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.
The Laundry Rooms Station Park Kitchener

The Laundry Rooms Station Park Kitchener

2 out of 5
K-W Hospital
Save 100% on your flight
per person
Sep 13 - Sep 20
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Toronto (YYZ)
9.2/10 Wonderful! (305 reviews)
The Laundry Rooms is a new experience for me, and I am happy to say I am a huge fan! The price point was excellent considering you got so much more than other hotel rooms in the area that were so much more money! It was like a fully stock apartment! Can’t wait to find an excuse to stay at this one or another one sometime soon, and I’ll be recommending it to family and friends!

Reviewed on Jul. 11, 2025

Vine Ridge Resort

Vine Ridge Resort

2.5 out of 5
Save 100% on your flight
per person
Aug 17 - Aug 24
found 10 hours ago
Roundtrip flight included
Edmonton (YEG) 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

GLOBALSTAY Luxury Townhouse in Downtown Toronto

GLOBALSTAY Luxury Townhouse in Downtown Toronto

3.5 out of 5
Old Toronto
Save 100% on your flight
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Toronto (YYZ)
8.8/10 Excellent! (5 reviews)
I, in fact my whole family loves to stay at this property.Easy access to whole down town.People who buy City Pass for Toronto attractions accept Toronto Zoo all attractions are near by from this property. I feel like I m leaving in my own house with family and did this tour.

Reviewed on Jul. 4, 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 15 - Sep 20
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Toronto (YYZ)
9.4/10 Exceptional! (203 reviews)
This property was amazing! It was close to the main strip of Niagara-in-the-Lake and so convenient! There is plenty of parking and great lounge for a bite and drink.

Reviewed on Jul. 6, 2025

Old Mill Toronto

Old Mill Toronto

4 out of 5
Etobicoke
Save 100% on your flight
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Toronto (YYZ)
9.2/10 Wonderful! (1,020 reviews)
A great place to stay. An oasis in a big city.

Reviewed on Jul. 9, 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 13 to Jul 14
CA $135
CA $170 total
Jul 13 - Jul 14
includes taxes & fees
8.8/10 Excellent! (2,877 reviews)
"Great hotel if you need a place to stay in the area."

Reviewed on Jul. 10, 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 $229 per night from Aug 4 to Aug 5
CA $229
CA $280 total
Aug 4 - Aug 5
includes taxes & fees
8.2/10 Very Good! (11,560 reviews)
"Excellent rooms and service. Great internet connection and great dowtown location. Close to everything i.e. bars restaurants, shops eaton centre are a mins. walk away. Reasonably priced especially for being in the dt core."

Reviewed on Jul. 11, 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
The price is CA $169 per night from Jul 13 to Jul 14
CA $169
CA $207 total
Jul 13 - Jul 14
includes taxes & fees
7.2/10 Good! (5,758 reviews)
"."

Reviewed on Jul. 11, 2025

Toronto Don Valley Hotel and Suites
See all 4,149 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

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

Millennium Square

You can find out about the history of Pickering with a stop at Millennium Square. Stroll along the lakeside or visit the shops in this family-friendly area.

Millennium Square

What to do in Pickering

Beach day Sandbanks Provincial Park

Beach day Sandbanks Provincial Park

CA $127
per adult
Beach day Sandbanks Provincial Park
See all activities in Pickering

Frequently asked questions

How much does a Pickering vacation package cost?
Offering excellent value package deals from CA $667 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.

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