Title: Pickering Vacation Packages & Trips 2025/2026 from CA $863 | Expedia.ca [Pickering Travel Guide](https://expedia.ca/Pickering.dx9546)[Hotels in Pickering](https://expedia.ca/Pickering-Hotels.d9546.Travel-Guide-Hotels)[Vacation Rentals in Pickering](https://expedia.ca/Pickering-Vacation-Rentals.d9546.Travel-Guide-VacationRentals)[Flights to Pickering](https://expedia.ca/Cheap-Flights-To-Pickering.d9546.Travel-Guide-Flights)[Things to do in Pickering](https://expedia.ca/Things-To-Do-In-Pickering.d9546.Travel-Guide-Activities)[Pickering Car Rentals](https://expedia.ca/Car-Rentals-In-Pickering.d9546.Car-Rental-Guide) ![](https://images.trvl-media.com/place/9546/c76ef984-634c-45ee-a5b7-b2bf4a782a7b.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Pickering Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Eric & Kristy's Adventures - ## Plan, book, travel with confidence ### Better together Save up to CA $1,096 when you book a flight and hotel together\* ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package ### Rest easy Plan, book, and manage your trip all in one place #### 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](https://www.expedia.ca/Rotary-Park-Ajax.d553248621532865063.Vacation-Attraction), [Herongate Barn Theatre](https://www.expedia.ca/Herongate-Barn-Theatre-Pickering.d553248621532865061.Vacation-Attraction) and [Annandale Golf and Country Club](https://www.expedia.ca/Annandale-Golf-And-Country-Club-Pickering.d553248621532865065.Vacation-Attraction). 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. ![GLOBALSTAY Modern Lillian St Apartments](https://images.trvl-media.com/lodging/94000000/93530000/93526700/93526630/98b8bb96_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### GLOBALSTAY Modern Lillian St Apartments Old Toronto CA $863 per person Nov 22 - Nov 28 found 1 day ago Roundtrip flight included Winnipeg (YWG) to Toronto (YYZ) 7.2/10 Good! (109 reviews) It was a nice apartment & pool area. Reviewed on Sep 15, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-22/2025-11-28/?FromAirport=YWG&Destination=YYZ&NumRoom=1&NumAdult=2&NumChild=0&hotelId=93526630&paandie=true&dealMarker=qgzs5DK0AdLEKNM1gn0bBMzB9en7CGGOvAoHEze1nDFn6d7tzfbau7RHW5t3QocG) ![Woodbourne Inn](https://images.trvl-media.com/lodging/15000000/14640000/14634700/14634695/cea179d4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Woodbourne Inn St. Davids CA $904 per person Nov 24 - Dec 1 found 1 day ago Roundtrip flight included Edmonton (YEG) to Toronto (YYZ) 9.8/10 Exceptional! (495 reviews) We, mother and daughter from Japan enjoyed every minute of our stay at Woodbourne Inn. Warm welcome, beautiful place, great breakfast, and so on. A winery with an excellent restaurant is within walking distance. Reviewed on Aug 24, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-24/2025-12-01/?FromAirport=YEG&Destination=YYZ&NumRoom=1&NumAdult=2&NumChild=0&hotelId=14634695&paandie=true&dealMarker=qgzs5DK0AdLEKNM1gn0bBOY9MJowLQYvAwNzVJgV4iXzspqxX9tLPWr9H4go8N0d) ![mehri suites](https://images.trvl-media.com/lodging/120000000/119230000/119221900/119221849/3ddb1613_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### mehri suites Downtown Toronto CA $2,334 per person Nov 24 - Nov 30 found 1 day ago Roundtrip flight included Edmonton (YEG) to Toronto (YYZ) 10/10 Exceptional! (6 reviews) 5 minutes to airport o the hotel shuttle. Reviewed on Sep 11, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-24/2025-11-30/?FromAirport=YEG&Destination=YYZ&NumRoom=1&NumAdult=2&NumChild=0&hotelId=119221849&paandie=true&dealMarker=ig2A2rIFihOxWYLgoRpK8se4XpGJHB30Ys3LG1Meu1ffMMc-phV3pdTtEJ_QvAXK) ![Cityplace