Pickering Vacations from $765

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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.
BightStays

BightStays

3.5 out of 5
Downtown Toronto
Save 100% on your flight
Price was $1,106, price is now $765 per person
$765
per person
Mar 18 - Mar 22
found 1 day ago
Roundtrip flight included
New York (NYC) to Toronto (YYZ)
7.2/10 Good! (54 reviews)
The room was clean and comfortable.

Reviewed on Nov 9, 2025

151 Dan Leckie Way

151 Dan Leckie Way

2.5 out of 5
Downtown Toronto
Save 100% on your flight
Price was $1,439, price is now $898 per person
$898
per person
Mar 18 - Mar 22
found 1 day ago
Roundtrip flight included
New York (NYC) to Toronto (YYZ)
9.2/10 Wonderful! (278 reviews)
The place was very clean and beautiful decorated. The laundry machine was a life saver, and Sam was always available to answer questions and help. We enjoyed this place!!!

Reviewed on Dec 22, 2025

1 Hotel Toronto

1 Hotel Toronto

5 out of 5
Downtown Toronto
Save 100% on your flight
Price was $2,840, price is now $1,881 per person
$1,881
per person
Feb 8 - Feb 15
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
9.4/10 Exceptional! (632 reviews)
I forgot something in the room and the staff had it saved for me and returned it only if I had my ID. Terrific service I’ve been to places where they would’ve said it’s gone you forgot it but 1 Hotel Toronto cares about their clientele

Reviewed on Jan 2, 2026

Hotel Riu Plaza Toronto

Hotel Riu Plaza Toronto

4 out of 5
Downtown Toronto
Price was $2,081, price is now $1,429 per person
$1,429
per person
Mar 25 - Mar 31
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Toronto (YYZ)
9.2/10 Wonderful! (451 reviews)
The breakfast was the best breakfast I have ever had at a hotel and the location is perfect for seeing a show at the Princess of Wales Theatre.

Reviewed on Jan 3, 2026

HostlyStays Luxury Suites

HostlyStays Luxury Suites

2 out of 5
Downtown Toronto
Save 100% on your flight
Price was $2,643, price is now $1,841 per person
$1,841
per person
Mar 18 - Mar 22
found 1 day ago
Roundtrip flight included
New York (NYC) to Toronto (YYZ)
10/10 Exceptional! (1 review)
Wasn't aware that this was for a single bedroom in a shared condo space with other guests occupying the other bedrooms, from the information given in the listing. Regardless, had an excellent stay and the price was unbeatable, once again hostlystays is above and beyond in value for money and guest relations are always A+++ will always reccommend staying here

Reviewed on Dec 15, 2025

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Discover the most popular places to visit in Pickering

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

Luke Andrews Wood Sculptures

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.

Luke Andrews Wood Sculptures

What to do in Pickering

Premier Sushi-Making Class in Toronto

Premier Sushi-Making Class in Toronto (Includes 5-Course Meal)

$94
per adult
Premier Sushi-Making Class in Toronto (Includes 5-Course Meal)
See all activities in Pickering

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
$83 nightly
The price is $98 total per night from Jan 5 to Jan 6
$98 total
Jan 5 - Jan 6
Total with taxes and fees
9/10 Wonderful! (3,968 reviews)
Clean

Reviewed on Jan 3, 2026

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
$117 nightly
The price is $143 total per night from Jan 7 to Jan 8
$143 total
Jan 7 - Jan 8
Total with taxes and fees
8.4/10 Very Good! (13,717 reviews)
Good location and safe place. Room is well managed and cleaned. Very good service and well communication. Strongly suggest to stay.

Reviewed on Jan 4, 2026

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
$87 nightly
The price is $106 total per night from Jan 7 to Jan 8
$106 total
Jan 7 - Jan 8
Total with taxes and fees
8.4/10 Very Good! (5,126 reviews)
What an incredible stay . Close to everything. Thanks

Reviewed on Jan 2, 2026

Holiday Inn Toronto Downtown Centre by IHG
See all 4,521 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.

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 $765 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?

  1. Pick your dates: What you'd like to do in Pickering and your favorite season can help you decide when to travel.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.