Pickering Vacations from $566

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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
Price was $793, price is now $566 per person
$566
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
9.4/10 Exceptional! (8,048 reviews)
Great location, price and space

Reviewed on Jul 8, 2026

Hotel Riu Plaza Toronto

Hotel Riu Plaza Toronto

4 out of 5
Downtown Toronto
Price was $1,378, price is now $880 per person
$880
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
9.4/10 Exceptional! (3,874 reviews)

1 Hotel Toronto

1 Hotel Toronto

5 out of 5
Downtown Toronto
Price was $1,972, price is now $1,308 per person
$1,308
per person
Aug 7 - Aug 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
9.6/10 Exceptional! (751 reviews)
Great hotel, great staff, great front staff, good food.

Reviewed on Jul 5, 2026

Finlay House Bed and Breakfast Niagara - on - the - Lake

Finlay House Bed and Breakfast Niagara - on - the - Lake

3.5 out of 5
Old Town Historic District
Price was $1,120, price is now $754 per person
$754
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Toronto (YYZ)
9.4/10 Exceptional! (238 reviews)
We had a wonderful stay & Woolf he happy to stay again. Yvonne was a gracious host, serving a lovely hot breakfast each morning. I was traveling with my aunt who had some medically related needs and Yvonne made it clear she was there to help, gave us extra supplies and towels and made us feel so very welcome. She also shared her local knowledge of the area. The inn itself was recently redecorated with lovely furnishings, art, and beautiful wallpapers. Our room (Bernard Shaw Room) was spacious and the bed was so comfortable! My aunt and I shared the oversized king that has a memory foam mattress which prevents one from noticing movement of the other - we slept like rocks! The only improvement I might suggest would be better internet connection, but I wasn’t there to work so it was okay. Beautifully done, quaint/updated, comfortable, great breakfasts, excellent host!

Reviewed on Jun 26, 2026

Modern Lillian Street Condos Midtown Toronto

Modern Lillian Street Condos Midtown Toronto

4 out of 5
Old Toronto
Save 100% on your flight
Price was $850, price is now $622 per person
$622
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Miami (MIA) to Toronto (YYZ)
8.4/10 Very Good! (301 reviews)
Very nice location, everything was so clean and well equipped!

Reviewed on Jun 30, 2026

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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

From Toronto: 5-Day Eastern Canada Small-Group Tour

Soccer Fans 2026: From Toronto 5-Day Eastern Canada Small-Group Tour

$1,451
per adult
Soccer Fans 2026: From Toronto 5-Day Eastern Canada Small-Group Tour
From Toronto: Small Group 5-Day Eastern Canada Tour

From Toronto: Small Group 4-Day Eastern Canada Tour

$1,112
per adult
From Toronto: Small Group 4-Day Eastern Canada Tour
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
$100 nightly
The price is $118 total per night from Jul 13 to Jul 14
$118 total
Jul 13 - Jul 14
Total with taxes and fees
9/10 Wonderful! (4,897 reviews)
"Hôtel luxueux. Personnel très accueillant et aimable. Chambre très propre"

Reviewed on Jul 8, 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
$143 nightly
The price is $175 total per night from Jul 12 to Jul 13
$175 total
Jul 12 - Jul 13
Total with taxes and fees
9/10 Wonderful! (438 reviews)
"Great stay"

Reviewed on Jul 8, 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 refundableReserve now, pay when you stay
$132 nightly
The price is $159 total per night from Aug 3 to Aug 4
$159 total
Aug 3 - Aug 4
Total with taxes and fees
8.6/10 Excellent! (6,100 reviews)
"Great location"

Reviewed on Jul 8, 2026

Holiday Inn Toronto Downtown Centre by IHG
See all 5,402 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 $566 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.