Pickering Vacations from $946
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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.
Where to stay in Pickering
Find the best Pickering areas and neighborhoods for the activities you enjoy most. Learn more about Pickering
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.
West Shore
If you're spending some time in West Shore, Lake Ontario and Petticoat Creek Conservation Area are top sights worth seeing.
Bay Ridges
1 out of top 10 points of interest in this area
While visiting Bay Ridges, you might make a stop by sights like Lake Ontario and Beachfront Park.
City Centre
3 out of top 10 points of interest in this area
While you're in City Centre, take in top sights like Pickering Town Centre and jump on the metro at Pickering Station to see more of the city.
Liverpool
Though Liverpool might not have many top sights, you can venture to the surrounding area to see attractions like Toronto Zoo and Pickering Casino Resort.
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.
Deer Creek North Golf Course
8.6/10 (7 reviews)
This championship golf course features three distinct nine-hole layouts with strategic challenges and undulating greens. Enjoy a round on meticulously maintained fairways before relaxing at Jerry's Taphouse afterward.
Glen Cedars Golf Club
7.4/10 (6 reviews)
This parkland-style course offers strategic play through mature tree-lined fairways and rolling terrain. Book a morning tee time for the best experience on this challenging yet scenic 18-hole layout.
Beachfront Park
Why not spend a lazy afternoon at Beachfront Park during your trip to Pickering? Stroll along the lakeside or visit the shops in this family-friendly area.
Millennium Square
Millennium Square provides stunning Lake Ontario views and serves as a community gathering spot. Enjoy Thursday Night Summer Concerts or monthly public star parties for a magical lakeside experience.
Pickering Town Centre
You can do some window-shopping at Pickering Town Centre during your visit to Pickering.
Cineplex Cinemas Pickering
This upscale cinema offers premium movie experiences with VIP auditoriums featuring reclining seats and in-seat dining. Enjoy the adults-only lounge with craft cocktails before watching the latest blockbusters.
Claremont Nature Centre
You can take time to visit Claremont Nature Centre during your travels to Pickering. Stroll along the lakeside or visit the shops in this family-friendly area.
What to do in Pickering
Treewalk Village Stouffville Treehouse Adventure for Kids
$8
per adult
Premier Sushi-Making Class in Toronto (Includes 5-Course Meal)
$92
per adult
Small Group: Montreal and Quebec 3-Day Tour From Toronto
$766
per adult
90% of travellers recommend
Pickering Hotel Deals
Pickering Casino Resort Hotel
888 Durham Live Ave Pickering ON
$93 nightly
$109 total
Nov 1 - Nov 2
Total with taxes and fees
9/10 Wonderful! (4,980 reviews)
"Hotel location, service and amenities deplorable. There is no microwave in the hotel room and when asked about it, the hotel desk employee was very rude and said there was an additional charge if we wanted one. There was an employee strike that made access to and from the hotel horrible, the employees ..."
Reviewed on Oct 6, 2026
Chelsea Hotel, Toronto
22 Elm St Toronto ON
Fully refundableReserve now, pay when you stay
$143 nightly
$171 total
Oct 11 - Oct 12
Total with taxes and fees
Holiday Inn Toronto Downtown Centre by IHG
30 Carlton Street Toronto ON
Fully refundable
$123 nightly
$148 total
Nov 1 - Nov 2
Total with taxes and fees
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