Executive Suites](https://images.trvl-media.com/lodging/111000000/110010000/110007100/110007069/44c34fd7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cityplace Executive Suites Downtown Toronto CA $893 per person Nov 24 - Nov 30 found 6 hours ago Roundtrip flight included Edmonton (YEG) to Toronto (YYZ) 8.2/10 Very Good! (23 reviews) The location for what was needed for this trip was very good. The Condo building was nice, but quite busy as people were arriving and departing daily. We had the unfortunate experience as one of elevators were down for two days. The condo we rented was nice however the beds were to low on the floor. There were no wash cloths,just towels. Kitchen had no drying towels or dish cloths. Had a coffee maker with filters but no Coffee. Maybe a Keurig coffee maker would be better for renter to purchase type of coffee. Could not adjust temperature. The worst part for us was getting access to picking up the keys to the condo. Our opinion is the owner needs to have a different system and or location for key pick-up. Overall 4 stars Reviewed on Sep 12, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-24/2025-11-30/?FromAirport=YEG&Destination=YYZ&NumRoom=1&NumAdult=2&NumChild=0&hotelId=110007069&paandie=true&dealMarker=6ftc-nccNdmICe2oTNOgKSgRSzf8fZbt6cSRzq3kVrxnFXzt9szky6_g94c9kfme) ![1 Hotel Toronto](https://images.trvl-media.com/lodging/3000000/2930000/2920200/2920159/23374630_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel Toronto Downtown Toronto CA $1,162 per person Dec 11 - Dec 14 found 1 day ago Roundtrip flight included Edmonton (YEG) to Toronto (YYZ) 9.4/10 Exceptional! (595 reviews) Clean room, nice restaurants and polite staff. Reviewed on Sep 8, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-11/2025-12-14/?FromAirport=YEG&Destination=YYZ&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2920159&paandie=true&dealMarker=5we3j8KC6OqTIzByFJ8BVsHw_bvjm5X0V_O0eEWCRsSfDslf8oJKetyCBCrzc3NA) ## Ready to book your vacation to Pickering? Choose your dates ## Pickering Hotel Deals ![Pickering Casino Resort Hotel](https://images.trvl-media.com/lodging/90000000/89440000/89435800/89435702/bfd9e71e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Pickering Casino Resort Hotel 888 Durham Live Ave, Pickering, ON Fully refundableReserve now, pay when you stay CA $135 CA $170 total Oct 13 - Oct 14 includes taxes & fees 8.8/10 Excellent! (3,329 reviews) "Mohamed was very very helpful with my check-in. He is the on point, helpful, and will make your stay as comfortable as possible." Reviewed on Sep 17, 2025 [](https://expedia.ca/Hotel-Search?startDate=13%2F10%2F2025&endDate=14%2F10%2F2025&selected=89435702&PinnedHotelID=89435702&HadPinnedHotel=true®ionId=9546) ![Chelsea Hotel, Toronto](https://images.trvl-media.com/lodging/1000000/30000/28000/27994/c0edbb5d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Chelsea Hotel, Toronto 33 Gerrard St W, Toronto, ON Fully refundableReserve now, pay when you stay CA $178 CA $218 total Oct 11 - Oct 12 includes taxes & fees 8.2/10 Very Good! (12,453 reviews) "Good gym with a great rooftop view of the city. The Will Street bar and lounge was a great hang. I was there for the film fest and the location was convenient for that as well." Reviewed on Sep 20, 2025 [](https://expedia.ca/Hotel-Search?startDate=11%2F10%2F2025&endDate=12%2F10%2F2025&selected=27994&PinnedHotelID=27994&HadPinnedHotel=true®ionId=9546) ![Holiday Inn Toronto Downtown Centre by IHG](https://images.trvl-media.com/lodging/1000000/30000/26300/26247/f61ea124_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Toronto Downtown Centre by IHG 30 Carlton Street, Toronto, ON