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.
City Central Residences Downtown Toronto
StaysToronto
Maple Leaf Square
The Waterside Inn
Hotel Riu Plaza Toronto

Where to stay in Pickering

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

Ready to book your vacation to Pickering?

 

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Pickering Hotel Deals

Pickering Casino Resort Hotel

Pickering Casino Resort Hotel

4 out of 5
888 Durham Live Ave Pickering ON
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Nov 16 to Nov 17
CA $135
CA $170 total
Nov 16 - Nov 17
includes taxes & fees
9/10 Wonderful! (4,879 reviews)
"Arrived with international luggage. The check-in set up is inconvenient for parking and transporting luggage to your room. There was a lovely girl who helped me get my bags to my room. The reception staff have a lot to learn from her. She was so welcoming and lovely. The reception staff were not ..."

Reviewed on Nov 15, 2026

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
The price is CA $184 per night from Dec 14 to Dec 15
CA $184
CA $220 total
Dec 14 - Dec 15
includes taxes & fees
8.6/10 Excellent! (6,842 reviews)
"Beds are very uncomfortable and very noisy at night. Staff were not so helpful ."

Reviewed on Nov 15, 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
The price is CA $183 per night from Dec 16 to Dec 17
CA $183
CA $219 total
Dec 16 - Dec 17
includes taxes & fees
Chelsea Hotel, Toronto
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

What to do in Pickering

Frequently asked questions

How much does a Pickering vacation package cost?
Offering excellent value package deals from CA $721 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.