Deals on vacations and trips to O'Leary

Save when you book O'Leary package deals

Choose two or more items and save on your trip:

O'Leary flight + hotel vacation packages

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

The Harbour House

4 out of 5
Downtown Charlottetown
Price was $726, price is now $645 per person
$645
per person
Mar 27 - Mar 30
found 11 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottetown (YYG)
This bed & breakfast doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. A terrace, a garden, and luggage storage are also on offer.
The Hotel on Pownal

The Hotel on Pownal

2.5 out of 5
Downtown Charlottetown
Price was $723, price is now $654 per person
$654
per person
Mar 27 - Mar 30
found 11 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottetown (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

Fairholm Boutique Inns

5 out of 5
Downtown Charlottetown
Price was $787, price is now $723 per person
$723
per person
Mar 27 - Mar 30
found 11 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottetown (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.
The Great George

The Great George

5 out of 5
Downtown Charlottetown
Price was $808, price is now $745 per person
$745
per person
Mar 27 - Mar 30
found 11 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottetown (YYG)
A full-service spa and a 24-hour gym are featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy free perks like on-the-go breakfast and free self parking.
The Dawson House Bed & Breakfast

The Dawson House Bed & Breakfast

4 out of 5
Price was $773, price is now $717 per person
$717
per person
Mar 27 - Mar 30
found 11 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottetown (YYG)
This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free local cuisine breakfast each morning. Luggage storage is also provided.

Top O'Leary hotels deals

Mill River Resort

Mill River Resort

3.5 out of 5
180 Mill River Resort Road, Route 136 Woodstock PE
Free Cancellation
Reserve now, pay when you stay
Get rates
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.
Pool
Hot Tub
Ocean Privacy on a secluded beachfront cottage on 16 acres of land!!!

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

2 out of 5
Coleman PE
Get rates
This cottage features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
The Little Yellow Farm House is country living, ocean views, open sky & bonfires

The Little Yellow Farm House is country living, ocean views, open sky & bonfires

Chrysostome PE
Get rates
Stay at this farm stay in Saint Chrysostome. Enjoy air conditioning.
Pet friendly
Air conditioning
Crooked Cottage on Kildare Capes

Crooked Cottage on Kildare Capes

Tignish PE
Get rates
This cottage features barbecue grills.
Kitchen
Pet friendly
Riverside Landing Cottage

Riverside Landing Cottage

Alberton PE
Get rates
A hot tub is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Hot Tub
Kitchen
Beach, Oceanfront, 3 Bedroom

Beach, Oceanfront, 3 Bedroom

Saint Felix PE
Get rates
This cottage features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
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.

Popular places to visit

Prince Edward Island Potato Museum

5/5(3 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.

Prince Edward Island Potato Museum

Frequently asked questions

How much are vacation packages to O'Leary?
You might be pleasantly surprised — you can vacation in O'Leary for only $645. 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.

Photos of local treasures

Browse O'Leary vacation photos for more inspiration

Photo by James Martin
Photo by James Martin

Explore More Ways to Travel with Travelocity