Pickering Vacations from $491

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Your Pickering Vacation

With plenty of highlights as well as hidden gems, this city is best explored with a Pickering vacation package. Check out hotels located in Port Union, which is great for watersports, cycling and views. If your trip to Pickering includes a little sightseeing, visit famous attractions like Rotary Park, Herongate Barn Theatre and Annandale Golf and Country Club. Expedia has what you need to escape the everyday. Tailor your vacation to Pickering to match your travel style, whatever that may be!

The Latest Pickering vacation packages

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

The Waterside Inn

3.5 out of 5
Port Credit
Price was $724, price is now $491 per person
$491
per person
Jan 14 - Jan 18
found 14 hours ago
Roundtrip flight included
New York (JFK) to Toronto (YYZ)
8.6/10 Excellent! (1,146 reviews)

1 Hotel Toronto

1 Hotel Toronto

5 out of 5
Downtown Toronto
Price was $1,685, price is now $1,067 per person
$1,067
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip flight included
Miami (MIA) to Toronto (YYZ)
9.6/10 Exceptional! (851 reviews)
.

Reviewed on Nov 3, 2026

Sandman Hotel Hamilton

Sandman Hotel Hamilton

3.5 out of 5
Lakeley
Price was $866, price is now $609 per person
$609
per person
Jan 6 - Jan 13
found 12 hours ago
Roundtrip flight included
New York (NYC) to Toronto (YYZ)
8.8/10 Excellent! (2,000 reviews)

Vittoria Hotel and Suites

Vittoria Hotel and Suites

3.5 out of 5
Clifton Hill
Price was $841, price is now $599 per person
$599
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip flight included
New York (JFK) to Toronto (YYZ)
9.2/10 Wonderful! (9,009 reviews)
Overall its nice and relaxing stay, hot tub reqlly did make it worth it.

Reviewed on Nov 5, 2026

Sterling Inn & Spa - an Ontario's Finest Inn

Sterling Inn & Spa - an Ontario's Finest Inn

4 out of 5
Clifton Hill
Price was $895, price is now $643 per person
$643
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip flight included
New York (JFK) to Toronto (YYZ)
9.6/10 Exceptional! (2,556 reviews)
Very good

Reviewed on Nov 5, 2026

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Where to stay in Pickering

Find the best Pickering areas and neighborhoods for the activities you enjoy most. Learn more about Pickering
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Lamoreaux

While Lamoreaux isn't home to many top sights, Pickering Casino Resort and Glen Cedars Golf Club are some notable places to visit nearby.

Find hotels in Lamoreaux

Stay near popular Pickering attractions

Pickering Casino Resort

9.0/10 (4 reviews)
This premier entertainment resort boasts over 2,200 slot machines and 90 table games in vibrant surroundings. Enjoy fine dining at Copperhorn Meet House or catch a show at The Arena's state-of-the-art venue.
See properties

What to do in Pickering

Treewalk Village Stouffville Treehouse Adventure for Kids

Treewalk Village Stouffville Treehouse Adventure for Kids

$8
per adult
Treewalk Village Stouffville Treehouse Adventure for Kids
Premier Sushi-Making Class in Toronto

Premier Sushi-Making Class in Toronto (Includes 5-Course Meal)

$91
per adult
Premier Sushi-Making Class in Toronto (Includes 5-Course Meal)
Small Group: Montreal and Quebec 3-Day Tour From Toronto

Small Group: Montreal and Quebec 3-Day Tour From Toronto

$766
per adult
90% of travellers recommend
Small Group: Montreal and Quebec 3-Day Tour From Toronto
See all activities in Pickering

Pickering Hotel Deals

Pickering Casino Resort Hotel

Pickering Casino Resort Hotel

4 out of 5
888 Durham Live Ave Pickering ON
9/10 Wonderful! (4,905 reviews)
"They are on strike so there is no amenities minimal staff and no food. Nothing around either and uber can5 get into the hotel to drop you off. You have to walk out to the Main Street. Not ideal."

Reviewed on Nov 3, 2026

Get rates
Pickering Casino Resort Hotel
Holiday Inn Toronto Downtown Centre by IHG

Holiday Inn Toronto Downtown Centre by IHG

3.5 out of 5
30 Carlton Street Toronto ON
Fully refundable
$140 nightly
The price is $168 total per night from Dec 6 to Dec 7
$168 total
Dec 6 - Dec 7
Total with taxes and fees
8.6/10 Excellent! (6,784 reviews)
"The staff were friendly and helpful. Breakfast was enjoyable and decent. Nice location. The room was slightly small and definitely looked like it had some natural wear and tear. One thing that I didn’t like is i got an additional charge and after looking at the invoice (which was provided after check ..."

Reviewed on Nov 5, 2026

Holiday Inn Toronto Downtown Centre by IHG
Chelsea Hotel, Toronto

Chelsea Hotel, Toronto

4 out of 5
22 Elm St Toronto ON
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $171 total per night from Dec 6 to Dec 7
$171 total
Dec 6 - Dec 7
Total with taxes and fees
8.8/10 Excellent! (2,741 reviews)
"Avoid the breakfast buffet, overpriced and lacking variety! We didn’t inquire as to price as the hostess implied that it was included after taking my room number. Since I had upgraded my room for 2 nights from a single queen to a 2 bed with balcony (an added $120+ @ night) It seemed reasonable that ..."

Reviewed on Nov 5, 2026

Chelsea Hotel, Toronto
See all 6,152 properties in Pickering
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.

Find the Best Pickering Vacation Packages

Pickering Essential Information

Language
English
Currency
Canadian dollars
Closest Airport
Billy Bishop Toronto City Airport (YTZ)
Population
87,800
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Canadian Automotive Museum, Herongate Barn Theatre and Parkwood Estate

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Frequently asked questions

Is Pickering better suited for a beach vacation or a cultural trip?
Pickering is primarily an urban destination, known for its city attractions and rich history. Its past includes thousands of years as Aboriginal territory, with archeological remains like the Draper Site, and early European encounters noted by French missionaries on Frenchman's Bay.

For cultural experiences, a Pickering vacation can include visiting the Pickering Museum Village, which features 19 heritage buildings, or exploring public art installations such as Geordie Lishman's Spirit of Pickering sculptures in Esplanade Park. The city also hosts annual events like Artfest Pickering and the Pickering Dragon Boat Festival.

Pickering offers waterfront parks like Bluffer's Park and Port Perry Waterfront, and is well-suited for urban exploration and cultural discovery.
How can I save money on a Pickering vacation package?
When you bundle, you can save up to 30%*. To save money on a Pickering package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What are the top things to do in Pickering?
A Pickering vacation offers a mix of urban attractions, natural spaces, and entertainment:

Browse and book things to do in Pickering on Expedia.
Do you need to rent a car in Pickering, or is public transport enough?
For a Pickering vacation package with flights, you have options for getting around, combining public transit with the flexibility of a car.

Durham Region Transit provides local bus services throughout the city, and the Pickering GO station offers public rail transit on an east-west axis, connecting to the downtown core. This can be convenient for exploring central areas.

However, with major highways like 401 and 407 ETR running through the area, a rental car offers more flexibility for exploring attractions further afield, such as Rouge National Urban Park or Fallsview Indoor Waterpark. Local taxis and ride-share apps are also available. Travelers arriving at Toronto Pearson International Airport (YYZ) can arrange ground transportation from there.
Can I change or cancel my Pickering vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Pickering vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Pickering vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Pickering vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Pickering?
To find last-minute vacation packages to Pickering, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Pickering vacation packages?
Free cancellation on a Pickering vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Pickering vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Pickering getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Pickering vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.