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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.
Lily's Garden

Lily's Garden

4 out of 5
Price was $674, price is now $635 per person
$635
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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.
Easy to find, very useful kitchen amenities, cute room, and very comfortable bed.

Reviewed on Jul 18, 2026

The Hotel on Pownal

The Hotel on Pownal

2.5 out of 5
Price was $1,174, price is now $939 per person
$939
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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.
Property was decent, room was passable. Staff was nice enough and lobby was nice. Really Good location to walk around Charlottetown

Reviewed on Jul 20, 2026

The Cliffside Inn

The Cliffside Inn

3 out of 5
Price was $929, price is now $807 per person
$807
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip 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.
Such a beautiful setting right on the water - peaceful and secluded. We were there just a night but really enjoyed the comfort and Amber’s kind hospitality.

Reviewed on Jul 18, 2026

Skyline Terrace Cottages

Skyline Terrace Cottages

3 out of 5
Price was $939, price is now $866 per person
$866
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Charlottetown Alexander B. Campbell Airport (YYG)
Stay at this country house in Stanhope. Enjoy free WiFi, free parking, and a garden. Popular attractions Prince Edward Island National Park and Heather Hannon Island Art Gallery are located nearby.
Need to make sure there is someone in the office that speaks English.

Reviewed on Jul 15, 2026

Avonlea Forest Hill Cottages

Avonlea Forest Hill Cottages

3 out of 5
Price was $1,406, price is now $1,300 per person
$1,300
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Charlottetown Alexander B. Campbell Airport (YYG)
Stay at this cottage in Cavendish. Enjoy free WiFi, free parking, and a garden. Popular attractions Cavendish Beach and Shining Waters Family Fun Park are located nearby.
Great stay!

Reviewed on Jul 16, 2026

Anne Shirley Motel & Cottages

Anne Shirley Motel & Cottages

2 out of 5
Price was $726, price is now $673 per person
$673
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Charlottetown Alexander B. Campbell Airport (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 Green Gables Heritage Place are located nearby.
Rooms very out dated. Trash all outside room on ground. Found earwigs on the floor by my bed in the morning. None of the plugs worked in the bathroom as well so you could not use the blower dryer they had. Thank god I took a hairdryer.

Reviewed on Jul 19, 2026

Rodd Crowbush Golf & Beach Resort

Rodd Crowbush Golf & Beach Resort

5 out of 5
Price was $1,046, price is now $977 per person
$977
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Charlottetown Alexander B. Campbell Airport (YYG)
Book a stay at this 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.
Beautiful beach and relaxing setting. Also, nice and close to the Greenwich Dunes Trail and Beach which made for a great day trip. Highly recommend opting for a cottage. Very spacey and everything we needed for our stay, including a huge backyard area with BBQ. Shuttles to the beach, although not a far walk was a nice touch.

Reviewed on Jul 18, 2026

Green Gables Bungalow Court

Green Gables Bungalow Court

3 out of 5
Price was $840, price is now $795 per person
$795
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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. Our guests praise the helpful staff in our reviews. Popular attractions Cavendish Beach and Green Gables Heritage Place are located nearby.
A+

Reviewed on Jul 19, 2026

O'Leary Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Cliffside Inn

The Cliffside Inn

3 out of 5
Price was $929, price is now $807 per person
$807
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip 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 $1,174, price is now $939 per person
$939
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Charlottetown Alexander B. Campbell Airport (YYG)
Skyline Terrace Cottages

Skyline Terrace Cottages

3 out of 5
Price was $939, price is now $866 per person
$866
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Charlottetown Alexander B. Campbell Airport (YYG)
Avonlea Forest Hill Cottages

Avonlea Forest Hill Cottages

3 out of 5
Price was $1,406, price is now $1,300 per person
$1,300
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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
Wed, Aug 5 - Wed, Aug 26
YYZ
Pearson Intl.
YYG
Charlottetown Alexander B. Campbell Airport
$283 Roundtrip, found 4 hours ago
$283
Roundtrip
found 4 hours ago
Select Flair Airlines flight, departing Wed, Aug 5 from Pearson Intl. to Charlottetown Alexander B. Campbell Airport, returning Wed, Aug 26, priced at $283 found 4 hours ago
Porter Airlines
Sat, Aug 8 - Fri, Aug 14
YHM
John C. Munro Hamilton Intl.
YYG
Charlottetown Alexander B. Campbell Airport
$370 Roundtrip, found 1 day ago
$370
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Sat, Aug 8 from John C. Munro Hamilton Intl. to Charlottetown Alexander B. Campbell Airport, returning Fri, Aug 14, priced at $370 found 1 day ago
Air Canada
Wed, Aug 5 - Mon, Aug 17
YKF
Region of Waterloo Intl.
YYG
Charlottetown Alexander B. Campbell Airport
$379 Roundtrip, found 1 day ago
$379
Roundtrip
found 1 day ago
Select Air Canada flight, departing Wed, Aug 5 from Region of Waterloo Intl. to Charlottetown Alexander B. Campbell Airport, returning Mon, Aug 17, priced at $379 found 1 day ago
Air Canada
Wed, Aug 5 - Mon, Aug 17
YTZ
Billy Bishop Toronto City
YYG
Charlottetown Alexander B. Campbell Airport
$388 Roundtrip, found 1 day ago
$388
Roundtrip
found 1 day ago
Select Air Canada flight, departing Wed, Aug 5 from Billy Bishop Toronto City to Charlottetown Alexander B. Campbell Airport, returning Mon, Aug 17, priced at $388 found 1 day ago