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Pickering Vacation Packages

Choose two or more items and save on your trip:

Top Pickering Flight + Hotel Deals

The St. Regis Toronto

The St. Regis Toronto

5 out of 5
Financial District
Save 100% on your flightCA $1,051

CA $750

per person
Jan 12 - Jan 15
Roundtrip flight included
Montreal (YUL) to Toronto (YYZ)
4.7/5Exceptional! (996 reviews)

"Perfect location! The facility functions well having in mind the Covid-19 situation. Special thanks to Richard at the reception! Regards, V…"

Reviewed on Oct. 30, 2020

Sheraton Gateway Hotel In Toronto International Airport

Sheraton Gateway Hotel In Toronto International Airport

4 out of 5
CA $604

CA $440

per person
Jan 12 - Jan 15
Roundtrip flight included
Montreal (YUL) to Toronto (YYZ)
4.2/5Very Good! (2,014 reviews)

"Very convenient for airline passengers. Staff helpful.…"

Reviewed on Nov. 6, 2020

The Ivy at Verity

The Ivy at Verity

4.5 out of 5
Old Town
CA $881

CA $703

per person
Jan 12 - Jan 15
Roundtrip flight included
Montreal (YUL) to Toronto (YYZ)
4.7/5Exceptional! (211 reviews)

"What a beautiful place. Boutique hotel with only 4 rooms. Unique, romantic and full of caracter. I would go back every weekend. Amazing place for a getaway.…"

Reviewed on Oct. 12, 2020

The Westin Harbour Castle, Toronto

The Westin Harbour Castle, Toronto

4 out of 5
Central Waterfront
CA $443

CA $358

per person
Jan 12 - Jan 15
Roundtrip flight included
Montreal (YUL) to Toronto (YYZ)
4.4/5Excellent! (2,709 reviews)

"I liked the overall ambiance, liked how clean it was and friendly staff…"

Reviewed on Nov. 24, 2020

Sterling Inn & Spa - an Ontario's Finest Inn

Sterling Inn & Spa - an Ontario's Finest Inn

4 out of 5
CA $735

CA $599

per person
Dec 30 - Jan 2
Roundtrip flight included
Montreal (YUL) to Toronto (YYZ)
4.7/5Exceptional! (1,694 reviews)

"The Sterling Inn is a favourite of ours and for good reason. The rooms are large and spotless. The steam shower is decadent! Breakfast in bed, well no explanation needed there. We have stayed countless times and are never disappointed.…"

Reviewed on Nov. 7, 2020

2021 Pickering vacation deals

The St. Regis Toronto

The St. Regis Toronto

5 out of 5
Financial District
Save 100% on your flightCA $1,038

CA $736

per person
Mar 12 - Mar 15
Roundtrip flight included
Calgary (YYC) to Toronto (YYZ)
4.7/5Exceptional! (996 reviews)

"Perfect location! The facility functions well having in mind the Covid-19 situation. Special thanks to Richard at the reception! Regards, V…"

Reviewed on Oct. 30, 2020

Sheraton Gateway Hotel In Toronto International Airport

Sheraton Gateway Hotel In Toronto International Airport

4 out of 5
CA $604

CA $440

per person
Jan 12 - Jan 15
Roundtrip flight included
Montreal (YUL) to Toronto (YYZ)
4.2/5Very Good! (2,014 reviews)

"Very convenient for airline passengers. Staff helpful.…"

Reviewed on Nov. 6, 2020

The Ivy at Verity

The Ivy at Verity

4.5 out of 5
Old Town
CA $881

CA $703

per person
Jan 12 - Jan 15
Roundtrip flight included
Montreal (YUL) to Toronto (YYZ)
4.7/5Exceptional! (211 reviews)

"What a beautiful place. Boutique hotel with only 4 rooms. Unique, romantic and full of caracter. I would go back every weekend. Amazing place for a getaway.…"

Reviewed on Oct. 12, 2020

The Westin Harbour Castle, Toronto

The Westin Harbour Castle, Toronto

4 out of 5
Central Waterfront
CA $443

CA $358

per person
Jan 12 - Jan 15
Roundtrip flight included
Montreal (YUL) to Toronto (YYZ)
4.4/5Excellent! (2,709 reviews)

"I liked the overall ambiance, liked how clean it was and friendly staff…"

Reviewed on Nov. 24, 2020

Delta Hotels by Marriott Toronto Airport & Conference Centre

Delta Hotels by Marriott Toronto Airport & Conference Centre

3.5 out of 5
Etobicoke
CA $350

CA $290

per person
Mar 12 - Mar 15
Roundtrip flight included
Calgary (YYC) to Toronto (YYZ)
4.2/5Very Good! (1,116 reviews)

"Comfortable room and very friendly staff. Love that they accept dogs!…"

Reviewed on Oct. 4, 2020

Top Hotels in Pickering

Comfort Inn Pickering
Comfort Inn Pickering
2.5 out of 5
533 Kingston Rd., Pickering, ON
Free cancellationReserve now, pay when you stay
The price is CA $100 per night from Dec 4 to Dec 5
3.6/5Good! (900 reviews)

"Was good for a place to sleep in Pickering while on work project"…"

Reviewed on Nov. 21, 2020

Comfort Inn Pickering
Charming, Brand New Apartment in Pickering
Charming, Brand New Apartment in Pickering
1825 Appleview Rd, Pickering, ON
Get Rates
Charming, Brand New Apartment in Pickering
Fully Furnished Basement Apt With Extra Sofa Bed
Fully Furnished Basement Apt With Extra Sofa Bed
1541 Amberlea Rd, Pickering, ON
Get Rates
Fully Furnished Basement Apt With Extra Sofa Bed
See all 1988 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.

