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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 Arts Hotel

The Arts Hotel

3 out of 5
Price was $1,081, price is now $960 per person
$960
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottetown Alexander B. Campbell Airport (YYG)
Stay at this hotel in Charlottetown. Enjoy free WiFi, a 24-hour front desk, and rainfall showerheads. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Historic Charlottetown Waterfront and Charlottetown Port are located nearby.
I would never recommend this place to anyone. It was clean but the the rooms were extremely small and not having a fridge in my room was a huge inconvenience

Reviewed on Sep 3, 2026

The Holman Grand Hotel

The Holman Grand Hotel

4 out of 5
Price was $1,188, price is now $1,034 per person
$1,034
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottetown Alexander B. Campbell Airport (YYG)
Book a stay at this spa hotel in Charlottetown. Enjoy free WiFi, a full-service spa, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Historic Charlottetown Waterfront and Charlottetown Port are located nearby.

The Hotel on Pownal

The Hotel on Pownal

2.5 out of 5
Price was $1,108, price is now $979 per person
$979
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottetown Alexander B. Campbell Airport (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 Historic Charlottetown Waterfront and Charlottetown Port are located nearby.

Fairholm Boutique Inns

Fairholm Boutique Inns

5 out of 5
Price was $1,287, price is now $1,148 per person
$1,148
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottetown Alexander B. Campbell Airport (YYG)
Book a stay at this 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 Historic Charlottetown Waterfront and The Mack are located nearby.
The front desk staff were amazing, kind and helpful, it was a quiet and relaxing room. Excellent!

Reviewed on Aug 31, 2026

The Cliffside Inn

The Cliffside Inn

3 out of 5
Price was $1,160, price is now $1,057 per person
$1,057
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottetown Alexander B. Campbell Airport (YYG)
Book a stay at this beach B&B in Little Sands. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Rossignol Estate Winery and Northumberland Provincial Park are located nearby.
Loin de tout

Reviewed on Aug 25, 2026

Cavendish Bosom Buddies Cottage Resort

Cavendish Bosom Buddies Cottage Resort

3 out of 5
Price was $1,145, price is now $1,050 per person
$1,050
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottetown Alexander B. Campbell Airport (YYG)
Book a stay at this family-friendly cottage in Cavendish. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Green Gables Heritage Place and Cavendish Beach are located nearby.
Great stay!

Reviewed on Sep 3, 2026

Blackbush Beach Resort

Blackbush Beach Resort

4.5 out of 5
Price was $1,136, price is now $1,051 per person
$1,051
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.

Lily's Garden

Lily's Garden

4 out of 5
Price was $1,043, price is now $969 per person
$969
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottetown Alexander B. Campbell Airport (YYG)
Book a stay at this business-friendly B&B in Charlottetown. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Historic Charlottetown Waterfront and Charlottetown Port are located nearby.
Upon arriving you walk into a very strong incense smell throughout the space and persisted throughout our stay. Guests who are sensitive to scents may find this uncomfortable as I did. Also, they require you to use the slippers provided (which I found to be unhygienic). The photos show they have laundry but they don’t. The space was clean enough but some areas could be improved (e.g., bathroom mat was very dirty as well as the area around the mat and base of the tub).

Reviewed on Sep 3, 2026

O'Leary Vacation Packages 3-4 Night Stays

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

The Arts Hotel

3 out of 5
Downtown Charlottetown
Price was $1,081, price is now $960 per person
$960
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottetown Alexander B. Campbell Airport (YYG)
The Holman Grand Hotel

The Holman Grand Hotel

4 out of 5
Downtown Charlottetown
Price was $1,188, price is now $1,034 per person
$1,034
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottetown Alexander B. Campbell Airport (YYG)
The Hotel on Pownal

The Hotel on Pownal

2.5 out of 5
Downtown Charlottetown
Price was $1,108, price is now $979 per person
$979
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottetown Alexander B. Campbell Airport (YYG)
Fairholm Boutique Inns

Fairholm Boutique Inns

5 out of 5
Downtown Charlottetown
Price was $1,287, price is now $1,148 per person
$1,148
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottetown Alexander B. Campbell Airport (YYG)

Top Flight Deals

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

Flair Airlines
Mon, Oct 19 - Tue, Oct 20
YYZ
Pearson Intl.
YYG
Charlottetown Alexander B. Campbell Airport
$299 Roundtrip, found 2 hours ago
$299
Roundtrip
found 2 hours ago
Select Flair Airlines flight, departing Mon, Oct 19 from Pearson Intl. to Charlottetown Alexander B. Campbell Airport, returning Tue, Oct 20, priced at $299 found 2 hours ago
Air Canada
Tue, Oct 13 - Mon, Oct 19
YYZ
Pearson Intl.
YYG
Charlottetown Alexander B. Campbell Airport
$364 Roundtrip, found 1 hour ago
$364
Roundtrip
found 1 hour ago
Select Air Canada flight, departing Tue, Oct 13 from Pearson Intl. to Charlottetown Alexander B. Campbell Airport, returning Mon, Oct 19, priced at $364 found 1 hour ago
Porter Airlines
Tue, Oct 13 - Mon, Oct 19
YYZ
Pearson Intl.
YYG
Charlottetown Alexander B. Campbell Airport
$407 Roundtrip, found 1 hour ago
$407
Roundtrip
found 1 hour ago
Select Porter Airlines flight, departing Tue, Oct 13 from Pearson Intl. to Charlottetown Alexander B. Campbell Airport, returning Mon, Oct 19, priced at $407 found 1 hour ago
Air Transat
Tue, Oct 13 - Mon, Oct 19
YYZ
Pearson Intl.
YYG
Charlottetown Alexander B. Campbell Airport
$413 Roundtrip, found 1 hour ago
$413
Roundtrip
found 1 hour ago
Select Air Transat flight, departing Tue, Oct 13 from Pearson Intl. to Charlottetown Alexander B. Campbell Airport, returning Mon, Oct 19, priced at $413 found 1 hour ago