Pickering Vacations from $713

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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.
One King West Hotel & Residence

One King West Hotel & Residence

4 out of 5
Downtown Toronto
Save 100% on your flight
Price was $1,076, price is now $713 per person
$713
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
9.4/10 Exceptional! (8,228 reviews)
It was just beautiful. The historic aspect that have been preserved were amazing! Location was perfect....for everything!

Reviewed on Aug 6, 2026

Hotel Riu Plaza Toronto

Hotel Riu Plaza Toronto

4 out of 5
Downtown Toronto
Save 100% on your flight
Price was $1,484, price is now $933 per person
$933
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
9.4/10 Exceptional! (4,215 reviews)
A spectacular stay at a prime hotel in a great location in Toronto. Rooms super clean and comfy and the staff were friendly and helpful. Breakfast buffet was amazing with a wide variety of options for food. Even though it was busy every morning, the staff were organised and thorough

Reviewed on Aug 5, 2026

1 Hotel Toronto

1 Hotel Toronto

5 out of 5
Downtown Toronto
Save 100% on your flight
Price was $2,570, price is now $1,632 per person
$1,632
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
9.6/10 Exceptional! (773 reviews)

Four Seasons Hotel Toronto

Four Seasons Hotel Toronto

5 out of 5
Old Toronto
Price was $1,977, price is now $1,293 per person
$1,293
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
9.6/10 Exceptional! (991 reviews)
Wonderful hotel, very relaxing. Thanks.

Reviewed on Aug 4, 2026

Town Inn Suites Hotel

Town Inn Suites Hotel

3.5 out of 5
Downtown Toronto
Save 100% on your flight
Price was $1,076, price is now $719 per person
$719
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
8.6/10 Excellent! (3,888 reviews)

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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.
See properties

What to do in Pickering

Premier Sushi-Making Class in Toronto

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

$91
per adult
Premier Sushi-Making Class in Toronto (Includes 5-Course Meal)
3 Day Eastern Canada Tour Toronto Montreal Quebec and Ottawa

3 Day Eastern Canada Tour Toronto Montreal Quebec and Ottawa

$568
per adult
3 Day Eastern Canada Tour Toronto Montreal Quebec and Ottawa
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
$111 nightly
The price is $131 total per night from Sep 1 to Sep 2
$131 total
Sep 1 - Sep 2
Total with taxes and fees
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
$157 nightly
The price is $188 total per night from Sep 1 to Sep 2
$188 total
Sep 1 - Sep 2
Total with taxes and fees
Chelsea Hotel, Toronto
Fairmont Royal York

Fairmont Royal York

4 out of 5
100 Front St West Toronto ON
Fully refundableReserve now, pay when you stay
$212 nightly
The price is $254 total per night from Aug 30 to Aug 31
$254 total
Aug 30 - Aug 31
Total with taxes and fees
Fairmont Royal York
See all 5,515 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 $713 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.