Pickering Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Eric & Kristy's Adventures

Top hotels in Pickering

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 2.665.796 ₫ per night from 1 Sept to 2 Sept
2.665.796 ₫
3.348.407 ₫ total
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (3,048 reviews)
"A little pricy still"

Reviewed on 4 Aug 2025

Pickering Casino Resort Hotel
Chelsea Hotel, Toronto

Chelsea Hotel, Toronto

4 out of 5
33 Gerrard St W, Toronto, ON
The price is 4.041.081 ₫ per night from 1 Sept to 2 Sept
4.041.081 ₫
4.954.567 ₫ total
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (11,877 reviews)
"Family friendly! The family pool area offers a lot! There's a teens lounge that includes a billiards table and arcade. An activity center for the littles with tons of games and even some furry animal friends. The pool has a corkscrew slide which will make even the adults smile. The adult pool and ..."

Reviewed on 7 Aug 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 3.875.925 ₫ per night from 1 Sept to 2 Sept
3.875.925 ₫
4.752.113 ₫ total
1 Sept - 2 Sept
includes taxes & fees
8.4/10 Very Good! (4,385 reviews)
"I nice hotel in a nice location and a good price"

Reviewed on 4 Aug 2025

Holiday Inn Toronto Downtown Centre by IHG
See all 4,161 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.

Popular places to visit

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 during your stay in 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

Frequently asked questions

How much does a Pickering holiday package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a holiday 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 holiday packages and you could score some excellent off-season deals.
How many days is enough for Pickering?
The ideal duration of your Pickering holiday 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 travelling on a weekday, when prices are often lower.
Is it cheaper to book a Pickering holiday as a package?
Expedia holiday 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 holiday by choosing your preferred type of stay, airline and car class.
When to book a holiday 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 travelling on a whim.
How to plan a trip to Pickering?

  1. Pick your dates: What you want to do in Pickering and your favourite 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 accommodation 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 holiday package that brings all your bookings together.