Fully refundable CA $227 CA $278 total Sep 28 - Sep 29 includes taxes & fees 8.4/10 Very Good! (4,632 reviews) "Nice hotel" Reviewed on Sep 19, 2025 [](https://expedia.ca/Hotel-Search?startDate=28%2F09%2F2025&endDate=29%2F09%2F2025&selected=26247&PinnedHotelID=26247&HadPinnedHotel=true®ionId=9546) [See all 4,172 properties in Pickering](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=21%2F09%2F2025&endDate=22%2F09%2F2025®ionId=9546) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### 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. [](https://expedia.ca/Deer-Creek-North-Golf-Course-Pickering.d553248621532865069.Vacation-Attraction) #### 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. [](https://expedia.ca/Herongate-Barn-Theatre-Pickering.d553248621532865061.Vacation-Attraction) #### 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. [](https://expedia.ca/Millennium-Square-Pickering.d840870924103405568.Vacation-Attraction) ### What to do in Pickering ![Small Group: Niagara Falls Full-Day Tour from Toronto](https://mediaim.expedia.com/localexpert/50049523/1cb32014-fa16-4e18-8913-9467ab514672.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Small Group: Niagara Falls Full-Day Tour from Toronto CA $89 per adult **100%** of travellers recommend [](https://expedia.ca/things-to-do/small-group-niagara-falls-full-day-tour-from-toronto.a50049523.activity-details) ![Premier Sushi-Making Class in Toronto](https://mediaim.expedia.com/localexpert/50010619/97184e21-f083-40cc-8319-f3f521f11b33.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Premier Sushi-Making Class in Toronto (Includes 5-Course Meal) CA $129 per adult [](https://expedia.ca/things-to-do/premier-sushi-making-class-in-toronto-includes-5-course-meal.a50010619.activity-details) [See all activities in Pickering](https://expedia.ca/things-to-do/search?rid=9546) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental ### Lodging - [5 Star Hotels in Ajax](https://www.expedia.ca/5Star-Ajax-Hotels.s50-0-d6047927.Travel-Guide-Filter-Hotels) - [Apartments in Ajax](https://www.expedia.ca/Ajax-Apartments.d6047927-aaApartments.Travel-Guide-Accommodation) - [B&B in Ajax](https://www.expedia.ca/Ajax-Bed-And-Breakfast.d6047927-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Condo Rentals in Ajax](https://www.expedia.ca/Ajax-Condos.d6047927-aaCondos.Travel-Guide-Accommodation) - [Cottages in Ajax](https://www.expedia.ca/Ajax-Cottages.d6047927-aaCottages.Travel-Guide-Accommodation) - [Best Western Hotels in Ajax](https://www.expedia.ca/Ajax-Hotels-Best-Western.0-0-d6047927--bBestWestern.Travel-Guide-Filter-Hotels) - [Casino Hotels in Ajax](https://www.expedia.ca/Ajax-Hotels-Casino-Hotel.0-0-d6047927-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Ajax](https://www.expedia.ca/Ajax-Hotels-Cheap-Hotels.0-0-d6047927-tCheapHotels.Travel-Guide-Filter-Hotels) - 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[Flights from Toronto](https://www.expedia.ca/lp/flights/178314/flights-from-toronto) - [Flights from Ajax](https://www.expedia.ca/lp/flights/6047927/flights-from-ajax) - [Flights from Delhi (DEL) to Toronto (YYZ)](https://www.expedia.ca/lp/flights/del/yyz/delhi-to-toronto) - [Flights from Edmonton (YEG) to Toronto (YYZ)](https://www.expedia.ca/lp/flights/yeg/yyz/edmonton-to-toronto) - [Flights from Halifax (YHZ) to Toronto (YTO)](https://www.expedia.ca/lp/flights/yhz/yto/halifax-to-toronto) - [Flights from Montreal (YUL) to Toronto (YYZ)](https://www.expedia.ca/lp/flights/yul/yyz/montreal-to-toronto) - [Flights from Vancouver (YVR) to Toronto (YYZ)](https://www.expedia.ca/lp/flights/yvr/yyz/vancouver-to-toronto) - [Flights from