Pickering Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Eric & Kristy's Adventures

  • Plan, book, travel with confidence

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    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Pickering Vacation Packages

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 ₩126,919 per night from Sep 1 to Sep 2
₩126,919
₩160,559 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (3,096 reviews)
"A lot of food option within the hotel, clean room and staff very friendly and helpful."

Reviewed on Aug 11, 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 ₩205,187 per night from Sep 1 to Sep 2
₩205,187
₩251,570 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (11,987 reviews)
New self check-in
"The stay was great as always, location central to restaurants and tourist attractions, super close to Little Canada which we spent hours in. The best update at the hotel was the self check in and out kiosks which even program and spit out your keys. No more lines!"

Reviewed on Aug 11, 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
The price is ₩205,036 per night from Sep 1 to Sep 2
₩205,036
₩251,386 total
Sep 1 - Sep 2
includes taxes & fees
8.4/10 Very Good! (4,432 reviews)
"The hotel was very nice and clean. The staff was very nice also. It was in a area that was walkable to shopping and dining. Also, the dining choices was excellent. The only thing I didn't like about the hotel was the cost for the breakfast."

Reviewed on Aug 11, 2025

Holiday Inn Toronto Downtown Centre by IHG
See all 4,168 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.

Frequently asked questions

How much does a Pickering vacation package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a vacation to Pickering costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Pickering?
You can typically find lower rates and greater availability in January, February and March. Check out our cheap Pickering vacation packages and you could score some excellent off-season deals.
How many days is enough for Pickering?
The ideal duration of your Pickering vacation depends on what you'd like to do. Usually, a few days to a week will give you time to visit all the leading sights and explore some hidden treasures along the way.
How to find the best Pickering package deals?
Finding a cheap Pickering package deal is a breeze with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget, add a couple of filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to view the most affordable Pickering package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Pickering vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll generally get a better deal than booking each component individually. And you'll still have the flexibility to create a tailored Pickering vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Pickering?
If you've got your Pickering travel dates finalized, book as soon as you can to snap up some fantastic deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are ideal for traveling on a whim.
How to plan a trip to Pickering?

  1. Pick your dates: What you want to do in Pickering and your favorite season will help you decide when to go.
  2. Calculate your budget: Make sure you have enough money to pay for everything from food and transportation to experiences and flights. Your accommodations will probably be the biggest expense during your trip to Pickering.
  3. Determine how many days away: Start by listing all the activities and sights you'd like to experience in Pickering. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to find 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.