Port Perry Vacations from $462

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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.
Crowne Plaza Toronto Airport by IHG

Crowne Plaza Toronto Airport by IHG

4 out of 5
Etobicoke
Price was $692, price is now $462 per person
$462
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Toronto (YYZ)
8.2/10 Very Good! (3,350 reviews)
Easy check in Snack bar was ok Airport shuttle was great Rooms were clean but I was super itchy the next day maybe from the sheets or shower soap I was room 547 and it was pretty noisy in the hallway so wasn’t the best sleep Lots of thumping and doors slamming I guess as people leave their rooms for their flights

Reviewed on Jun 17, 2026

Hotel Riu Plaza Toronto

Hotel Riu Plaza Toronto

4 out of 5
Downtown Toronto
Price was $1,273, price is now $776 per person
$776
per person
Jul 27 - Jul 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
9.2/10 Wonderful! (3,600 reviews)
The hotel was beautiful, clean and staff was very friendly. Rooms were not ready at check in time but not too much later. Hotel bar is busy and had only one bartender working but he did an amazing job. Downtown location is great. Overall, a great experience and would stay again.

Reviewed on Jun 17, 2026

One King West Hotel & Residence

One King West Hotel & Residence

4 out of 5
Downtown Toronto
Price was $837, price is now $545 per person
$545
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Toronto (YYZ)
9.4/10 Exceptional! (7,957 reviews)
Having fifa 26 around the lobby was a nice touch

Reviewed on Jun 17, 2026

The Waterside Inn

The Waterside Inn

3.5 out of 5
Port Credit
Price was $822, price is now $559 per person
$559
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
8.6/10 Excellent! (1,018 reviews)
The room was spacious and the location of the hotel was perfect. Close to the water and shops and restaurants and the train to Toronto.

Reviewed on Jun 16, 2026

GLOBALSTAY Luxury 4 Bedroom House

GLOBALSTAY Luxury 4 Bedroom House

4 out of 5
Woodbridge
Save 100% on your flight
Price was $1,707, price is now $1,167 per person
$1,167
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
10/10 Exceptional! (6 reviews)
We had a wonderful stay at this house. The neighbourhood was very peaceful and quiet, but still close to everything, which made it perfect for relaxing. The home itself was very spacious, clean, and comfortable, with plenty of room for everyone to feel at home. The staff was also very responsive and helpful throughout our stay, answering questions quickly and making the whole experience smooth and stress free. Overall, a great place to stay and we would definitely come back again.

Reviewed on May 11, 2026

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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
$149 nightly
The price is $168 total per night from Jun 21 to Jun 22
$168 total
Jun 21 - Jun 22
Total with taxes and fees
9.8/10 Exceptional! (17 reviews)
"Very comfortable rooms. Based on our schedule we could only do the continental breakfast, it was delicious and lots of selection. Lynn the host was very responsive when messaging."

Reviewed on May 31, 2026

Willow Pond Bed and Breakfast
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
$99 nightly
The price is $117 total per night from Jul 6 to Jul 7
$117 total
Jul 6 - Jul 7
Total with taxes and fees
9/10 Wonderful! (4,838 reviews)
"accès à l'autoroute 401, 30 minutes de Toronto3"

Reviewed on Jun 17, 2026

Pickering Casino Resort Hotel
Travelodge by Wyndham Oshawa Whitby

Travelodge by Wyndham Oshawa Whitby

2 out of 5
940 Champlain Avenue Oshawa ON
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $92 total per night from Jul 19 to Jul 20
$92 total
Jul 19 - Jul 20
Total with taxes and fees
6.8/10 (1,054 reviews)
"This property use to be nice, but it's gone down hill. I booked it because I wanted to use the pool and hot tub. Got there and the pool was drained and the hot tub was walled off. I decided to have a hot bath because, no hot tub, there wasn't a plug for the tub. I called the front desk and was told ..."

Reviewed on Jun 17, 2026

Travelodge by Wyndham Oshawa Whitby
See all 531 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 $462 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.