O'Leary Vacation Packages 2026 from $927

O'Leary flight + hotel vacation packages

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

Cavendish Bosom Buddies Cottage Resort

$927

per person

Sep 14 - Sep 20

found 15 hours 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.

The Hotel on Pownal

Downtown Charlottetown

$1,233

per person

Aug 24 - Aug 28

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Charlottetown Alexander B. Campbell Airport (YYG)

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center, conference center, and conference space. There's a 24-hour gym on site, and laundry facilities and concierge services are also offered.

Fairholm Boutique Inns

Downtown Charlottetown

$1,362

per person

Aug 24 - Aug 28

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Charlottetown Alexander B. Campbell Airport (YYG)

A bar/lounge and a garden are featured at this bed & breakfast, along with free self parking. WiFi in public areas is free. A library, luggage storage, and concierge services are also on offer.

Rodd Charlottetown

Downtown Charlottetown

$1,273

per person

Aug 24 - Aug 28

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Charlottetown Alexander B. Campbell Airport (YYG)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling for business? Take advantage of the free WiFi in public areas, laundry service, and conference space. Enjoy the gym and perks like free self parking.

Dreamweavers Cottages and Vacation Homes

$964

per person

Sep 14 - Sep 20

found 15 hours 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.

Top O'Leary hotels deals

Mill River Resort

180 Mill River Resort Road, Route 136 Woodstock PE

Free Cancellation

Reserve now, pay when you stay

$202 nightly

$232 total

Jul 3 - Jul 4

Total with taxes and fees

This smoke-free hotel features a golf course, a full-service spa, and a restaurant. Enjoy the indoor pool and perks like free self parking and free WiFi. You'll appreciate the gym, bar/lounge, and laundry facilities.

BH Beach House

Saint Louis PE

Get rates

This vacation home features laundry facilities.

Foley’s Harbour House

Alberton PE

$365 nightly

$419 total

Jul 11 - Jul 12

Total with taxes and fees

This vacation home features a garden, laundry facilities, and barbecue grills.

Ocean Privacy on a secluded beachfront cottage on 16 acres of land!!!

Coleman PE

Get rates

This cottage features a garden, laundry facilities, and barbecue grills.

Beachfront, sandbar, 8p sauna, pickleball court, 6BR, outdoor kitchen and more

Wellington PE

Get rates

A sauna is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.

Sunset View

Coleman PE

$262 nightly

$301 total

Jul 5 - Jul 6

Total with taxes and fees

Stay at this vacation home in Hebron. Popular attractions Prince Edward Island Potato Museum and Cedar Dunes Provincial Park are located nearby.

Don't see what you're looking for?

See all available properties in O'Leary

View all properties

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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.

See properties

Frequently asked questions

How much are vacation packages to O'Leary?

You might be pleasantly surprised — you can vacation in O'Leary for only $927. 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.