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Grey Highlands

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Grey Highlands Flights as Low as $166

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Flair Airlines
Fri, Jun 19 - Mon, Jun 22
YWG
Winnipeg James Armstrong Richardson Intl.
YYZ
Pearson Intl.
$166 Roundtrip, found 1 day ago
$166
Roundtrip
found 1 day ago
Select Flair Airlines flight, departing Fri, Jun 19 from Winnipeg James Armstrong Richardson Intl. to Pearson Intl., returning Mon, Jun 22, priced at $166 found 1 day ago
Porter Airlines
Sun, Jun 21 - Mon, Jun 22
YWG
Winnipeg James Armstrong Richardson Intl.
YHM
John C. Munro Hamilton Intl.
$210 Roundtrip, found 1 day ago
$210
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Sun, Jun 21 from Winnipeg James Armstrong Richardson Intl. to John C. Munro Hamilton Intl., returning Mon, Jun 22, priced at $210 found 1 day ago
Flair Airlines
Sat, Aug 8 - Tue, Aug 11
FLL
Fort Lauderdale - Hollywood Intl.
YYZ
Pearson Intl.
$210 Roundtrip, found 3 days ago
$210
Roundtrip
found 3 days ago
Select Flair Airlines flight, departing Sat, Aug 8 from Fort Lauderdale - Hollywood Intl. to Pearson Intl., returning Tue, Aug 11, priced at $210 found 3 days ago
Porter Airlines
Sat, Jul 18 - Mon, Jul 20
FLL
Fort Lauderdale - Hollywood Intl.
YHM
John C. Munro Hamilton Intl.
$230 Roundtrip, found 3 days ago
$230
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Sat, Jul 18 from Fort Lauderdale - Hollywood Intl. to John C. Munro Hamilton Intl., returning Mon, Jul 20, priced at $230 found 3 days ago
Porter Airlines
Sun, Jul 5 - Sun, Jul 12
BOS
Logan Intl.
YTZ
Billy Bishop Toronto City
$242 Roundtrip, found 17 hours ago
$242
Roundtrip
found 17 hours ago
Select Porter Airlines flight, departing Sun, Jul 5 from Logan Intl. to Billy Bishop Toronto City, returning Sun, Jul 12, priced at $242 found 17 hours ago
Air Transat
Wed, Jun 17 - Mon, Jun 22
YWG
Winnipeg James Armstrong Richardson Intl.
YHM
John C. Munro Hamilton Intl.
$244 Roundtrip, found 9 hours ago
$244
Roundtrip
found 9 hours ago
Select Air Transat flight, departing Wed, Jun 17 from Winnipeg James Armstrong Richardson Intl. to John C. Munro Hamilton Intl., returning Mon, Jun 22, priced at $244 found 9 hours ago
Porter Airlines
Sat, Jul 4 - Fri, Jul 10
BOS
Logan Intl.
YYZ
Pearson Intl.
$251 Roundtrip, found 1 day ago
$251
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Sat, Jul 4 from Logan Intl. to Pearson Intl., returning Fri, Jul 10, priced at $251 found 1 day ago
Air Canada
Sat, Aug 1 - Sat, Aug 1
BOS
Logan Intl.
YYZ
Pearson Intl.
$260 Roundtrip, found 2 days ago
$260
Roundtrip
found 2 days ago
Select Air Canada flight, departing Sat, Aug 1 from Logan Intl. to Pearson Intl., returning Sat, Aug 1, priced at $260 found 2 days ago
American Airlines
Sat, Aug 8 - Tue, Aug 11
FLL
Fort Lauderdale - Hollywood Intl.
YYZ
Pearson Intl.
$286 Roundtrip, found 3 days ago
$286
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Aug 8 from Fort Lauderdale - Hollywood Intl. to Pearson Intl., returning Tue, Aug 11, priced at $286 found 3 days ago
Air Canada
Fri, Jun 19 - Mon, Jun 22
YWG
Winnipeg James Armstrong Richardson Intl.
YKF
Region of Waterloo Intl.
$349 Roundtrip, found 12 hours ago
$349
Roundtrip
found 12 hours ago
Select Air Canada flight, departing Fri, Jun 19 from Winnipeg James Armstrong Richardson Intl. to Region of Waterloo Intl., returning Mon, Jun 22, priced at $349 found 12 hours ago
Porter Airlines
Fri, Jun 19 - Mon, Jun 22
YWG
Winnipeg James Armstrong Richardson Intl.
YTZ
Billy Bishop Toronto City
$349 Roundtrip, found 2 days ago
$349
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Fri, Jun 19 from Winnipeg James Armstrong Richardson Intl. to Billy Bishop Toronto City, returning Mon, Jun 22, priced at $349 found 2 days ago
Air Canada
Thu, Jun 11 - Mon, Jun 15
FLL
Fort Lauderdale - Hollywood Intl.
YKF
Region of Waterloo Intl.
$413 Roundtrip, found 1 day ago
$413
Roundtrip
found 1 day ago
Select Air Canada flight, departing Thu, Jun 11 from Fort Lauderdale - Hollywood Intl. to Region of Waterloo Intl., returning Mon, Jun 15, priced at $413 found 1 day ago
WestJet
Thu, Aug 13 - Tue, Sep 1
SFO
San Francisco Intl.
YYZ
Pearson Intl.
$441 Roundtrip, found 3 days ago
$441
Roundtrip
found 3 days ago
Select WestJet flight, departing Thu, Aug 13 from San Francisco Intl. to Pearson Intl., returning Tue, Sep 1, priced at $441 found 3 days ago
United
Mon, Jun 8 - Tue, Jun 16
FLL
Fort Lauderdale - Hollywood Intl.
YTZ
Billy Bishop Toronto City
$451 Roundtrip, found 3 days ago
$451
Roundtrip
found 3 days ago
Select United flight, departing Mon, Jun 8 from Fort Lauderdale - Hollywood Intl. to Billy Bishop Toronto City, returning Tue, Jun 16, priced at $451 found 3 days ago
Air Canada
Fri, Jul 31 - Sun, Aug 2
BOS
Logan Intl.
YKF
Region of Waterloo Intl.
$469 Roundtrip, found 1 day ago
$469
Roundtrip
found 1 day ago
Select Air Canada flight, departing Fri, Jul 31 from Logan Intl. to Region of Waterloo Intl., returning Sun, Aug 2, priced at $469 found 1 day ago
Air Canada
Wed, Jul 15 - Wed, Jul 22
SFO
San Francisco Intl.
YKF
Region of Waterloo Intl.
$568 Roundtrip, found 10 hours ago
$568
Roundtrip
found 10 hours ago
Select Air Canada flight, departing Wed, Jul 15 from San Francisco Intl. to Region of Waterloo Intl., returning Wed, Jul 22, priced at $568 found 10 hours ago

