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.
The Waterside Inn
Port Credit
CA $695
per person
Nov 14 - Nov 18
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Toronto (YYZ)
8.6/10 Excellent! (1,040 reviews)
Room was nice and the view was great, could see the CN tower and Lake Ontario. Was much cheaper due to balcony construction but didn’t really bother us.
Reviewed on Aug 21, 2026
Union Hotel
Downtown Toronto
CA $1,029
per person
Oct 26 - Oct 31
found 21 hours ago
Roundtrip flight included
Edmonton (YEG) to Toronto (YYZ)
9.2/10 Wonderful! (2,404 reviews)
Excellent staff, hospitality and great rooms & pillows. Will definitely stay here again and recommend to friends and family
Reviewed on Aug 21, 2026
Finlay House Bed and Breakfast Niagara - on - the - Lake
Old Town Historic District
CA $979
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Toronto (YYZ)
9.4/10 Exceptional! (246 reviews)
Our stay was wonderful! The room was lovely and extremely comfortable. Yvonne was a perfect hostess, very friendly and welcoming. She answered all our questions and gave us great information on what to see and do. The breakfasts were delicious too, served promptly, and with great attention to detail. Overall, we couldn’t be more pleased with our stay and look forward to visiting again in the future!
Reviewed on Aug 1, 2026
Where to stay in Pickering
Find the best Pickering areas and neighborhoods for the activities you enjoy most. Learn more about Pickering
West Shore
If you're spending some time in West Shore, Lake Ontario and Petticoat Creek Conservation Area are top sights worth seeing.
Amberlea
While there might not be top attractions in Amberlea, you can explore the larger area and discover places like Toronto Zoo and Rouge National Urban Park.
Brock Ridge
If you're looking for some top things to see and do in Brock Ridge and surrounding area, you can visit Pickering Casino Resort and Rouge National Urban Park.
Duffin Heights
While Duffin Heights isn't home to many top sights, Pickering Casino Resort and Herongate Barn Theatre are some notable places to visit nearby.
Highbush
While Highbush might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Rouge National Urban Park and Toronto Zoo.
Ready to book your vacation to Pickering?
Pickering Hotel Deals
Pickering Casino Resort Hotel
888 Durham Live Ave Pickering ON
CA $139
CA $174 total
Sep 21 - Sep 22
includes taxes & fees
9/10 Wonderful! (5,090 reviews)
"Arrived to picketers at the main road in , had to wait for 5 minutes before they let us in. Arrived at the front desk a realized we should have not stayed there. We were on the highway for 11 hours without eating and all that was open at 9 pm was an oriental take out with virtually no food left. ..."
Reviewed on Aug 21, 2026
Chelsea Hotel, Toronto
33 Gerrard St W Toronto ON
Fully refundableReserve now, pay when you stay
CA $229
CA $274 total
Sep 7 - Sep 8
includes taxes & fees
9/10 Wonderful! (1,319 reviews)
"Staff was very helpful especially housekeeping"
Reviewed on Aug 21, 2026
Fairmont Royal York
100 Front St West Toronto ON
Fully refundableReserve now, pay when you stay
CA $322
CA $386 total
Sep 7 - Sep 8
includes taxes & 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.
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.
Herongate Barn Theatre
8.4/10 (6 reviews)
You can get tickets for a performance at Herongate Barn Theatre on your trip to Pickering. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
Cineplex Cinemas Pickering
You can take time to visit Cineplex Cinemas Pickering during your travels to Pickering.
Millennium Square
Learn about the local history of Pickering with a stop at Millennium Square.
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.
Luke Andrews Wood Sculptures
7.0/10 (2 reviews)
You can spend time browsing the exhibits at Luke Andrews Wood Sculptures during your travels in Pickering. You can attend a sporting event while in the area.
What to do in Pickering
3 Day Eastern Canada Tour Toronto Montreal Quebec and Ottawa
CA $802
per adult
From Toronto: Small Group 4-Day Eastern Canada Tour
CA $1,561
per adult
Frequently asked questions
How much does a Pickering vacation package cost?
Offering excellent value package deals from CA $695 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.
