Pickering Vacations from $364

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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.
The Laundry Rooms Gaslight Cambridge

The Laundry Rooms Gaslight Cambridge

3 out of 5
Save 100% on your flight
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Miami (MIA) to Toronto (YYZ)
9.8/10 Exceptional! (373 reviews)
A great property close to all the expected ammenities. The staff were above board and totally helpful. Will gladly stay again.

Reviewed on Jul 29, 2025

151 Dan Leckie Way

151 Dan Leckie Way

2.5 out of 5
Downtown Toronto
Save 100% on your flight
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Miami (MIA) to Toronto (YYZ)
9.4/10 Exceptional! (227 reviews)
I can’t rate this property as we did not stay there. They switched us property because of plumbing issues. For the property that we did stay at, the futon couch was broken and all bended. We put the mattress on the floor so we could use it as a bed. One of the bedrooms was way to tall for a rental property. There was 2 boxsprings and a mattress. The only seating there was, were barstools and bar height flimsy chairs. We had to be in all different rooms when we were at the Condo. The location was good.

Reviewed on Jul 31, 2025

GLOBALSTAY. Modern Downtown Apartments

GLOBALSTAY. Modern Downtown Apartments

4 out of 5
Downtown Toronto
Save 100% on your flight
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Miami (MIA) to Toronto (YYZ)
7.8/10 Good! (264 reviews)
Convenient and clean

Reviewed on Jul 30, 2025

GLOBALSTAY. Elegant Downtown Apartments

GLOBALSTAY. Elegant Downtown Apartments

4 out of 5
Downtown Toronto
Save 100% on your flight
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Miami (MIA) to Toronto (YYZ)
7.2/10 Good! (340 reviews)
You get what you pay for. This is not a 5 star property but it was 1/5 of the cost of a hotel for a family of 5 in Downtown Toronto. This is equivalent to an air bnb. Check in is done via email and over the phone. I checked out on Sunday morning and received my deposit back exactly 7 days later via PayPal with no hassle. The unit was not the one in the picture and had been flooded in the past and never repaired. The floor was damaged and the baseboards were swelling. The bed sheets were clean and the A/C worked

Reviewed on Jul 25, 2025

1 Hotel Toronto

1 Hotel Toronto

5 out of 5
Downtown Toronto
Save 100% on your flight
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Toronto (YYZ)
9.4/10 Exceptional! (541 reviews)
Fantastic overall experience. Will be back.

Reviewed on Jul 22, 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

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
$103 nightly
The price is $121 total per night from Aug 10 to Aug 11
$121 total
Aug 10 - Aug 11
Total includes taxes and fees
8.8/10 Excellent! (3,021 reviews)
"Jcjk"

Reviewed on Jul 30, 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
$141 nightly
The price is $173 total per night from Aug 4 to Aug 5
$173 total
Aug 4 - Aug 5
Total includes taxes and fees
8.2/10 Very Good! (11,727 reviews)
"OK"

Reviewed on Jul 30, 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
$110 nightly
The price is $135 total per night from Aug 4 to Aug 5
$135 total
Aug 4 - Aug 5
Total includes taxes and fees
7.4/10 Good! (5,852 reviews)
"Staff was very accommodating and pleasant (front desk, store and restaurant) Washroom outside the bar was very dirty Outside clearly shows no smoking under the roof of the parking entrance by the front door, significant amount of smoking happening"

Reviewed on Jul 29, 2025

Toronto Don Valley Hotel and Suites
See all 4,112 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.

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Frequently asked questions

How much does a Pickering vacation package cost?
Offering great value package deals from $364 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.

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