Pickering Holidays from NZ$2,530
Book a Hotel + Flight or Car together to unlock savings
The Latest Pickering Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Sterling Inn & Spa - an Ontario's Finest Inn
Clifton Hill
NZ$2,838
per person
22 Oct - 25 Oct
found 1 day ago
Return flight included
Auckland (AKL) to Toronto (YYZ)
9.6/10 Exceptional! (2,495 reviews)
Loved this hotel! The housekeeping crew did such a great job. Breakfast in bed was a wonderful touch, and the food was delicious. It’s a quick walk to all the main attractions. Our room was large, and we loved the steam shower and fireplace. Highly recommend!
Reviewed on 20 Sept 2026
Cannery Lofts Niagara
Clifton Hill
NZ$2,613
per person
22 Oct - 25 Oct
found 1 day ago
Return flight included
Auckland (AKL) to Toronto (YYZ)
9.6/10 Exceptional! (1,144 reviews)
The Cannery Lofts are a modern and cool hotel alternative. Minutes walk/drive from the main strip but far away enough that the area around the lofts is very quiet.
The front desk staff was friendly and profession. The room was spacious and clean.
I'd definitely recommend and stay here again.
Reviewed on 21 Sept 2026
South Landing Inn Niagara on the Lake
Queenston
NZ$2,811
per person
22 Oct - 25 Oct
found 1 day ago
Return flight included
Auckland (AKL) to Toronto (YYZ)
9.8/10 Exceptional! (127 reviews)
We booked this property in June and we were excited about our upcoming stay. We read the reviews, travel sites and blogs all commenting on the included amazing Continental breakfast. Our confirmation email also confirmed this was included. We were extremely disappointed when we arrived that this was no longer offered and that instead we were able to get “20% off breakfast at their sister property-something they would further profit from. We never once received an email or phone call prior to our arrival reflecting this change and nor was our price adjusted. The check-in on site person said she would let manager know our concern and she never got back to us. I also sent an email to the reservation manager/Sweet Water Property management while we were there and never received a reply. We would have stayed somewhere else had we known of this change ahead of time. We travel a great deal in North America and Europe in these type of Boutique Inns and have never had this happen. As well travel blogs and sites have recently reviewed this property saying they are a Bed and Breakfast and have an amazing inclusive breakfast?! The onsite person upon checkin tried to pass blame to Expedia and after calling them it is clearly evident it falls with the property. We are still waiting for a response to our concern from the property. As well, there is still a picture on the sites homepage of the breakfast. Will not stay again or recommend mostly due to lack of communication.
Reviewed on 17 Sept 2026
Our guide on where to stay in Pickering
Find the best Pickering areas and neighborhoods for the activities you enjoy most. Learn more about Pickering
Lamoreaux
Lamoreaux might not have many top sights, but Pickering Casino Resort and Herongate Barn Theatre are two attractions nearby that you can check out.
Bay Ridges
2 out of top 10 points of interest in this area
If you're spending some time in Bay Ridges, Lake Ontario and Beachfront Park are top sights worth seeing.
West Shore
While visiting West Shore, you might make a stop by sights like Lake Ontario and Petticoat Creek Conservation Area.
Liverpool
Though Liverpool may not have many top sights, you can venture to the surrounding area to see attractions like Toronto Zoo and Pickering Casino Resort.
City Centre
2 out of top 10 points of interest in this area
While you're in City Centre, take in top sights like Pickering Town Centre and jump on the metro at Pickering Station to see more of the city.
Pickering Holiday
Our pick of the best Pickering Hotel Deals
Pickering Casino Resort Hotel
888 Durham Live Ave Pickering ON
9/10 Wonderful! (5,018 reviews)
"There was Pickering and long wait to get in. The tub to unplug the water is broken, not enough towels and body wash pump was broken. Restaurants were closed with the exception of sun express restaurant. I get it there was no staff, but reception was good and they did maintain the cleanliness of the ..."
Reviewed on 20 Sept 2026
Toronto Don Valley Hotel and Suites
175 Wynford Drive Toronto ON
NZ$217
22 Oct - 23 Oct
includes taxes & fees
7.8/10 Good! (7,001 reviews)
"Facility looks dated compared to when I stayed years ago as a Holiday Inn. The blind to keep early morning sun out has numerous holes in it and should be replaced. The price was right compared to other hotels in Toronto. Good location to highway."
Reviewed on 21 Sept 2026
Chelsea Hotel, Toronto
33 Gerrard St W Toronto ON
Fully refundableReserve now, pay when you stay
NZ$317
12 Oct - 13 Oct
includes taxes & fees
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.
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.
Deer Creek North Golf Course
8.6/10 (7 reviews)
This championship golf course features three distinct nine-hole layouts with strategic challenges and undulating greens. Enjoy a round on meticulously maintained fairways before relaxing at Jerry's Taphouse afterwards.
Glen Cedars Golf Club
7.4/10 (6 reviews)
This parkland-style course offers strategic play through mature tree-lined fairways and rolling terrain. Book a morning tee time for the best experience on this challenging yet scenic 18-hole layout.
Beachfront Park
Why not spend a lazy afternoon at Beachfront Park during your trip to Pickering? Stroll along the lakeside or visit the shops in this family-friendly area.
Millennium Square
Millennium Square provides stunning Lake Ontario views and serves as a community gathering spot. Enjoy Thursday Night Summer Concerts or monthly public star parties for a magical lakeside experience.
Cineplex Cinemas Pickering
This upscale cinema offers premium film experiences with VIP auditoriums featuring reclining seats and in-seat dining. Enjoy the adults-only lounge with craft cocktails before watching the latest blockbusters.
Chestnut Hill Developments Recreation Complex
Enjoy an outing to Chestnut Hill Developments Recreation Complex during your stay in Pickering.
Petticoat Creek Conservation Area
You can take time to visit Petticoat Creek Conservation Area during your travels to Pickering.
What to do in Pickering
Premier Sushi-Making Class in Toronto (Includes 5-Course Meal)
NZ$158
per adult
From Toronto: Small Group 4-Day Eastern Canada Tour
NZ$1,860
per adult
Frequently asked questions
How much does a Pickering holiday package cost?
Offering great value package deals from NZ$2,530 on Expedia, you'll be thrilled with how little a holiday 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 typically find lower rates and greater availability in January, February and March. Check out our cheap Pickering holiday packages and you could score some excellent off-season deals.
How many days is enough for Pickering?
The ideal duration of your Pickering holiday depends on what you'd like to do. Usually, a few days to a week will give you time to visit all the leading sights and explore 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 travelling on a weekday, when prices are often lower.
Is it cheaper to book a Pickering holiday as a package?
Expedia holiday 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 holiday by choosing your preferred type of stay, airline and car class.
When to book a holiday 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 travelling on a whim.
How to plan a trip to Pickering?
- Pick your dates: What you want to do in Pickering and your favourite season will help you decide when to go.
- Calculate your budget: Make sure you have enough money to pay for everything from food and transportation to experiences and flights. Your accommodation will probably be the biggest expense during your trip to Pickering.
- Determine how many days away: Start by listing all the activities and sights you'd like to experience in Pickering. Then, estimate how long you'll need at each, including any travel time.
- Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to find a Pickering holiday 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.