Top things to do in Pickering

Image for Medieval Times Dinner & Tournament Tickets in Toronto

Medieval Times Dinner & Tournament Tickets in Toronto

CA $75
Per adult
76% of travellers recommend
Medieval Times Dinner & Tournament Tickets in Toronto
Image for Canadian Automotive Museum Tickets

Canadian Automotive Museum Tickets

CA $14
Per adult
94% of travellers recommend
Canadian Automotive Museum Tickets
Image for CN Tower Observation Experience Toronto

CN Tower Observation Experience Toronto

CA $61
Per adult
CN Tower Observation Experience Toronto
See all activities in Pickering

What are the advantages of a road trip to Pickering?

Taking a Pickering road trip is the best way to travel while hitting all the stops along the way. There’s never been a better time to put all your road trip ideas to good use. Expedia offers incredible deals on hotels in Pickering, and you can save big when you opt for one of our packages in Pickering. Our packages combine your hotel and car rental into one low price, saving you more on both. 

How to plan a road trip to Pickering?

Planning a road trip is easy when you make all your itinerary bookings in one place—Expedia. You might take a camping road trip where all you need is a car and some gear. Car rentals are available in the pick-up and drop-off locations of your choosing. You might take a highway getaway to that city you’ve been dreaming of, bundling your hotel and car bookings for deep road trip discounts. 

What to do on a road trip to Pickering?

To make the most of any road trip adventure, you’ll want to have a road trip itinerary. That way, you won’t miss any of the road trip activities on your list. You can search for things to do in Pickering and other destinations before adding it to your plan.  

How to rent a car for a road trip?

Renting a car for a road trip is often the best way to travel. Don’t put miles or strain on your own vehicle and instead put your mind at ease when you opt for a safe car rental. Expedia offers wow-worthy deals on car rentals so you can choose the perfect car for your journey and preferences. Get the whole gang to pile in and hit the road for a great price. Vacation rentals in Pickering are waiting for you to arrive. Expedia will help you get there for less.

Frequently asked questions

How much does a Pickering vacation package cost?
Our Pickering vacation packages, which start from as low as CA $290, are the easiest way to save. Select your favorite flights, hotels and rental cars to create your dream trip.
If I'm not able to travel, can I cancel my Pickering vacation package?
Plans can change without warning, so yes. You may be able to cancel or alter your Pickering vacation package at no cost within 24 hours of booking. For older bookings, you can still make the necessary changes, but your car rental company, airline or hotel may impose a charge. Want more information? Visit our Customer Service Portal. We’ll help make sure your trip goes off without a hitch.
How do I get a cheap travel package to Pickering?
It’s as simple as bundling. Flights, rental cars and hotels — combine whatever you need into a Pickering vacation package and save up to C$590. Score even more bargains when you include extras such as tours or experiences to your booking. But here’s the impressive part. You have the flexibility to customize your vacation your way. We offer more than 400 partner airlines and 321,000 hotel options worldwide, so that everyone has an opportunity to travel and fulfill those vacation fantasies.
Where should I stay in Pickering?
A vacation in Pickering isn’t complete without paying a visit to Herongate Barn Theatre, Deer Creek North Golf Course and Glen Cedars Golf Club. Spend your evenings near these popular attractions and make sightseeing easy.
What are the top hotels in Pickering?
Whether you’ll be staying for one or several nights in Pickering, you’ll get a great night’s rest at Comfort Inn Pickering. This option is the first choice for plenty of travelers.
When is the best time of year to visit Pickering?
Pickering is busy in . If you’re not into big crowds and like a quieter pace, book your getaway for . Need to watch your vacation expenses? Pick up one of the bargains on offer in . is typically when prices increase and hotel rates are at their peak.
How far in advance should I book my Pickering vacation?
Reserving your flights early with Expedia means one less thing to worry about. Most air carriers advertise tickets up to a year in advance. This is often the cheapest time to book. If circumstances have left you booking late, last-minute deals to Pickering are still known to appear a few weeks before departure.
What does an Expedia Pickering travel package include?
Hotels, flights and a shiny set of wheels for all your fun road trip adventures. Simply choose your favorite 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 crafting your Pickering getaway, you’re in control!
What should I know before booking a Pickering travel package?
You can save big by bundling your airfares, hotels and rental cars. Once you’ve made your booking, add on fun stuff like sightseeing tours or experiences. Your next unforgettable adventure is only a few clicks away.
Does Expedia offer Book Now, Pay Later Pickering vacation packages?
Expedia has joined forces with online lender Affirm to help minimize any financial worry to do with your trip. This may be especially useful if your need to travel has cropped up suddenly. Book Now, Pay Later and spread the price of your flight and hotel package over a number of installments.
Can I choose my airline with a Pickering Expedia vacation package?
Yes, and with more than 550 airlines to pick from globally, you’ve got lots of choice. Take a look at the available options and find out which airline fits your needs and budget.

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