Pickering Vacations
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Find the Best Pickering Vacation Packages
Pickering Hotel Deals
Pickering Casino Resort Hotel
888 Durham Live Ave Pickering ON
₩127,594
₩161,424 total
Sep 13 - Sep 14
includes taxes & fees
Chelsea Hotel, Toronto
33 Gerrard St W Toronto ON
Fully refundableReserve now, pay when you stay
₩232,409
₩278,379 total
Sep 7 - Sep 8
includes taxes & fees
9/10 Wonderful! (1,282 reviews)
"Very clean and professional. Would book that hotel again"
Reviewed on Aug 19, 2026
Fairmont Royal York
100 Front St West Toronto ON
Fully refundableReserve now, pay when you stay
₩344,726
₩412,913 total
Sep 7 - Sep 8
includes taxes & fees
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
Pickering Casino Resort
9.0/10 (4 reviews)
This premier entertainment resort boasts over 2,200 slot machines and 90 table games in vibrant surroundings. Enjoy fine dining at Copperhorn Meet House or catch a show at The Arena's state-of-the-art venue.
Deer Creek North Golf Course
8.6/10 (7 reviews)
This championship golf course features three distinct nine-hole layouts with strategic challenges and undulating greens. Enjoy a round on meticulously maintained fairways before relaxing at Jerry's Taphouse afterward.
Herongate Barn Theatre
8.4/10 (6 reviews)
This century-old dairy barn transforms into a stage for comedy and mystery while you dine. Savor comfort food in the original bull pen before ascending to the Hayloft Theatre for an evening of rustic charm.
Cineplex Cinemas Pickering
This upscale cinema offers premium movie experiences with VIP auditoriums featuring reclining seats and in-seat dining. Enjoy the adults-only lounge with craft cocktails before watching the latest blockbusters.
Millennium Square
Millennium Square provides stunning Lake Ontario views and serves as a community gathering spot. Enjoy Thursday Night Summer Concerts or monthly public star parties for a magical lakeside experience.
Glen Cedars Golf Club
7.4/10 (6 reviews)
This parkland-style course offers strategic play through mature tree-lined fairways and rolling terrain. Book a morning tee time for the best experience on this challenging yet scenic 18-hole layout.
Beachfront Park
Why not spend a lazy afternoon at Beachfront Park during your trip to Pickering? Stroll along the lakeside or visit the shops in this family-friendly area.
Luke Andrews Wood Sculptures
7.0/10 (2 reviews)
You can spend time browsing the exhibits at Luke Andrews Wood Sculptures during your travels in Pickering. You can attend a sporting event while in the area.
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?
- Pick your dates: What you want to do in Pickering and your favorite season will help you decide when to go.
- 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.
- 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.
- 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.
