Pickering Vacation Packages
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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!
Top Pickering Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Toronto Inn York
Downtown Toronto
CA $654
per person
Nov 21 - Nov 25
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Toronto (YYZ)
8.2/10 Very good! (10 reviews)
Firstly, we had to pick up the key from a different place from the actual unit, which is so inconvenient when you are carrying luggage with you. Then we had problems finding the unit. The property is advertised as Toronto Inn York so we put this name in Google maps and we cannot find the place. We called and they said follow the address in the instructions. But it doesn’t say West or East. So we walked up and down with our luggage trying to find the place. They should specify in the instructions NOT to put Toronto inn York in Google maps. The check-in process definitely needs improvement. No complaints on the unit; location is good, and the unit is clean, spacious and has a great view of the city.
Reviewed on Sep 24, 2026
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
2 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
2 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.
Ready to book your vacation to Pickering?
Pickering Hotel Deals
Toronto Don Valley Hotel and Suites
175 Wynford Drive Toronto ON
CA $152
CA $182 total
Oct 26 - Oct 27
includes taxes & fees
7.8/10 Good! (7,055 reviews)
"Great staff"
Reviewed on Sep 25, 2026
Chelsea Hotel, Toronto
33 Gerrard St W Toronto ON
Fully refundableReserve now, pay when you stay
CA $209
CA $250 total
Sep 27 - Sep 28
includes taxes & fees
8.8/10 Excellent! (2,083 reviews)
"Couldn't make and they refused even a partial refund. Never again."
Reviewed on Sep 25, 2026
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 Pickering attractions
Pickering Casino Resort
9.0/10 (4 reviews)
Why not roll the dice with a visit to Pickering Casino Resort during your time in Pickering? Stroll along the lakeside or visit the shops in this family-friendly area.
Deer Creek North Golf Course
8.6/10 (7 reviews)
Enjoy a round of golf in Pickering at Deer Creek North Golf Course. You can attend a sporting event while in the area.
Glen Cedars Golf Club
7.4/10 (6 reviews)
Enjoy a round of golf in Pickering at Glen Cedars Golf Club. Attend a sporting event while in this family-friendly area or simply enjoy the top-notch restaurants.
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
Learn about the local history of Pickering with a stop at Millennium Square.
Cineplex Cinemas Pickering
You can take time to visit Cineplex Cinemas Pickering during your travels to Pickering.
What to do in Pickering
Discovery Kids Courses Treetop Trekking Stouffville
CA $31
per child
Premier Sushi-Making Class in Toronto (Includes 5-Course Meal)
CA $129
per adult
3-Day Canada Capitals Express: Montreal, Quebec, Ottawa
CA $835
per adult
Frequently asked questions
How much does a Pickering vacation package cost?
Offering excellent value package deals from CA $636 on Expedia, you'll be surprised at how little a vacation to Pickering costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Pickering?
January, February and March are the best times to look for cheap Pickering vacation packages. Opting to travel in quieter periods means you can typically find lower prices on flights and hotels.
How many days is enough for Pickering?
With a well-organized travel plan, you can easily tick off the top Pickering sights in a handful of days. But if you'd like to venture off the beaten track or take day trips, consider booking your Pickering vacation for longer.
How to find the best Pickering package deals?
Finding a cheap Pickering package deal is easy with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most wallet-friendly Pickering package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Pickering vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging stays and flights individually. Better still, you can personalize your Pickering trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
How to plan a trip to Pickering?
- Choose when to go: Check your calendar and get your bags packed. Your favourite season and the activities on offer will also help you decide when to vacation in Pickering.
- Budget wisely: Besides the cost of your hotel, you should consider other expenses too. These include transportation, food and flights. Also, put aside some extra funds for unexpected costs that may crop up during your trip to Pickering.
- Decide how long to go for: Now that you're up to speed on Pickering, you can figure out the right length of your break. Put together a rough plan and allocate enough time to get through everything on your must-do list.
- Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to choose a Pickering vacation package that brings all your bookings together.
Explore a world of travel with Expedia
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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.
