Pickering Vacation Packages

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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!

Top Pickering Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Great Blue Heron Hotel

Great Blue Heron Hotel

4 out of 5
per person
Aug 11 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Toronto (YTO)
9/10 Wonderful! (592 reviews)
Quiet peaceful with good service.

Reviewed on Jul. 1, 2025

1 Hotel Toronto

1 Hotel Toronto

5 out of 5
Downtown Toronto
Save 100% on your flight
per person
Sep 7 - Sep 10
found 22 hours ago
Roundtrip flight included
Vancouver (YVR) to Toronto (YYZ)
9.4/10 Exceptional! (526 reviews)
This was a special occasion for my daughter and I. It could not have been any better. She is really into sustainability and is an environmentalist. We particularly appreciate the knowledge of your staff about your establishment. Not to mention how friendly and personable they are.

Reviewed on Jun. 30, 2025

Vine Ridge Resort

Vine Ridge Resort

2.5 out of 5
Save 100% on your flight
per person
Aug 24 - Aug 31
found 22 hours ago
Roundtrip flight included
Vancouver (YVR) to Toronto (YYZ)
8.6/10 Excellent! (77 reviews)
Wonderful stay! Very close to both Niagara on the Lake and Niagara Falls. Cottage was new and clean, staff were extremely friendly, and the kids had fun. We could bbq and have a campfire, you control the A/C, tv was a smart tv which is better than hotels ;)

Reviewed on Jun. 1, 2025

Kent Motel Niagara on the Lake

Kent Motel Niagara on the Lake

2.5 out of 5
Queenston
Save 100% on your flight
per person
Sep 9 - Sep 15
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Toronto (YYZ)
9.4/10 Exceptional! (203 reviews)
We love the Kent Motel; every room is unique and eclectic and the croissants and coffee in the bake shop downstairs to die for! Quiet neighborhood, but convenient to the Falls and Niagara-on-the-Lake, with great restaurants and historic sites very nearby. This is our favorite place to stay in the area, and we say that as frequent visitors to Niagara who have tried a significant number of accommodations in the area!

Reviewed on Jun. 18, 2025

The Laundry Rooms Gaslight Cambridge

The Laundry Rooms Gaslight Cambridge

3 out of 5
Save 100% on your flight
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Toronto (YYZ)
9.8/10 Exceptional! (363 reviews)
Awesome location, incredibly clean and spacious with luxurious toiletries and no details overlooked.

Reviewed on Jun. 29, 2025

Ready to book your vacation to Pickering?

 

Choose your dates

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
The price is CA $135 per night from Jul 6 to Jul 7
CA $135
CA $170 total
Jul 6 - Jul 7
includes taxes & fees
8.8/10 Excellent! (2,823 reviews)
"Got an upgrade when we arrived late. Rooms are always nice. Parking is easy. Having the casino and some food options within the hotel is always a plus. Pricing is always competitive but we have come to prefer paying a little extra to stay here if we have to."

Reviewed on Jul. 1, 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
The price is CA $195 per night from Jul 13 to Jul 14
CA $195
CA $239 total
Jul 13 - Jul 14
includes taxes & fees
8.2/10 Very Good! (11,504 reviews)
"Excellent for everything from cleanliness high five to room attendant, front desk was very helpful, friendly and accommodating Good Job to all!"

Reviewed on Jun. 30, 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
The price is CA $237 per night from Jul 13 to Jul 14
CA $237
CA $291 total
Jul 13 - Jul 14
includes taxes & fees
8.4/10 Very Good! (4,229 reviews)
"Arriving late the staff was so helpful."

Reviewed on Jul. 1, 2025

Holiday Inn Toronto Downtown Centre by IHG
See all 4,138 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Pickering vacation package cost?
Offering excellent value package deals from CA $633 on Expedia, you'll be surprised at how little a vacation to Pickering costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Pickering?
January, February and March are the best times to look for cheap Pickering vacation packages. Opting to travel in quieter periods means you can typically find lower prices on flights and hotels.
How many days is enough for Pickering?
With a well-organized travel plan, you can easily tick off the top Pickering sights in a handful of days. But if you'd like to venture off the beaten track or take day trips, consider booking your Pickering vacation for longer.
How to find the best Pickering package deals?
Finding a cheap Pickering package deal is easy with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most wallet-friendly Pickering package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Pickering vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging stays and flights individually. Better still, you can personalize your Pickering trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
How to plan a trip to Pickering?

  1. Choose when to go: Check your calendar and get your bags packed. Your favourite season and the activities on offer will also help you decide when to vacation in Pickering.
  2. Budget wisely: Besides the cost of your hotel, you should consider other expenses too. These include transportation, food and flights. Also, put aside some extra funds for unexpected costs that may crop up during your trip to Pickering.
  3. Decide how long to go for: Now that you're up to speed on Pickering, you can figure out the right length of your break. Put together a rough plan and allocate enough time to get through everything on your must-do list.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to choose a Pickering vacation package that brings all your bookings together.

Discover the most popular places to visit in Pickering

Deer Creek North Golf Course

Enjoy a round of golf in Pickering at Deer Creek North Golf Course. You can attend a sporting event while in the area.

Deer Creek North Golf Course

Herongate Barn Theatre

You can get tickets for a performance at Herongate Barn Theatre on your trip to Pickering. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Herongate Barn Theatre

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

Exhiliirate your senses

Exhilarating 120km Aerial Tour of Toronto with iflyTOTO

CA $125
per adult
Exhilarating 120km Aerial Tour of Toronto with iflyTOTO
Small Group: Niagara Falls Full-Day Tour from Toronto

Small Group: Niagara Falls Full-Day Tour from Toronto

CA $89
per adult
Small Group: Niagara Falls Full-Day Tour from Toronto
Pamper yourself

Toronto Aerial Tour with Niagara Winery Tasting Tour with iflyTOTO

CA $310
per adult
Toronto Aerial Tour with Niagara Winery Tasting Tour with iflyTOTO
See all activities in Pickering
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.