O'Leary hotels deals

Mill River Resort

180 Mill River Resort Road, Route 136 Woodstock PE

$148 nightly

$170 total

Apr 3 - Apr 4

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.

Pool

Hot Tub

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.

Pet friendly

Air conditioning

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.

Kitchen

Washer

Large pet friendly retreat with tons of room for large groups.

Tignish PE

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A hot tub is featured at this lodge, along with laundry facilities and barbecue grills.

Hot Tub

Pet friendly

PEI Beach House on 14 acres

Cape Wolfe PE

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This vacation home features a garden, laundry facilities, and barbecue grills.

Kitchen

Washer

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.

Hot Tub

Kitchen

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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 $1,077. 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.