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 Marriott City Centre Hotel

Toronto Marriott City Centre Hotel

4 out of 5
Downtown Toronto
per person
Sep 22 - Sep 25
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Toronto (YYZ)
9.2/10 Wonderful! (1,395 reviews)
Very nice staff, great room!!

Reviewed on Aug. 9, 2025

151 Dan Leckie Way

151 Dan Leckie Way

2.5 out of 5
Downtown Toronto
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Toronto (YYZ)
9.2/10 Wonderful! (241 reviews)
I can’t rate this property as we did not stay there. They switched us property because of plumbing issues. For the property that we did stay at, the futon couch was broken and all bended. We put the mattress on the floor so we could use it as a bed. One of the bedrooms was way to tall for a rental property. There was 2 boxsprings and a mattress. The only seating there was, were barstools and bar height flimsy chairs. We had to be in all different rooms when we were at the Condo. The location was good.

Reviewed on Jul. 31, 2025

Woodbourne Inn

Woodbourne Inn

4 out of 5
St. Davids
per person
Sep 18 - Sep 23
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Toronto (YYZ)
9.8/10 Exceptional! (490 reviews)
We had a wonderful stay! Yvonne and the entire staff was incredibly responsive and friendly, the room was clean and spacious, and the outdoor seating area was lovely. We also enjoyed the indoor game room too, such a nice touch!

Reviewed on Aug. 4, 2025

1 Hotel Toronto

1 Hotel Toronto

5 out of 5
Downtown Toronto
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Toronto (YYZ)
9.4/10 Exceptional! (569 reviews)
Excellent experience staying at 1 hotel. Very clean hotel and very attentive staff with easy communication via text. Loud neighbours partying in middle of night next door keeping us up but as soon as we notified the hotel staff they ensured the problem was resolved quickly.

Reviewed on Aug. 6, 2025

Mount Alverno Luxury Resorts

Mount Alverno Luxury Resorts

2.5 out of 5
per person
Sep 22 - Sep 26
found 15 hours ago
Roundtrip flight included
Edmonton (YEG) to Toronto (YYZ)
9/10 Wonderful! (299 reviews)
Lovely peaceful stay, close to Orangeville. Nice brewery across the street. Nice experience and got a good deal.

Reviewed on Aug. 9, 2025

Ready to book your vacation to Pickering?

 

Choose your dates

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 $143 per night from Sep 1 to Sep 2
CA $143
CA $180 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (3,068 reviews)
In town for a funeral-stress free stay
"Wonderful hotel. Staff friendly and helpful. Room was clean and beautiful. Beds were very comfortable. Plenty of food options even late at night."

Reviewed on Aug. 7, 2025

Pickering Casino Resort Hotel
Chelsea Hotel, Toronto

Chelsea Hotel, Toronto

4 out of 5
33 Gerrard St W, Toronto, ON
Fully refundableReserve now, pay when you stay
The price is CA $203 per night from Sep 1 to Sep 2
CA $203
CA $249 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (11,907 reviews)
"It was comfortable and quiet, we had what needed in the room and the check-in was easy and not confusing at all."

Reviewed on Aug. 9, 2025

Chelsea Hotel, Toronto
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 $203 per night from Sep 1 to Sep 2
CA $203
CA $249 total
Sep 1 - Sep 2
includes taxes & fees
8.4/10 Very Good! (4,405 reviews)
Great location
"First of all, Paulette in housekeeping gets 10/10. She was very friendly and pleasant. The hotel location is walking distance from a variety of restaurants and entertainment. I booked a suite for my son and I. The space was perfect size for 2 . He even had a half bathroom. There are some minor renovations ..."

Reviewed on Aug. 8, 2025

Holiday Inn Toronto Downtown Centre by IHG
See all 4,186 properties in Pickering
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.
All Inclusive Vacations
All Inclusive Vacations
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Discover the most popular places to visit in Pickering

Deer Creek North Golf Course

Enjoy a round of golf in Pickering at Deer Creek North Golf Course. You can attend a sporting event while in the area.

Deer Creek North Golf Course

Herongate Barn Theatre

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.

Herongate Barn Theatre

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.

Millennium Square

What to do in Pickering

Small Group: Niagara Falls Full-Day Tour from Toronto

Small Group: Niagara Falls Full-Day Tour from Toronto

CA $89
per adult
100% of travellers recommend
Small Group: Niagara Falls Full-Day Tour from Toronto
Beach day Sandbanks Provincial Park

Beach day Sandbanks Provincial Park

CA $127
per adult
Beach day Sandbanks Provincial Park
See all activities in Pickering

Frequently asked questions

How much does a Pickering vacation package cost?
Offering excellent value package deals from CA $875 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.