Winnipeg (YWG) to Toronto (YYZ)](https://www.expedia.ca/lp/flights/ywg/yyz/winnipeg-to-toronto) - [Flights from Calgary (YYC) to Toronto (YYZ)](https://www.expedia.ca/lp/flights/yyc/yyz/calgary-to-toronto) ### Packages - [Ajax Convention Centre](https://www.expedia.ca/Ajax-Convention-Centre-Ajax.d553248621563220601.Vacation-Attraction) - [Ajax Vacations](https://www.expedia.ca/Ajax.d6047927.Destination-Travel-Guides) - [Visit Ajax](https://www.expedia.ca/Ajax.dx6047927) - [Annandale Golf and Country Club](https://www.expedia.ca/Annandale-Golf-And-Country-Club-Pickering.d553248621532865065.Vacation-Attraction) - [Brooklin Vacations](https://www.expedia.ca/Brooklin.d3000480353.Destination-Travel-Guides) - [Colonel Danforth Park](https://www.expedia.ca/Colonel-Danforth-Park-Scarborough.d553248621532865057.Vacation-Attraction) - [Deer Creek North Golf Course](https://www.expedia.ca/Deer-Creek-North-Golf-Course-Pickering.d553248621532865069.Vacation-Attraction) - [Herongate Barn Theatre](https://www.expedia.ca/Herongate-Barn-Theatre-Pickering.d553248621532865061.Vacation-Attraction) - [Iskcon Scarborough](https://www.expedia.ca/ISKCON-Scarborough-Scarborough.d553248621532865055.Vacation-Attraction) - [Kennedy Commons Mall](https://www.expedia.ca/Kennedy-Commons-Mall-Scarborough.d6219778.Vacation-Attraction) - [Luke Andrews Wood Sculptures](https://www.expedia.ca/Luke-Andrews-Wood-Sculptures-Pickering.d553248621532865085.Vacation-Attraction) - [Markham Museum](https://www.expedia.ca/Markham-Museum-Toronto.d6197111.Vacation-Attraction) - [Markham Pan Am Centre](https://www.expedia.ca/Markham-Pan-Am-Centre-Toronto.d553248621587527600.Vacation-Attraction) - [Markham Village](https://www.expedia.ca/Markham-Village-Toronto.d553248621533087783.Vacation-Attraction) - [Markville Shopping Center](https://www.expedia.ca/Markville-Shopping-Center-Toronto.d6189590.Vacation-Attraction) - [Millennium Square](https://www.expedia.ca/Millennium-Square-Pickering.d840870924103405568.Vacation-Attraction) - [Milne Dam Conservation Park](https://www.expedia.ca/Milne-Dam-Conservation-Park-Toronto.d6189586.Vacation-Attraction) - [Morningside Park](https://www.expedia.ca/Morningside-Park-Scarborough.d6205996.Vacation-Attraction) - [Oshawa Centre](https://www.expedia.ca/Oshawa-Centre-Vanier.d6134361.Vacation-Attraction) - [Pacific Mall](https://www.expedia.ca/Pacific-Mall-Toronto.d6072477.Vacation-Attraction) - [Rotary Park](https://www.expedia.ca/Rotary-Park-Ajax.d553248621532865063.Vacation-Attraction) - [Rouge National Urban Park](https://www.expedia.ca/Rouge-National-Urban-Park-Scarborough.d6072483.Vacation-Attraction) - [Scarborough Town Centre](https://www.expedia.ca/Scarborough-Town-Centre-Scarborough.d6144393.Vacation-Attraction) - [Scarborough Village Vacations](https://www.expedia.ca/Scarborough-Village.d10208.Destination-Travel-Guides) - [Scarborough Vacations](https://www.expedia.ca/Scarborough.d6070427.Destination-Travel-Guides) - [Thomson Memorial Park](https://www.expedia.ca/Thomson-Memorial-Park-Scarborough.d6197109.Vacation-Attraction) - [Visit Downtown Toronto](https://www.expedia.ca/Toronto-Downtown-Toronto.dx6057934) - [Toronto Zoo](https://www.expedia.ca/Toronto-Zoo-Scarborough.d503151.Vacation-Attraction) - [Toronto Vacations](https://www.expedia.ca/Toronto.d178314.Destination-Travel-Guides) - [Veterans' Point Gardens](https://www.expedia.ca/Veterans-Point-Gardens-Ajax.d553248621532865067.Vacation-Attraction) - [Whitby History Museum & Children's Centre](https://www.expedia.ca/Whitby-History-Museum-Childrens-Centre-Whitby.d553248621562268588.Vacation-Attraction) - 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