Title: Pickering Vacation Packages & Trips 2025/2026 from CA $414 | 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. ![The Waterside Inn](https://images.trvl-media.com/lodging/1000000/910000/904800/904736/502ca847_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Waterside Inn Port Credit CA $414 per person Jan 15 - Jan 18 found 1 day ago Roundtrip flight included Edmonton (YEG) to Toronto (YYZ) 8.4/10 Very Good! (1,011 reviews) We had a great stay. A great location with walking trails close by. It is a beautiful area right by the water. Reviewed on Nov 4, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-15/2026-01-18/?FromAirport=YEG&Destination=YYZ&NumRoom=1&NumAdult=2&NumChild=0&hotelId=904736&paandie=true&dealMarker=SobdS4fRoSNWigIz_WvKnuMRNKnk8hvbV3TAIawKPm1KyDxH4dtwvLWtN_TnvIVi) ![New 3BR Townhouse, Minutes to Niagara Falls and Brock University by GLOBALSTAY](https://images.trvl-media.com/lodging/93000000/92050000/92045400/92045305/2efed9ed_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### New 3BR Townhouse, Minutes to Niagara Falls and Brock University by GLOBALSTAY CA $1,404 per person Dec 26 - Jan 2 found 9 hours ago Roundtrip flight included Edmonton (YEG) to Toronto (YYZ) 8.6/10 Excellent! (22 reviews) Responsive host, clean house. The stay was good Reviewed on Oct 26, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2026-01-02/?FromAirport=YEG&Destination=YYZ&NumRoom=1&NumAdult=2&NumChild=0&hotelId=92045305&paandie=true&dealMarker=m71OEVPTDmQJpXJ1to-N9Xm2sR5Hia7KsYAC4Xzo5ZZctDaWxqiek-8kAVu87wg1) ![Hotel Riu Plaza Toronto](https://images.trvl-media.com/lodging/118000000/117280000/117279800/117279789/e2d68529_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Toronto Downtown Toronto CA $1,050 per person Dec 12 - Dec 18 found 1 day ago Roundtrip flight included Edmonton (YEG) to Toronto (YYZ) 9.2/10 Wonderful! (172 reviews) Great rooms and very nice breakfast Reviewed on Nov 9, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-12/2025-12-18/?FromAirport=YEG&Destination=YYZ&NumRoom=1&NumAdult=2&NumChild=0&hotelId=117279789&paandie=true&dealMarker=rhM3ZRW4btfEzjQCYBOoL2VdKjJC0VFzGYEzT4gAb_1wttJhknE2ezlZC-XdkY3h) ![Movich](https://images.trvl-media.com/lodging/96000000/95360000/95359500/95359442/dccfca58_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Movich Downtown Toronto CA $487 per person Feb 2 - Feb 5 found 1 day ago Roundtrip flight included Halifax (YHZ) to Toronto (YYZ) 7.6/10 Good! (24 reviews) Clean rooms, great location, very accommodating host Reviewed on Nov 4, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-02/2026-02-05/?FromAirport=YHZ&Destination=YYZ&NumRoom=1&NumAdult=2&NumChild=0&hotelId=95359442&paandie=true&dealMarker=SobdS4fRoSNWigIz_WvKnp-g4h_1KvaiQB2NIDgfCYLNPzhHb7cpCa20w-8PnY3A) ![Spacious 4-Bedroom Retreat](https://images.trvl-media.com/lodging/113000000/112550000/112543900/112543874/4a70fdfe_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Spacious 4-Bedroom Retreat CA $1,502 per person Dec 25 - Dec 28 found 24 hours ago Roundtrip flight included Vancouver (YVR) to Toronto (YYZ) No reviews [](https://expedia.ca/go/package/search/FlightHotel/2025-12-25/2025-12-28/?FromAirport=YVR&Destination=YYZ&NumRoom=1&NumAdult=2&NumChild=0&hotelId=112543874&paandie=true&dealMarker=zC80xzzhXU-zQ333H1tYOyXK0hSurGPNzUuJQlfjeufKdxn7ImqL6stN_UIVlgX3) ## 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 $129 CA $163 total Nov 25 - Nov 26 includes taxes & fees 8.8/10 Excellent! (3,613 reviews) 👍 Reviewed on Nov 9, 2025 [](https://expedia.ca/Hotel-Search?startDate=25%2F11%2F2025&endDate=26%2F11%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 $174 CA $214 total Nov 14 - Nov 15 includes taxes & fees 8.2/10 Very Good! (12,950 reviews) Clean room, good size TV, balcony, easy checkin and check out. Friendly staff. As described. Reviewed on Nov 7, 2025 [](https://expedia.ca/Hotel-Search?startDate=14%2F11%2F2025&endDate=15%2F11%2F2025&selected=27994&PinnedHotelID=27994&HadPinnedHotel=true®ionId=9546) ![Toronto Don Valley Hotel and Suites](https://images.trvl-media.com/lodging/1000000/10000/9000/8978/b0f8fd54_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Toronto Don Valley Hotel and Suites 175 Wynford Drive, Toronto, ON CA $134 CA $164 total Nov 11 - Nov 12 includes taxes & fees 7.4/10 Good! (6,122 reviews) Location, in hotel restaurant food was great and comfortable beds. Reviewed on Nov 7, 2025 [](https://expedia.ca/Hotel-Search?startDate=11%2F11%2F2025&endDate=12%2F11%2F2025&selected=8978&PinnedHotelID=8978&HadPinnedHotel=true®ionId=9546) [See all 4,293 properties in Pickering](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=11%2F11%2F2025&endDate=12%2F11%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 $176 per adult **94%** 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/50010619/9b1ee8e8-ad06-4122-826b-f592b6823a87.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) - [Whitby Vacations](https://www.expedia.ca/Whitby.d7606.Destination-Travel-Guides) ### Cars - [Avis Rental Cars in Ajax](https://www.expedia.ca/Avis-Car-Rentals-In-Ajax.d6047927-c41.Car-Rental-Guide-Suppliers) - [Budget Rental Cars in Ajax](https://www.expedia.ca/Budget-Car-Rentals-In-Ajax.d6047927-c39.Car-Rental-Guide-Suppliers) - [Car rental Ajax](https://www.expedia.ca/Car-Rentals-In-Ajax.d6047927.Car-Rental-Guide) - [Rental cars Pearson Intl. airport](https://www.expedia.ca/Car-Rentals-In-Pearson-Intl.d5921113.Car-Rental-Guide) - [Car rentals near Toronto](https://www.expedia.ca/Car-Rentals-In-Toronto.d178314.Car-Rental-Guide) - [Dollar Rent A Car Rental Cars in Ajax](https://www.expedia.ca/Dollar-Rent-A-Car-Car-Rentals-In-Ajax.d6047927-c43.Car-Rental-Guide-Suppliers) - [Enterprise Rental Cars in Ajax](https://www.expedia.ca/Enterprise-Car-Rentals-In-Ajax.d6047927-c15.Car-Rental-Guide-Suppliers) - [Hertz Rental Cars in Ajax](https://www.expedia.ca/Hertz-Car-Rentals-In-Ajax.d6047927-c40.Car-Rental-Guide-Suppliers) - 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