Pickering Holidays from £935

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Your Pickering Holiday

With plenty of highlights as well as hidden gems, this city is best explored with a Pickering holiday 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 holiday to Pickering to match your travel style, whatever that may be!

The Latest Pickering Holiday Deals

Price found within the past 48 hours. Click for updated prices.
GLOBALSTAY. Charming Yorkville Condos

GLOBALSTAY. Charming Yorkville Condos

4 out of 5
Old Toronto
Save 100% on your flight
per person
5 Sept - 11 Sept
found 4 hours ago
Return flight included
Edinburgh (EDI) to Toronto (YYZ)
7.8/10 Good! (127 reviews)
Everything was great, except the tv did not work during our stay.

Reviewed on 19 Jun 2025

Altitude Suites on Yonge

Altitude Suites on Yonge

4 out of 5
Downtown Toronto
Save 100% on your flight
per person
5 Sept - 11 Sept
found 4 hours ago
Return flight included
Edinburgh (EDI) to Toronto (YYZ)
9/10 Wonderful! (63 reviews)
I like the city view and cleanse of the room

Reviewed on 12 Jun 2025

151 Dan Leckie Way

151 Dan Leckie Way

2.5 out of 5
Downtown Toronto
Save 100% on your flight
per person
4 Aug - 11 Aug
found 16 hours ago
Return direct flight included
Edinburgh (EDI) to Toronto (YYZ)
9.4/10 Exceptional! (225 reviews)
They changed our condo for any uses but was excellent.

Reviewed on 26 Jun 2025

1 Hotel Toronto

1 Hotel Toronto

5 out of 5
Downtown Toronto
Save 100% on your flight
per person
23 Aug - 30 Aug
found 1 day ago
Return direct flight included
London (LHR) to Toronto (YYZ)
9.4/10 Exceptional! (526 reviews)
Amazing service. Would love to stay there again! Room was perfect.

Reviewed on 1 Jul 2025

GLOBALSTAY. Burano Condos in Downtown Toronto

GLOBALSTAY. Burano Condos in Downtown Toronto

3 out of 5
Downtown Toronto
Save 100% on your flight
per person
5 Sept - 11 Sept
found 4 hours ago
Return flight included
Edinburgh (EDI) to Toronto (YYZ)
7.2/10 Good! (59 reviews)
We were looking for a reasonably priced place that was close to downtown, and this satisfied: We were within two blocks of College Station, with a grocery store, two drugstores, and a variety of restaurants also within two blocks. If you like daily turndown service or morning continental breakfasts, this isn't the place for you, but we liked having the condo entirely to ourselves for the entire six-night stay. Our teen slept on the pullout couch, and though he's a picky sleeper, he said it was comfortable. The main bed was also fine. My only real complaint: I was initially told there would be parking available, but closer to the date, they said there wasn't any. However, through SpotHero, I found an inexpensive spot two blocks away, and since the plan was to use public transit the entire time, that worked out fine.

Reviewed on 1 Jul 2025

Downtown Toronto near CN Tower

Downtown Toronto near CN Tower

3 out of 5
Downtown Toronto
Save 100% on your flight
per person
5 Sept - 11 Sept
found 4 hours ago
Return flight included
Edinburgh (EDI) to Toronto (YYZ)
8.4/10 Very Good! (36 reviews)
It had a balcony a decent kitchen and it was clean and the staff were friendly

Reviewed on 20 Jun 2025

Pickering Essential Information

Language
English
Currency
Canadian dollars
Closest Airport
Billy Bishop Toronto City Airport (YTZ)
Population
87,800
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Herongate Barn Theatre, Whitby History Museum & Childrens Centre and Deer Creek North Golf Course

Our pick of the best Pickering Hotel Deals

Pickering Casino Resort Hotel
Pickering Casino Resort Hotel
4 out of 5
888 Durham Live Ave, Pickering, ON
Stay at this 4-star business-friendly hotel in Pickering. Enjoy free Wi-Fi, free parking and 6 restaurants. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (2,815 reviews)
"Good value"

Reviewed on 29 Jun 2025

Pickering Casino Resort Hotel
Chelsea Hotel, Toronto
Chelsea Hotel, Toronto
4 out of 5
33 Gerrard St W, Toronto, ON
Stay at this 4-star eco-certified hotel in Toronto. Enjoy free Wi-Fi, 2 indoor pools and 2 restaurants. Our guests praise the pool and the restaurant in their ...
8.2/10 Very Good! (11,520 reviews)
"Excellent housekeeping staff."

Reviewed on 30 Jun 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
Stay at this 3.5-star eco-certified hotel in Toronto. Enjoy free Wi-Fi, breakfast (surcharge) and a fitness centre. Our guests praise the restaurant and the ...
8.4/10 Very Good! (4,218 reviews)
"A massive hotel. My room was very small with only a little window that faced a dark exterior alcove. The hotel obviously has a lot of guests, so the furniture has dents and marks and needed tending. The dark carpet did not seem clean. There was an extended power failure in the area, which meant I ..."

