Title: Pickering Vacation Packages & Trips 2025/2026 from CA $706 | 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. ![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 $706 per person Nov 12 - Nov 17 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/2025-11-12/2025-11-17/?FromAirport=YEG&Destination=YYZ&NumRoom=1&NumAdult=2&NumChild=0&hotelId=14634695&paandie=true&dealMarker=3_KnkPWBt-fMsRxjh22jPY1v-o8b_CtP5uJDCxEJcf0XZA00gatB_s3LHp8zbvWL) ![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 $2,238 per person Nov 24 - Nov 30 found 1 day ago Roundtrip flight included Edmonton (YEG) to Toronto (YYZ) 9.4/10 Exceptional! (587 reviews) Clean room, nice restaurants and polite staff. Reviewed on Sep 8, 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=2920159&paandie=true&dealMarker=A_7a3Em_ifmnR2ylryw5LpGh1PXcLk9H9MWGoKlYDnitkjGhF4pI5-Q9ZbFSVvHa) ![The Laundry Rooms Station Park Kitchener](https://images.trvl-media.com/lodging/93000000/92710000/92703200/92703199/c6bf613f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Laundry Rooms Station Park Kitchener K-W Hospital CA $767 per person Oct 20 - Oct 27 found 1 day ago Roundtrip flight included Edmonton (YEG) to Toronto (YYZ) 9.2/10 Wonderful! (330 reviews) Perfect for an overnight stay while moving in University student! Reviewed on Sep 17, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-10-20/2025-10-27/?FromAirport=YEG&Destination=YYZ&NumRoom=1&NumAdult=2&NumChild=0&hotelId=92703199&paandie=true&dealMarker=pb4i3zf3pAy3m0jjWmvebM-IYFa0z6xSnmkd8MxifDNAEJPJo-n4fWTjEXUO_-sP) ![GLOBALSTAY. Charming Yorkville Condos](https://images.trvl-media.com/lodging/39000000/38930000/38922600/38922596/620c0dcb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### GLOBALSTAY. Charming Yorkville Condos Old Toronto CA $961 per person Dec 7 - Dec 14 found 19 hours ago Roundtrip flight included Edmonton (YEG) to Toronto (YYZ) 7.8/10 Good! (131 reviews) Everything was great, except the tv did not work during our stay. Reviewed on Jun 19, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-07/2025-12-14/?FromAirport=YEG&Destination=YYZ&NumRoom=1&NumAdult=2&NumChild=0&hotelId=38922596&paandie=true&dealMarker=jIx63fnSgnLhpKxRCVLgz3e44s19X2uNcE3Pd8_W8N79AUaj4PWyo1DzF552_s1w) ![GLOBALSTAY. Gorgeous Apartments in the Heart of Toronto](https://images.trvl-media.com/lodging/23000000/22160000/22151400/22151301/1fe166a7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### GLOBALSTAY. Gorgeous Apartments in the Heart of Toronto Downtown Toronto CA $1,022 per person Nov 24 - Nov 30 found 1 day ago Roundtrip flight included Edmonton (YEG) to Toronto (YYZ) 8.2/10 Very Good! (845 reviews) The apartment was great, the view was awesome, it could have been more clean, one of the elevators were out of service so it made going in and out of the apartment very timely, the fire alarms went off at 5am 2 out of 4 nights there. The check in process was harder than it should have been. I never felt unsafe, and you hear normal city traffic from down below which is expected staying in a city. The apartment location was perfect for access to the city and lots of transportation options easily accessible, grocery store is located right across the street as well. Reviewed on Sep 17, 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=22151301&paandie=true&dealMarker=A_7a3Em_ifmnR2ylryw5Lpz07PEJliOQdAfvzp15bZYxcoADXhurcNUUnTACal2-) ## 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! (3,321 reviews) "Beautiful hotel and large room." Reviewed on Sep 16, 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/1000000/30000/28000/27994/24e98767_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 Sep 21 - Sep 22 includes taxes & fees 8.2/10 Very Good! (12,401 reviews) "Rooms would benefit from a refresh." Reviewed on Sep 16, 2025 [](https://expedia.ca/Hotel-Search?startDate=21%2F09%2F2025&endDate=22%2F09%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 Oct 13 - Oct 14 includes taxes & fees 8.4/10 Very Good! (4,603 reviews) "Our check in was very welcoming. The room is small but we soon got used to it. Beds are comfy enough. Pillows are comfortable. My only complaint would be the street noise but that’s not the hotel’s fault. It’s a great location for restaurants, subway access, shopping. We would definitely stay here ..." Reviewed on Sep 16, 2025 [](https://expedia.ca/Hotel-Search?startDate=13%2F10%2F2025&endDate=14%2F10%2F2025&selected=26247&PinnedHotelID=26247&HadPinnedHotel=true®ionId=9546) [See all 4,153 properties in Pickering](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=19%2F09%2F2025&endDate=20%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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[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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