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 Waterside Inn

The Waterside Inn

3.5 out of 5
Port Credit
Save 100% on your flight
per person
Oct 3 - Oct 9
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Toronto (YYZ)
8.4/10 Very Good! (1,003 reviews)
The location of this hotel is great. Being right across the street from the lake with easy walks to lakefront parks and restaurants, but the hotel itself is tired and lacks amenities. Our room had a wonderful balcony, but no furniture on it to sit out there and enjoy. There was a coffee maker in the room, but only powdered creamer, no real cream; no little shop to get juice or snacks. I never saw a vending machine. Hallways had that stale smoke smell like the carpeting hadn't been cleaned since smoking was allowed. No shuttle to airport.

Reviewed on Jul. 15, 2025

Town Inn Suites Hotel

Town Inn Suites Hotel

3.5 out of 5
Downtown Toronto
Save 100% on your flight
per person
Oct 3 - Oct 9
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Toronto (YYZ)
8.4/10 Very Good! (3,107 reviews)
The parking is 40$/night and not included.. I chose to park outside but read the signs wrong and got a 190$ticket... I thought parking was included with description . The rooms are EXTREMELY spacious with all amenities

Reviewed on Jul. 15, 2025

GLOBALSTAY Modern Lillian St Apartments

GLOBALSTAY Modern Lillian St Apartments

4.5 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)
7.2/10 Good! (88 reviews)
Our stay was pretty good. very quiet and easy access.

Reviewed on Jul. 13, 2025

GLOBALSTAY. Maple Leaf Square

GLOBALSTAY. Maple Leaf Square

3.5 out of 5
Downtown Toronto
Save 100% on your flight
per person
Sep 30 - Oct 5
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Toronto (YYZ)
7.6/10 Good! (424 reviews)
Close proximity to everything downtown. Easy check in, however they require a 200$ paypal deposit which they return 7 days after check out. I did have to contact and paypal invoice them to recieve mine back.

Reviewed on May 22, 2025

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
Aug 27 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Toronto (YYZ)
9.2/10 Wonderful! (307 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

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 20 to Jul 21
CA $135
CA $170 total
Jul 20 - Jul 21
includes taxes & fees
8.8/10 Excellent! (2,898 reviews)
"Amazing"

Reviewed on Jul. 13, 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 $212 per night from Aug 4 to Aug 5
CA $212
CA $260 total
Aug 4 - Aug 5
includes taxes & fees
8.2/10 Very Good! (11,635 reviews)
"Very good hotel and great location !"

Reviewed on Jul. 15, 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 $152 per night from Jul 16 to Jul 17
CA $152
CA $186 total
Jul 16 - Jul 17
includes taxes & fees
7.2/10 Good! (5,801 reviews)
"Superior room very nice, spacious, fridge nice balcony, coffee machine so so and bathroom was not renovated."

Reviewed on Jul. 15, 2025

Toronto Don Valley Hotel and Suites
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

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 $769 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.