Pickering Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Eric & Kristy's Adventures
    deals illustration
    Better together
    Save up to CA $1,096 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    Rest easy
    Plan, book, and manage your trip all in one place

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.
Comfort Inn Pickering

Comfort Inn Pickering

2.5 out of 5
per person
Aug 12 - Aug 15
found 5 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Toronto (YYZ)
7.4/10 Good! (1,000 reviews)
It is old and it smells.

Reviewed on Jun. 26, 2025

Canada Suites on Bay

Canada Suites on Bay

4 out of 5
Downtown Toronto
Save 100% on your flight
per person
Sep 4 - Sep 11
found 14 hours ago
Roundtrip flight included
Edmonton (YEG) to Toronto (YYZ)
8.6/10 Excellent! (301 reviews)
Was a very nice room and easy to come and go. However the fire alarm got pulled at 3am on my second last night there and not because of a fire. I then couldn't go back to bed and was super tired for my meetings the next day.

Reviewed on Jun. 9, 2025

The Waterside Inn

The Waterside Inn

3.5 out of 5
Port Credit
Save 100% on your flight
per person
Sep 8 - Sep 13
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Toronto (YYZ)
8.2/10 Very Good! (1,011 reviews)
Very clean and quiet stay at this hotel. It was a great location for our visit. We appreciated the easy parking too.

Reviewed on Jul. 1, 2025

Best Western Plus Cairn Croft Hotel

Best Western Plus Cairn Croft Hotel

3 out of 5
Lundy's Lane
Save 100% on your flight
per person
Sep 9 - Sep 16
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Toronto (YYZ)
8.8/10 Excellent! (1,012 reviews)
The hotel was nice and clean. I wasn’t a fan of paying for onsite parking, maybe it’s a thing in Niagara at all hotels. Be prepared to be up at 8am if your room is in the atrium as it gets noisy. Rooms were very clean and the bed was comfortable. I’d stay here again.

Reviewed on Jul. 5, 2025

1 Hotel Toronto

1 Hotel Toronto

5 out of 5
Downtown Toronto
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Winnipeg (YWG) to Toronto (YYZ)
9.4/10 Exceptional! (526 reviews)
had a very pleasant stay. Staff was great!

Reviewed on Jul. 4, 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 $135 per night from Jul 6 to Jul 7
CA $135
CA $170 total
Jul 6 - Jul 7
includes taxes & fees
8.8/10 Excellent! (2,836 reviews)
"."

Reviewed on Jul. 3, 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 Jul 13 to Jul 14
CA $203
CA $249 total
Jul 13 - Jul 14
includes taxes & fees
8.2/10 Very Good! (11,517 reviews)
"Perfect location close to everything . If there was english breakfast tea in the room would be great 😊"

Reviewed on Jul. 5, 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 $237 per night from Jul 13 to Jul 14
CA $237
CA $291 total
Jul 13 - Jul 14
includes taxes & fees
8.4/10 Very Good! (4,233 reviews)
"I like how close this hotel is to the subway, eaton center, and many stores and restaurants. Very small room, but to be expected for its location. The hallways and lobby were super hot and not conditioned, so we had fo blast our room's AC which worked well and kept us cool in the hot weather. Could ..."

Reviewed on Jul. 5, 2025

Holiday Inn Toronto Downtown Centre by IHG
See all 4,130 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

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

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

Annandale Golf and Country Club

Enjoy a round of golf in Pickering at Annandale Golf and Country Club. While you're here, you can savor the charming coffeehouses.

Annandale Golf and Country Club

What to do in Pickering

Exhiliirate your senses

Exhilarating 120km Aerial Tour of Toronto with iflyTOTO

CA $125
per adult
Exhilarating 120km Aerial Tour of Toronto with iflyTOTO
Pamper yourself

Toronto Aerial Tour with Niagara Winery Tasting Tour with iflyTOTO

CA $310
per adult
Toronto Aerial Tour with Niagara Winery Tasting Tour with iflyTOTO
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 $548 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.