Pickering Vacations from $758
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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, Herongate Barn Theatre and Annandale Golf and Country Club. Expedia has what you need to escape the everyday. Tailor your vacation to Pickering to match your travel style, whatever that may be!
The Latest Pickering vacation packages
Price found within the past 48 hours. Click for updated prices.
Courtland Heaven Retreats
$758
per person
Sep 21 - Sep 24
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Toronto (YYZ)
No reviews
Is a house rather than a hotel … had a beautiful garden … and the host was very welcoming and friendly and we had great conversations. A special place I will remember for a long time.
Reviewed on Aug 8, 2026
Hotel Riu Plaza Toronto
Downtown Toronto
$1,294
per person
Oct 5 - Oct 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
9.4/10 Exceptional! (4,484 reviews)
The staff we very polite and helpful. The rooms were nice and clean and the Hotel is close to lots of places to eat, stores and close to all tourist attractions. The free breakfast was amazing and has everything you can imagine.
Will definitely be my hotel that I will chose for my next visit to Toronto.
Reviewed on Aug 22, 2026
Shangri-La Toronto
Downtown Toronto
$1,180
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
9.6/10 Exceptional! (1,350 reviews)
Food poisoning!
Be careful with room service here.
Ordered room service as my only meal on check-in night. Woke up at 2:04 AM with stomach pain, and by 3:20 AM I threw up everything — violently sick for about two hours. No other food eaten, so the room service meal was the clear cause.
Reviewed on Aug 21, 2026
Residence Inn by Marriott Toronto Downtown / Entertainment District
Downtown Toronto
$1,560
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
9.2/10 Wonderful! (3,220 reviews)
Excellent hôtel bien situé dans le Entertainment district. Très propre avec toutes les commodité dans la chambre. Personnel charmant. Le stationnement est plutôt cher et il est mieux d’utiliser un site spécialisé. Considérant le prix le l’hôtel, le déjeuner, quoique bien et bien présenté, pourrait offrir plus de fruits frais et de viennoiseries. Nous avons beaucoup apprécié notre séjour et y retournerons sûrement.
Reviewed on Aug 21, 2026
Where to stay in Pickering
Find the best Pickering areas and neighborhoods for the activities you enjoy most. Learn more about Pickering
West Shore
If you're spending some time in West Shore, Lake Ontario and Petticoat Creek Conservation Area are top sights worth seeing.
Amberlea
While there might not be top attractions in Amberlea, you can explore the larger area and discover places like Toronto Zoo and Rouge National Urban Park.
Brock Ridge
If you're looking for some top things to see and do in Brock Ridge and surrounding area, you can visit Pickering Casino Resort and Rouge National Urban Park.
Duffin Heights
While Duffin Heights isn't home to many top sights, Pickering Casino Resort and Herongate Barn Theatre are some notable places to visit nearby.
Highbush
While Highbush might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Rouge National Urban Park and Toronto Zoo.
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 afterward.
Herongate Barn Theatre
8.4/10 (6 reviews)
This century-old dairy barn transforms into a stage for comedy and mystery while you dine. Savor comfort food in the original bull pen before ascending to the Hayloft Theatre for an evening of rustic charm.
Cineplex Cinemas Pickering
This upscale cinema offers premium movie experiences with VIP auditoriums featuring reclining seats and in-seat dining. Enjoy the adults-only lounge with craft cocktails before watching the latest blockbusters.
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.
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.
Luke Andrews Wood Sculptures
7.0/10 (2 reviews)
You can spend time browsing the exhibits at Luke Andrews Wood Sculptures during your travels in Pickering. You can attend a sporting event while in the area.
What to do in Pickering
Soccer Fans 2026: From Toronto 5-Day Eastern Canada Small-Group Tour
$1,451
per adult
From Toronto: Small Group 4-Day Eastern Canada Tour
$1,112
per adult
Pickering Hotel Deals
Pickering Casino Resort Hotel
888 Durham Live Ave Pickering ON
Fully refundableReserve now, pay when you stay
$99 nightly
$116 total
Sep 20 - Sep 21
Total with taxes and fees
Chelsea Hotel, Toronto
33 Gerrard St W Toronto ON
Fully refundableReserve now, pay when you stay
$166 nightly
$199 total
Sep 7 - Sep 8
Total with taxes and fees
Fairmont Royal York
100 Front St West Toronto ON
Fully refundableReserve now, pay when you stay
$234 nightly
$280 total
Sep 7 - Sep 8
Total with taxes and fees
9/10 Wonderful! (8,603 reviews)
"Spotless rooms, lovely staff"
Reviewed on Aug 22, 2026
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.
