Port Perry Vacations from $761

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Your Port Perry Vacation

Come and discover this fascinating city for yourself with a Port Perry vacation package. Consider basing yourself in the neighborhood of Dagmar - Lakeridge, which is good for skiing and families, and your time here will be nothing short of unforgettable. In the mood for some sightseeing? A trip to Port Perry isn't complete without exploring Great Blue Heron Charity Casino, Ocala Winery and other big-ticket attractions. Expedia can help you escape the everyday. Tailor your vacation to Port Perry to match your travel style, whatever that may be.

The Latest Port Perry vacation packages

Price found within the past 48 hours. Click for updated prices.
Modern Lillian Street Condos Midtown Toronto

Modern Lillian Street Condos Midtown Toronto

4 out of 5
Old Toronto
Price was $1,074, price is now $761 per person
$761
per person
Sep 23 - Sep 28
found 13 hours ago
Roundtrip flight included
New York (NYC) to Toronto (YYZ)
8.4/10 Very Good! (301 reviews)
The confirmation process was complicated by the fact that several steps were required to finalize the contract. The room we got was not what I believed I requested but GlobalStay, the management firm would not provide any proof that I had mistakenly ordered the wrong room. Nor would they offer any option to correct the issue. The parking space that we were told to use was occupied by another vehicle. As requested by GlobalStay I provided photo evidence and a photo of where I ended up parking so GlobalStay could inform building management. They did not do so. Consequently my vehicle was ticketed for $150 dollars in fines. I would avoid GlobalStay if possible.

Reviewed on Jul 12, 2026

1 Hotel Toronto

1 Hotel Toronto

5 out of 5
Downtown Toronto
Price was $2,182, price is now $1,321 per person
$1,321
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
9.6/10 Exceptional! (762 reviews)

Hotel Riu Plaza Toronto

Hotel Riu Plaza Toronto

4 out of 5
Downtown Toronto
Price was $1,432, price is now $890 per person
$890
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
9.4/10 Exceptional! (3,874 reviews)
Siempre por lo menos un ascensor dañado . Muy buen desayuno . Trato amable

Reviewed on Jul 17, 2026

Four Seasons Hotel Toronto

Four Seasons Hotel Toronto

5 out of 5
Old Toronto
Price was $1,933, price is now $1,279 per person
$1,279
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
9.6/10 Exceptional! (978 reviews)
Great location, very friendly and helpful staff. Hotel is brand new and amenities are top notch.

Reviewed on Jul 17, 2026

Shangri-La Toronto

Shangri-La Toronto

5 out of 5
Downtown Toronto
Price was $2,041, price is now $1,425 per person
$1,425
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
9.6/10 Exceptional! (1,287 reviews)

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Stay near popular Port Perry attractions

Port Perry Waterfront

After visiting Port Perry Waterfront, make a plan to see the other sights and activities in Port Perry.
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Port Perry Hotel Deals

Willow Pond Bed and Breakfast

Willow Pond Bed and Breakfast

Port Perry ON
$156 nightly
The price is $176 total per night from Jul 19 to Jul 20
$176 total
Jul 19 - Jul 20
Total with taxes and fees
9.6/10 Exceptional! (20 reviews)
"Perfect spot to stay in Port Perry."

Reviewed on Jul 13, 2026

Willow Pond Bed and Breakfast
Modern luxury suite near historic downtown Port Perry

Modern luxury suite near historic downtown Port Perry

Port Perry ON
$179 nightly
The price is $203 total per night from Jul 19 to Jul 20
$203 total
Jul 19 - Jul 20
Total with taxes and fees
Modern luxury suite near historic downtown Port Perry
Pickering Casino Resort Hotel

Pickering Casino Resort Hotel

4 out of 5
888 Durham Live Ave Pickering ON
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $125 total per night from Jul 19 to Jul 20
$125 total
Jul 19 - Jul 20
Total with taxes and fees
9/10 Wonderful! (4,948 reviews)
"Great resort and friendly staff"

Reviewed on Jul 17, 2026

Pickering Casino Resort Hotel
See all 533 properties in Port Perry
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 Port Perry Vacation Packages

Port Perry Essential Information

Language
English
Currency
Canadian dollars
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Ocala Winery and Great Blue Heron Charity Casino

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Frequently asked questions

How much does a Port Perry vacation package cost?
You can snap up a vacation package to this destination from $761 on Expedia. But how much your vacation to Port Perry costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Port Perry?
December, January and February are the best times to look for cheap Port Perry vacation packages. Choosing to travel in less busy months means you can typically find lower prices on hotels and flights.
How many days is enough for Port Perry?
Generally, a handful of days is enough to visit the major sights during your Port Perry vacation. But if you'd like to have time to chill out or go on day trips, think about extending your itinerary.
How to find the best Port Perry package deals?
Begin your search for a Port Perry package deal by entering your destination and preferred trip dates under our "Packages" tab. Then add a few filters, like "Property type" and "Guest rating," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Port Perry package deal right away, simply switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Port Perry adventure off to a flying start.
Is it cheaper to book a Port Perry vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and stays individually. Better still, you can customize your Port Perry escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Port Perry?
If you've got your Port Perry vacation dates finalized, book as soon as you can to grab some fantastic deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are ideal for quick escapes.
Does Expedia offer Book Now, Pay Later Port Perry vacation packages?
Set off on your dream trip to Port Perry with help from our 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 give you more flexibility and choice. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no hidden charges or late payment fees, you can easily budget for your trip and snap up bargains before they sell out.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.