O'Leary Vacation Packages 2026 from $1,536

O'Leary flight + hotel vacation packages

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

Multicultural Museum Cottages

$1,536

per person

Jun 28 - Jul 4

found 1 day ago

Roundtrip non-stop flight included

San Francisco (SFO) to Charlottetown (YYG)

This cottage features a terrace, barbecue grills, and free self parking. A garden and a picnic area are also provided.

The Hotel on Pownal

Downtown Charlottetown

$1,974

per person

Jun 28 - Jul 4

found 1 day ago

Roundtrip non-stop flight included

San Francisco (SFO) 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

Downtown Charlottetown

$1,930

per person

Jun 28 - Jul 4

found 1 day ago

Roundtrip non-stop flight included

San Francisco (SFO) 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 Holman Grand Hotel

Downtown Charlottetown

$2,195

per person

Jun 28 - Jul 4

found 1 day ago

Roundtrip non-stop flight included

San Francisco (SFO) to Charlottetown (YYG)

A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and laundry facilities.

Blackbush Beach Resort

$2,048

per person

Jun 28 - Jul 4

found 1 day ago

Roundtrip non-stop flight included

San Francisco (SFO) to Charlottetown (YYG)

4 hot tubs, an outdoor pool, and a 24-hour gym are all featured at this luxury resort. Enjoy the sauna and free perks like continental breakfast and free self parking. You'll find a restaurant and a bar/lounge onsite for dining and drinks, along with a 24-hour front desk.

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

$150 nightly

$172 total

May 20 - May 21

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.

Pool

Hot Tub

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

Chrysostome PE

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Stay at this farm stay in Saint Chrysostome. Enjoy air conditioning.

Oceanfront PEI Home with Ocean Views, Wraparound Deck & Private Beach

Coleman PE

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This cottage featured laundry facilities and barbecue grills.

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

Coleman PE

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

Kitchen

Washer

Riverside Landing Cottage

Alberton PE

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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

BH Beach House

Saint Louis PE

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This vacation home features laundry facilities.

Washer

Dryer

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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

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.

Frequently asked questions

How much are vacation packages to O'Leary?

You might be pleasantly surprised — you can vacation in O'Leary for only $1,536. 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.