Reviewed on 29 Jun 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 Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

Why should I book my Pickering holiday with Expedia?
Choose Expedia to plan your next big escape with ease, all in the same place. Our top tip for bagging a fabulous deal on a Pickering retreat? Bundle your flights, accommodation and/or hire car into a package holiday. Then add some exciting tours and activities. Most bookings also come with flexible cancellation policies, so there's no need to worry if you have to switch up your travel itinerary. Round-the-clock assistance with making tweaks to your trip is on-hand via our Customer Service Portal link.
When is the best time of year to holiday in Pickering?
If you enjoy the atmosphere of peak season, head to Pickering in June, July and August. If you prefer a calmer vibe, January, February and October are better times to visit. Organise your escape to Pickering according to what style of holiday you're looking for. January is the coolest time of year, when daytime temperatures average -5ºC. In July, the warmest period, you will experience temperatures of around 21ºC during the day.
What is the top hotel for my holiday in Pickering?
Put your feet up and relax in comfort in Pickering by choosing La Quinta Inn & Suites by Wyndham Oshawa as your gateway to adventure and exploration.
How do I get a cheap holiday to Pickering?
Bundle your bookings with Expedia to save on your next getaway. With over 400 partner airlines and 321,000 properties throughout the world, your Pickering holiday can be tailored exactly to suit your travel style. With all that extra cash, why not include a few exciting tours and activities? It's an easy way to unlock even more savings. Your dream holiday in Pickering is much closer than you thought! Learn more about how you can save money on your holiday when you combine your flight and hotel bookings with Expedia.
What should I do on my Pickering holiday?
There's an almost endless list of things to keep you busy while on a holiday in Pickering. Ajax Convention Centre, Deer Creek North Golf Course, Herongate Barn Theatre and Rotary Park are among this city's leading attractions.
What is the best area to stay in when on holiday in Pickering?
If you're interested in visiting Deer Creek North Golf Course, maximise your time sightseeing and find a place to stay nearby. It's one of the best attractions in Pickering.
Do I need a visa for my Pickering holiday?
Research the latest information on official government websites. Your nationality and whether you're visiting for study, business or leisure will determine if you need a visa for Pickering. Familiarise yourself with the application process, including the required documentation, fees and turnaround times. Finalise your application well in advance to allow plenty of time for processing. Some visas may take several weeks or even months to obtain, depending on the country.
What should I wear on my Pickering holiday?
First, think about the sorts of activities you have planned during your trip to Pickering and bring versatile pieces that you can easily mix and match. For fashion inspiration or information on any dress codes, look up style blogs or relevant social media accounts. Daytime temperatures during January, Pickering's coolest month, average -5ºC. July marks this destination's warmest month when the average temperature reaches 21ºC. Our top tip? Take the guesswork out of what to pack and check the local weather conditions.
What does an Expedia Pickering holiday include?
Hotels, flights and a reliable car for your road trip adventures. Simply select your favourite bundle and get access to incredible deals. Once you've made your booking, add on a few tours and activities and watch your savings grow. When it comes to creating your Pickering getaway, you're in control! Expedia features all sorts of properties, with the most popular in Pickering including private holiday homes and apartments. With Expedia, you'll always enjoy the flexibility and freedom to personalise your holiday however you want.
Does Expedia offer Book Now, Pay Later Pickering holidays?
We do. Expedia has teamed up with online lender Klarna to help you conveniently pay for your trip in instalments. Simply choose the payment plan that suits best during the checkout process and take the stress out of budgeting for your trip. Don't forget to bundle your accommodation, flights and car hire with Expedia to get the biggest bang for your buck. Browse our flexible payment options below:

  • Pay monthly holidays: If paying small amounts each month is what works best for you, Klarna offers just that! Paying in several transactions will make your getaway dreams come true.
  • No-deposit holidays: If not paying upfront for your getaway makes pressing that "book now" button more stress-free, opt for a no-deposit holiday plan from Klarna so that you can Book Now, Pay Later!

Can I choose my airline with a Pickering Expedia holiday?
Yes --- that's the beauty of an Expedia holiday package. You get to choose. We have more than 400 airline partners all over the world, so you have loads of choice when organising your Pickering getaway.

Unmissable things to do in Pickering

Exhiliirate your senses

Exhilarating 120km Aerial Tour of Toronto with iflyTOTO

£67
per adult
Exhilarating 120km Aerial Tour of Toronto with iflyTOTO
Pamper yourself

Toronto Aerial Tour with Niagara Winery Tasting Tour with iflyTOTO

£167
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. Flight-inclusive packages are ATOL protected.