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
Jun 21 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Rodd Crowbush Golf & Beach Resort
per person
Jun 21 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottetown (YYG)
Stay at this 5-star luxury resort in West Saint Peters. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Rodd Crowbush Golf and Beach Resort and The Links at Crowbush Cove are located nearby.
Cavendish Bosom Buddies Cottage Resort
per person
Jun 21 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottetown (YYG)
Stay at this 3-star family-friendly cottage in Cavendish. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Cavendish Beach and Site of Lucy Maud Montgomery's Cavendish Home are located nearby.
Loyalist Country Inn & Conference Centre
per person
Jul 4 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottetown (YYG)
Stay at this 3.5-star business-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 Summerside Harbor and Eptek Art and Culture Centre are located nearby.
The Great George
per person
Jul 4 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottetown (YYG)
Stay at this 5-star luxury 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. Dunstan's Basilica and Gahan House are located nearby.
The Hotel on Pownal
per person
Jun 21 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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
Jun 21 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
St Lawrence Motel
per person
Jun 21 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottetown (YYG)
Stay at this motel in North Rustico. Enjoy free WiFi, free parking, and private pools. Our guests praise the helpful staff in our reviews. Popular attractions Watermark Theatre and North Rustico Beach are located nearby.
O'Leary Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
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.
Fri, Jun 13 - Mon, Jun 16
YYZ
Pearson Intl.
YYG
Charlottetown
$186 Roundtrip, found 3 days ago
$186
Roundtrip
found 3 days ago
Fri, Jun 13 - Mon, Jun 16
YYZ
Pearson Intl.
YYG
Charlottetown
$310 Roundtrip, found 3 days ago
$310
Roundtrip
found 3 days ago
Mon, May 26 - Fri, May 30
BOS
Logan Intl.
YYG
Charlottetown
$525 Roundtrip, found 4 hours ago
$525
Roundtrip
found 4 hours ago
Sat, May 3 - Mon, May 5
YOW
Macdonald-Cartier Intl.
YYG
Charlottetown
$711 Roundtrip, found 2 days ago
$711
Roundtrip
found 2 days ago
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