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.
Altitude Suites on Yonge
Downtown Toronto
CA $1,668
per person
Oct 18 - Oct 22
found 11 hours ago
Roundtrip flight included
Halifax (YHZ) to Toronto (YYZ)
9/10 Wonderful! (84 reviews)
Great size for our family of 5. Walk to CN Tower, Rogers Centre etc was about 30 mins, with 3 teenagers. Quiet area, very safe. The apartment was clean, and had all the facilities you would expect and the building was secure. The host was helpful, and effeicent. Overall a great experience.
Reviewed on Apr 9, 2026
Ready to book your vacation to Pickering?
Pickering Hotel Deals
Pickering Casino Resort Hotel
888 Durham Live Ave Pickering ON
CA $145
CA $182 total
Sep 8 - Sep 9
includes taxes & fees
Chelsea Hotel, Toronto
33 Gerrard St W Toronto ON
Fully refundableReserve now, pay when you stay
CA $220
CA $264 total
Sep 7 - Sep 8
includes taxes & fees
9/10 Wonderful! (1,086 reviews)
"Great experience"
Reviewed on Aug 11, 2026
Fairmont Royal York
100 Front St West Toronto ON
Fully refundableReserve now, pay when you stay
CA $297
CA $355 total
Aug 30 - Aug 31
includes taxes & fees
9/10 Wonderful! (8,544 reviews)
"The hotel itself is gorgeous. The room was a little underwhelming. Not up to date, but does the job. Very comfy overall. We did have an issue with a sewage smell coming from our washroom halfway during our stay so that was a bit inconvenient but I know it’s not on purpose"
Reviewed on Aug 11, 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.
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. Stroll along the lakeside or visit the shops in this family-friendly 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.
Millennium Square
You can find out about the history of Pickering with a stop at Millennium Square. 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 $828 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.
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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.
