Pickering Vacations from $1,277

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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.
GLOBALSTAY. Burano Condos in Downtown Toronto

GLOBALSTAY. Burano Condos in Downtown Toronto

3 out of 5
Downtown Toronto
Save 100% on your flight
Price was $2,029, price is now $1,277 per person
$1,277
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
6.8/10 (93 reviews)
Property is located in an excellent neighborhood in a nice building. Unfortunately, the unit was cheaply furnished with an old mattress that is broken. There were some random shampoo, conditioner, toothpaste underneath the sink. The cabinet was quit dirty as well.

Reviewed on Sep 22, 2025

1 Hotel Toronto

1 Hotel Toronto

5 out of 5
Downtown Toronto
Save 100% on your flight
Price was $2,453, price is now $1,448 per person
$1,448
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
9.4/10 Exceptional! (595 reviews)
Bed, pillows, linens were excellent. Ne8eds more washroom hooks for towels and clothing.

Reviewed on Oct 4, 2025

GLOBALSTAY Modern Lillian St Apartments

GLOBALSTAY Modern Lillian St Apartments

4.5 out of 5
Old Toronto
Save 100% on your flight
Price was $2,196, price is now $1,366 per person
$1,366
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
7.2/10 Good! (117 reviews)
Absolutely amazing property, very well furnished and equipped with everything you need. They took care even of the forgotten toothbrush and paste for you - the cupboards were stuffed with everything you need for a great enjoyable stay! Grocery store with delicious ready to eat hot meals righ around the corner, close to subway, landmarks, restaurants, parks, pedestrian areas. We would come back again!

Reviewed on Oct 5, 2025

GLOBALSTAY. Modern North York Condos

GLOBALSTAY. Modern North York Condos

4 out of 5
North York
Save 100% on your flight
Price was $2,158, price is now $1,348 per person
$1,348
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
6.8/10 (151 reviews)
It is a good place to stay and family friendly.

Reviewed on Sep 17, 2025

Canada Suites on Bay

Canada Suites on Bay

4 out of 5
Downtown Toronto
Save 100% on your flight
Price was $2,347, price is now $1,470 per person
$1,470
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
8.6/10 Excellent! (304 reviews)
Was a very nice room and easy to come and go. However the fire alarm got pulled at 3am on my second last night there and not because of a fire. I then couldn't go back to bed and was super tired for my meetings the next day.

Reviewed on Jun 9, 2025

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Discover the most popular places to visit in Pickering

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

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

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
$87 nightly
The price is $102 total per night from Oct 13 to Oct 14
$102 total
Oct 13 - Oct 14
Total with taxes and fees
8.8/10 Excellent! (3,437 reviews)
"Great place"

Reviewed on Oct 7, 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
$164 nightly
The price is $201 total per night from Nov 2 to Nov 3
$201 total
Nov 2 - Nov 3
Total with taxes and fees
8.2/10 Very Good! (12,605 reviews)
"Small but clean room. Great staff. Shopping all around the property."

Reviewed on Oct 7, 2025

Chelsea Hotel, Toronto
Toronto Don Valley Hotel and Suites

Toronto Don Valley Hotel and Suites

3.5 out of 5
175 Wynford Drive, Toronto, ON
$103 nightly
The price is $126 total per night from Oct 9 to Oct 10
$126 total
Oct 9 - Oct 10
Total with taxes and fees
7.4/10 Good! (5,989 reviews)
"Clean room. Lots of bath supplies"

Reviewed on Oct 7, 2025

Toronto Don Valley Hotel and Suites
See all 4,179 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.

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 $1,277 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

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.