Pickering Vacations from $371
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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!
The Latest Pickering vacation packages
Price found within the past 48 hours. Click for updated prices.
Cabbagetown Inn
Downtown Toronto
$632
per person
Dec 9 - Dec 14
found 22 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Toronto (YYZ)
8.6/10 Excellent! (101 reviews)
We had a great stay here, the location is convenient to everywhere, all within half hour walk basically. And it has shoppers, Dollarama, grocery stores across the street, so many restaurants choices on the street as well
Reviewed on Sep 27, 2026
Where to stay in Pickering
Find the best Pickering areas and neighborhoods for the activities you enjoy most. Learn more about Pickering
Lamoreaux
While Lamoreaux isn't home to many top sights, Pickering Casino Resort and Glen Cedars Golf Club are some notable places to visit nearby.
West Shore
If you're spending some time in West Shore, Lake Ontario and Petticoat Creek Conservation Area are top sights worth seeing.
Bay Ridges
2 out of top 10 points of interest in this area
While visiting Bay Ridges, you might make a stop by sights like Lake Ontario and Beachfront Park.
City Centre
2 out of top 10 points of interest in this area
While you're in City Centre, take in top sights like Pickering Town Centre and jump on the metro at Pickering Station to see more of the city.
Liverpool
Though Liverpool might not have many top sights, you can venture to the surrounding area to see attractions like Toronto Zoo and Pickering Casino Resort.
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.
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.
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.
Pickering Town Centre
You can do some window-shopping at Pickering Town Centre during your visit to Pickering.
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.
Claremont Nature Centre
You can take time to visit Claremont Nature Centre during your travels to Pickering. Stroll along the lakeside or visit the shops in this family-friendly area.
What to do in Pickering
Treewalk Village Stouffville Treehouse Adventure for Kids
$8
per adult
Premier Sushi-Making Class in Toronto (Includes 5-Course Meal)
$92
per adult
Small Group: Montreal and Quebec 3-Day Tour From Toronto
$766
per adult
90% of travellers recommend
Pickering Hotel Deals
Pickering Casino Resort Hotel
888 Durham Live Ave Pickering ON
$80 nightly
$94 total
Nov 2 - Nov 3
Total with taxes and fees
Toronto Don Valley Hotel and Suites
175 Wynford Drive Toronto ON
$107 nightly
$128 total
Nov 1 - Nov 2
Total with taxes and fees
7.8/10 Good! (7,141 reviews)
"Awesome stay."
Reviewed on Oct 2, 2026
Chelsea Hotel, Toronto
22 Elm St Toronto ON
Fully refundableReserve now, pay when you stay
$143 nightly
$171 total
Oct 11 - Oct 12
Total with taxes and 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.
Find the Best Pickering Vacation Packages
Pickering Essential Information
Language | English |
|---|---|
Currency | Canadian dollars |
Closest Airport | Billy Bishop Toronto City Airport (YTZ) |
Population | 87,800 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | Canadian Automotive Museum, Herongate Barn Theatre and Parkwood Estate |
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Frequently asked questions
How much does a Pickering vacation package cost?
Offering great value package deals from $371 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 generally find lower rates and better availability in January, February and October. Explore our cheap Pickering vacation packages and you could score some great off-season discounts.
How many days is enough for Pickering?
The ideal duration of your Pickering vacation depends on what you'd like to see. Generally, a few days to a week will give you plenty of time to visit all the top sights and discover 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'd like to do in Pickering and your favorite season can help you decide when to travel.
- Plan your budget wisely: In addition to the price of your accommodations, you'll need to consider other expenses too. These include transportation, food and flights. Also, put aside a little extra for unexpected costs that may crop up during your trip to Pickering.
- Explore Pickering with Expedia's trip planning tool: Gain insights into the top attractions and best hotels for your trip to Pickering. You can also save your favorite locations, collaborate with friends and family and organize your plans in one place.
- Decide your trip length: Think about how much time you'd like to spend discovering Pickering. Plan your itinerary so you can get to all the attractions and activities you're interested in at a comfortable pace.
- Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to choose a Pickering vacation package that brings all your bookings together.
- Book any activities or excursions: Here's the fun part — locking in everything you want to see and do. Browse some of the incredible things to do in Pickering and book your tickets in advance to save time (and maybe some money too!).
Does Expedia offer Book Now, Pay Later Pickering vacation packages?
Secure your perfect trip to Pickering with help from Expedia's Book Now, Pay Later vacations. No need to save like crazy or wait for your next payday — we've joined forces with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans mean you can spread the total cost across 3, 6 or 12 months. With no late payment fees or hidden charges, it's easy to stay on budget and snag great deals before they disappear.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
