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.
Loyalist Country Inn & Conference Centre
per person
Jun 16 - Jun 20
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.
Sunflower Guest Suites
per person
Jul 22 - Jul 29
found 7 hours ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
Green Gables Bungalow Court
per person
Jul 22 - Jul 29
found 7 hours ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
The Hotel on Pownal
per person
Jul 22 - Jul 29
found 7 hours ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
Microtel Inn & Suites by Wyndham Summerside
per person
Jul 22 - Jul 29
found 7 hours ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
Days Inn & Suites by Wyndham Summerside
per person
Jul 22 - Jul 29
found 7 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Charlottetown (YYG)
Book a stay at this business-friendly hotel in Summerside. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions International Fox Museum and Hall of Fame and Prince Edward Island Sports Hall of Fame and Museum are located nearby.
Andy's Blue House
per person
Jun 23 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottetown (YYG)
Stay at this 3-star guesthouse in Charlottetown. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions St. James Presbyterian Church and Beaconsfield Historic House are located nearby.
Anne Shirley Motel & Cottages
per person
Jul 22 - Jul 29
found 7 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Charlottetown (YYG)
Book a stay at this family-friendly motel 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 Site of Lucy Maud Montgomery's Cavendish Home 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.
Tue, Jun 3 - Fri, Jun 6
YYZ
Pearson Intl.
YYG
Charlottetown
$273 Roundtrip, found 1 day ago
$273
Roundtrip
found 1 day ago
Tue, Jun 3 - Fri, Jun 6
YYZ
Pearson Intl.
YYG
Charlottetown
$306 Roundtrip, found 1 day ago
$306
Roundtrip
found 1 day ago
Tue, Jun 3 - Fri, Jun 6
YYZ
Pearson Intl.
YYG
Charlottetown
$315 Roundtrip, found 1 day ago
$315
Roundtrip
found 1 day ago
Mon, May 26 - Fri, May 30
BOS
Logan Intl.
YYG
Charlottetown
$566 Roundtrip, found 6 days ago
$566
Roundtrip
found 6 days ago
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