Pickering Vacations from $456

Book a Hotel + Flight or Car together to unlock savings

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.
Sandman Hotel Oakville

Sandman Hotel Oakville

3.5 out of 5
Save 100% on your flight
Price was $725, price is now $456 per person
$456
per person
Feb 12 - Feb 16
found 1 hour ago
Roundtrip flight included
New York (NYC) to Toronto (YYZ)
17.6/10 Exceptional! (2,188 reviews)
Salim, front desk, was very helpful. Great personnel, but overpriced when considering the rooms and amenities.

Reviewed on Nov 22, 2025

New 3BR Townhouse, Minutes to Niagara Falls and Brock University by GLOBALSTAY

New 3BR Townhouse, Minutes to Niagara Falls and Brock University by GLOBALSTAY

4 out of 5
Save 100% on your flight
Price was $1,028, price is now $646 per person
$646
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip flight included
Nassau (NAS) to Toronto (YYZ)
17.6/10 Exceptional! (25 reviews)
I was happy with everything

Reviewed on Nov 19, 2025

Sandman Hotel Hamilton

Sandman Hotel Hamilton

3.5 out of 5
Lakeley
Price was $736, price is now $465 per person
$465
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Hamilton (YHM)
17.6/10 Exceptional! (1,464 reviews)
Did not go to bar or had breakfast on site

Reviewed on Nov 18, 2025

The Sutton Place Hotel Toronto

The Sutton Place Hotel Toronto

4.5 out of 5
Downtown Toronto
Save 100% on your flight
Price was $906, price is now $575 per person
$575
per person
Feb 13 - Feb 16
found 20 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
19.2/10 Exceptional! (2,505 reviews)
Friendly, helpful team. Lovely spacious rooms. Comfortable bed and great shower. Easy parking for downtown and well situated for walking to restaurants and other downtown attractions. Overall, great value for money

Reviewed on Nov 20, 2025

Harbourfront 2 Bed Suites

Harbourfront 2 Bed Suites

2.5 out of 5
Downtown Toronto
Save 100% on your flight
Price was $996, price is now $636 per person
$636
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
16/10 Exceptional! (127 reviews)
Location with key for us as well as a functioning, kitchen and easy access to BMO field and groceries

Reviewed on Nov 16, 2025

Don't see what you're looking for?
See all available trips from Columbus to Pickering
View all trips

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now

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)

$92
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
$76 nightly
The price is $89 total per night from Dec 1 to Dec 2
$89 total
Dec 1 - Dec 2
Total with taxes and fees
9/10 Wonderful! (3,658 reviews)
Yes clean, and all the staff are very nice

Reviewed on Nov 17, 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
$104 nightly
The price is $127 total per night from Nov 30 to Dec 1
$127 total
Nov 30 - Dec 1
Total with taxes and fees
8.2/10 Very Good! (13,115 reviews)
clean room, tv great . great ammenities

Reviewed on Nov 17, 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
$107 nightly
The price is $131 total per night from Dec 22 to Dec 23
$131 total
Dec 22 - Dec 23
Total with taxes and fees
8.4/10 Very Good! (4,889 reviews)
The breakfast was good, with standard options like fruit, bread, eggs, but also yogurt, cereal, juice, and pastries. However, it was the same thing every day without many options for each item, so I can't say it was excellent. Some employees were not very friendly, while others were okay. The bed ...

Reviewed on Nov 20, 2025

Holiday Inn Toronto Downtown Centre by IHG
See all 4,373 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Pickering vacation package cost?
Offering great value package deals from $456 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.