O'Leary Vacation Packages 2026 from $688

O'Leary flight + hotel vacation packages

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

Green Gables Bungalow Court

$688

per person

Sep 14 - Sep 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Charlottetown Alexander B. Campbell Airport (YYG)

This cottage features a seasonal outdoor pool and a rooftop terrace. Bring the family and enjoy the children's pool, playground, and arcade/game room. Guests will appreciate free perks like free self parking and WiFi in public areas.

Cavendish Bosom Buddies Cottage Resort

$927

per person

Sep 14 - Sep 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Charlottetown Alexander B. Campbell Airport (YYG)

This cottage features a seasonal outdoor pool and a hot tub. There's fun for all ages with a free kid's club and a playground, and barbecue grills are available on site. Enjoy the sauna and perks like free self parking.

Dreamweavers Cottages and Vacation Homes

$964

per person

Sep 14 - Sep 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Charlottetown Alexander B. Campbell Airport (YYG)

This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. Families will appreciate the playground and onsite laundry facilities. There's an outdoor pool on site, and a terrace and a picnic area are also provided.

Wild Pines Cabins

$716

per person

Sep 14 - Sep 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Charlottetown Alexander B. Campbell Airport (YYG)

This cabin doesn't skimp on freebies - guests receive free WiFi and free self parking. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the picnic area. There's a seasonal outdoor pool on site, and barbecue grills and a virtual front desk are also offered.

By The Bay Cottages

$719

per person

Sep 14 - Sep 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Charlottetown Alexander B. Campbell Airport (YYG)

A seasonal outdoor pool, free self parking, and laundry facilities are featured at this cottage. A picnic area, express check-in, and express check-out are also on offer.

Stay near popular O'Leary attractions

Prince Edward Island Potato Museum

9.0/10 (26 reviews)

You can spend an afternoon browsing the exhibits at Prince Edward Island Potato Museum during your travels in O'Leary. Discover the restaurants in this family-friendly area, or seek out the golf courses.

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Frequently asked questions

How much are vacation packages to O'Leary?

You might be pleasantly surprised — you can vacation in O'Leary for only $688. Allow Travelocity to save you money and hassle with our excellent vacation packages. With hotels, flights and tours all in one place, why wait any longer?

Where can I get the best vacation package deals for O'Leary?

For the perfect O'Leary package deal, no one compares to Travelocity. Take your pick of 400 airlines and 1,000,000 properties across the globe to create the ultimate escape — it's really that simple.

Why should I purchase my O'Leary vacation package via Travelocity?

Savings, support and a stress-free booking are just the tip of the iceberg. Collect lifelong memories and enjoy a fulfilling travel experience knowing you can rely on 24/7 customer support. With the Travelocity Price Match Guarantee, you know you're getting the best deal available.

Can I save money on my O'Leary car rental if I combine it with hotels and flights?

Bundling your bookings into an O'Leary vacation package will save you a handsome sum. Bundle a flight and car; a flight, car and hotel; or a car and hotel. There's no better way to explore the greater O'Leary region than with your own rental car. You can also add experiences and activities to your Travelocity package.