Find the Best Pickering Vacation Packages
Pickering Essential Information
Language | English |
|---|---|
Currency | Canadian dollars |
Closest Airport | Billy Bishop Toronto City Airport (YTZ) |
Population | 87,800 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | Canadian Automotive Museum, Herongate Barn Theatre and Parkwood Estate |
More vacations you might like
Frequently asked questions
How much does a Pickering vacation package cost?
Offering great value package deals from $758 on Expedia, you'll be thrilled with how little a vacation 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 generally find lower rates and better availability in January, February and October. Explore our cheap Pickering vacation packages and you could score some great off-season discounts.
How many days is enough for Pickering?
The ideal duration of your Pickering vacation depends on what you'd like to see. Generally, a few days to a week will give you plenty of time to visit all the top sights and discover 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 traveling on a weekday, when prices are often lower.
Is it cheaper to book a Pickering vacation as a package?
Expedia vacation 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 vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation 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 traveling on a whim.
How to plan a trip to Pickering?
- Pick your dates: What you'd like to do in Pickering and your favorite season can help you decide when to travel.
- Plan your budget wisely: In addition to the price of your accommodations, you'll need to consider other expenses too. These include transportation, food and flights. Also, put aside a little extra for unexpected costs that may crop up during your trip to Pickering.
- Explore Pickering with Expedia's trip planning tool: Gain insights into the top attractions and best hotels for your trip to Pickering. You can also save your favorite locations, collaborate with friends and family and organize your plans in one place.
- Decide your trip length: Think about how much time you'd like to spend discovering Pickering. Plan your itinerary so you can get to all the attractions and activities you're interested in at a comfortable pace.
- Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to choose a Pickering vacation package that brings all your bookings together.
- Book any activities or excursions: Here's the fun part — locking in everything you want to see and do. Browse some of the incredible things to do in Pickering and book your tickets in advance to save time (and maybe some money too!).
Does Expedia offer Book Now, Pay Later Pickering vacation packages?
Secure your perfect trip to Pickering with help from Expedia's Book Now, Pay Later vacations. No need to save like crazy or wait for your next payday — we've joined forces with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans mean you can spread the total cost across 3, 6 or 12 months. With no late payment fees or hidden charges, it's easy to stay on budget and snag great deals before they disappear.
Explore a world of travel with Expedia
- Visit Downtown Toronto
- Royal Conservatory of Music
- University of Toronto Scarborough
- Scarborough Village Vacations
- Path Underground Shopping Mall
- Hto Park
- Visit Toronto
- Ontario Place
- Chinatown Centre
- Markham Village
- Princess of Wales Theatre
- Rotary Park
- Spin Toronto
- Panasonic Theatre
- Whitby Vacations
- Ossington Avenue
- Graffiti Alley
- Ontario Legislative Building
- Riverdale Park
- Tiff Bell Lightbox
- Varsity Stadium
- Mztv Museum of Television
- Mount Pleasant Cemetery
- Ontario Vacations
- Meridian Hall
- Massey Hall
- Gardiner Museum
- Yonge-Dundas Square
- Kiever Synagogue
- Royal Bank Plaza
- Whitby History Museum & Children's Centre
- Royal Alexandra Theatre
- Toronto Zoo
- Cf Toronto Eaton Centre
- Scarborough Vacations
- Enercare Centre
- Toronto Dominion Gallery of Inuit Art
- The Annex Vacations
- Sunnybrook Hospital
- Hanlan's Point Beach
- Guild Inn Gardens
- Greek Town Vacations
- Second City
- Ajax Vacations
- Niagara Falls Vacations
- Cedarena
- Cbc Museum
- Trinity Bellwoods Park
- Toronto-Dominion Centre
- Scarborough Town Centre
- Metro Toronto Convention Centre
- Joyride 150 Indoor Bike Park
- Hudson's Bay Centre
- Canadian National Exhibition
- Church of the Holy Trinity
- Little India Vacations
- Harbourfront Vacations
- Little Italy Vacations
- Iskcon Scarborough
- Canon Theatre
- The Hospital for Sick Children
- Ryerson University
- Colonel Danforth Park
- St. Basil's Church
- Scotiabank Arena
- Casa Loma
- Toronto Vacations
- Canada's Wonderland
- Campbell House Museum
- Milne Dam Conservation Park
- Canada Permanent Building
- Tommy Thompson Park
- Centreville Amusement Park
- Markham Stouffville Hospital
- Yorkville Vacations
- Medieval Times
- Toronto Mendelssohn Choir
- Toronto Public Library
- St. Michael's Cathedral
- Rouge National Urban Park
- The Path
- Queen's Quay Terminal
- Kensington Market Vacations
- Cn Tower
- Lamport Stadium
- Chinatown Vacations
- Canada Sports Hall of Fame
- Elgin and Winter Garden Theatres
- Exhibition Place
- Sugar Beach
- Ontario College of Art & Design University
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
