Search Deals onO'Leary Vacation Packages
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O'Leary Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Sunflower Guest Suites
per person
Aug 10 - Aug 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Charlottetown (YYG)
Stay at this 3-star B&B in Summerside. Enjoy free parking, free bicycles on site, and onsite spa services. Our guests praise the helpful staff in our reviews. Popular attractions Summerside Range Lighthouse Rear and Bishop's Machine Shop Museum are located nearby.

By The Bay Cottages
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Charlottetown (YYG)
Stay at this 3-star cottage in Stanhope. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Heather Hannon Island Art Gallery and Stanhope Golf Club are located nearby.

Avonlea Forest Hill Cottages
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Charlottetown (YYG)
Stay at this 3-star cottage in Cavendish. Enjoy free WiFi, free parking, and a garden. Popular attractions Cavendish Beach and Forest Hills Golf Course are located nearby.

Fairholm Boutique Inns
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Charlottetown (YYG)
Stay at this 5-star luxury B&B in Charlottetown. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions The Mack and Province House National Historic Site of Canada are located nearby.

Jake & Jo's Cottages
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Charlottetown (YYG)
Stay at this 3-star family-friendly cottage in Brackley Beach. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions The Great Canadian Soap Company and Brackley Drive In are located nearby.

The Hotel on Pownal
per person
Aug 10 - Aug 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Charlottetown (YYG)
Book a stay at this business-friendly hotel in Charlottetown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions St. Peter's Anglican Cathedral and Confederation Centre of the Arts are located nearby.

Green Gables Bungalow Court
per person
Aug 10 - Aug 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Charlottetown (YYG)
Stay at this 3-star family-friendly cottage in Cavendish. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Cavendish Beach and Green Gables Heritage Place are located nearby.

Microtel Inn & Suites by Wyndham Summerside
per person
Aug 10 - Aug 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Charlottetown (YYG)
Stay at this 3-star family-friendly hotel in Summerside. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Credit Union Place and Red Shores Racetrack and Casino are located nearby.
O'Leary Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.



Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, Jul 9 - Mon, Jul 14
YYZ
Pearson Intl.
YYG
Charlottetown
$301 Roundtrip, found 4 hours ago
$301
Roundtrip
found 4 hours ago

Tue, Jul 15 - Wed, Jul 23
YOW
Macdonald-Cartier Intl.
YYG
Charlottetown
$366 Roundtrip, found 4 days ago
$366
Roundtrip
found 4 days ago

Wed, Oct 8 - Sat, Oct 18
BOS
Logan Intl.
YYG
Charlottetown
$441 Roundtrip, just found
$441
Roundtrip
just found

Wed, Sep 3 - Fri, Sep 12
YEG
Edmonton Intl.
YYG
Charlottetown
$460 Roundtrip, found 17 hours ago
$460
Roundtrip
found 17 hours ago
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