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O'Leary Vacation Packages

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O'Leary Flight + Hotel Packages

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

The Harbour House

4 out of 5
Price was $1,186, price is now $1,126 per person
$1,126
per person
Nov 22 - Nov 30
found 8 hours ago
Roundtrip non-stop flight included
New York (NYC) to Charlottetown Alexander B. Campbell Airport (YYG)
Book a stay at this historic B&B in Charlottetown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Historic Charlottetown Waterfront and Charlottetown Port are located nearby.
Amazing breakfast

Reviewed on Oct 21, 2026

The Sydney Boutique Inn

The Sydney Boutique Inn

5 out of 5
Price was $1,387, price is now $1,312 per person
$1,312
per person
Nov 22 - Nov 30
found 8 hours ago
Roundtrip non-stop flight included
New York (NYC) to Charlottetown Alexander B. Campbell Airport (YYG)
Book a stay at this 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 Charlottetown Port and Historic Charlottetown Waterfront are located nearby.
Perfection! 3 nights of luxurious comfort! Wish we had stayed for a week.

Reviewed on Oct 22, 2026

Blackbush Beach Resort

Blackbush Beach Resort

4.5 out of 5
Price was $1,290, price is now $1,229 per person
$1,229
per person
Nov 22 - Nov 30
found 8 hours ago
Roundtrip non-stop flight included
New York (NYC) to Charlottetown Alexander B. Campbell Airport (YYG)
Book a stay at this luxury resort in Grand Tracadie. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Prince Edward Island National Park and Stanhope Golf Club are located nearby.
They had everything you could ever need for your stay plus more!! Hot tub, swim spa, sauna, yoga studio, huge bedrooms, heated bathroom floor, giant bath towels, I could go on and on! Will definitely be back during the summer season to take advantage of the beach

Reviewed on Oct 20, 2026

Top Flight Deals

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

Flair Airlines
Fri, Oct 23 - Sat, Nov 7
YYZ
Pearson Intl.
YYG
Charlottetown Alexander B. Campbell Airport
$422 Roundtrip, just found
$422
Roundtrip
just found
Select Flair Airlines flight, departing Fri, Oct 23 from Pearson Intl. to Charlottetown Alexander B. Campbell Airport, returning Sat, Nov 7, priced at $422 just found
Flair Airlines
Fri, Oct 23 - Thu, Nov 5
YYZ
Pearson Intl.
YYG
Charlottetown Alexander B. Campbell Airport
$444 Roundtrip, found 4 hours ago
$444
Roundtrip
found 4 hours ago
Select Flair Airlines flight, departing Fri, Oct 23 from Pearson Intl. to Charlottetown Alexander B. Campbell Airport, returning Thu, Nov 5, priced at $444 found 4 hours ago
Air Transat
Mon, Oct 26 - Mon, Nov 2
YOW
Macdonald-Cartier Intl.
YYG
Charlottetown Alexander B. Campbell Airport
$710 Roundtrip, found 20 hours ago
$710
Roundtrip
found 20 hours ago
Select Air Transat flight, departing Mon, Oct 26 from Macdonald-Cartier Intl. to Charlottetown Alexander B. Campbell Airport, returning Mon, Nov 2, priced at $710 found 20 hours ago
Air Canada
Thu, Jun 24 - Tue, Jun 29
BOS
Logan Intl.
YYG
Charlottetown Alexander B. Campbell Airport
$891 Roundtrip, just found
$891
Roundtrip
just found
Select Air Canada flight, departing Thu, Jun 24 from Logan Intl. to Charlottetown Alexander B. Campbell Airport, returning Tue, Jun 29, priced at $891 just found