Cheap Flights to Grey Highlands

Fall in love at first flight with your vacation to Grey Highlands by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Grey Highlands on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Grey Highlands, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Grey Highlands

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Grey Highlands with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the YOS airport.

What is the cheapest month to fly to Grey Highlands?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Grey Highlands are in June, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Grey Highlands?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Grey Highlands.

What airport is best to fly into Grey Highlands?

When you’re planning your trip to Grey Highlands, convenience is the name of the game. Luckily, Grey Highlands Region of Waterloo Intl. Airport is nearby so you can deplane and get going on checking off everything on your Grey Highlands must-do list.

How much are flights to Grey Highlands?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Grey Highlands on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $166, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Grey Highlands?

The trick to saving a stack of cash on your flight to Grey Highlands? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $166 right now, why wait?

Grey Highlands Flight Information
Destination airport
Pearson Intl.
Destination airport IATA code
YYZ
Roundtrip price
$210

Last Minute Hotel Deals in Grey Highlands

Leelas Villa Inn Flesherton

Leelas Villa Inn Flesherton

3 out of 5
774107 Highway 10 South Grey Highlands ON
Stay at this hotel in Grey Highlands. Enjoy free WiFi, room service, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
8.6/10 Excellent! (433 reviews)
"I don’t mean to be too harsh or rude but while I was there the only thing I could confidently say is that it was extremely close to a breakfast spot. When I checked in I was happy with the staff and the owner/manager. He was very nice and friendly but when I went into my room it appeared clean. There ..."

Reviewed on Jun 2, 2026

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Leelas Villa Inn Flesherton
Blue Mountain Resort Village Suites

Blue Mountain Resort Village Suites

4 out of 5
156 Jozo Weider Blvd The Blue Mountains ON
Book a stay at this ski hotel in The Blue Mountains. Enjoy free WiFi, an outdoor pool, and 10 restaurants. Our guests praise the pool and the helpful staff in ...
8.8/10 Excellent! (5,323 reviews)
"Great location, right in Blue Mountain Village. Room was clean and comfortable. We were on the ground floor facing ticket booth and outside noise was not a bother. Only one thing that was not great was no hot water for shower in the morning."

Reviewed on Jun 7, 2026

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Blue Mountain Resort Village Suites
Living Water Resort and Spa

Living Water Resort and Spa

3.5 out of 5
9 Harbour Street East Collingwood ON
Book a stay at this spa resort in Collingwood. Enjoy an outdoor pool, a full-service spa, and a marina. Our guests praise the restaurant and the helpful staff ...
8.4/10 Very Good! (1,568 reviews)
"Outdoor hot tub and spa was good but it recommended to book the spa before you visit"

Reviewed on Jun 6, 2026

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Living Water Resort and Spa
Blue Mountain Resort Inn

Blue Mountain Resort Inn

2.5 out of 5
110 Jozo Weider Blvd The Blue Mountains ON
Book a stay at this golf hotel in The Blue Mountains. Enjoy free WiFi, free parking, and a golf course. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (1,657 reviews)
"Staff was great and helpful, food at the restaurants was delicious. Rooms are dated and need some TLC but beds are comfy!"

Reviewed on Jun 7, 2026

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Blue Mountain Resort Inn
Westin Trillium House, Blue Mountain

Westin Trillium House, Blue Mountain

4 out of 5
220 Gord Canning Drive The Blue Mountains ON
Book a stay at this beach hotel in The Blue Mountains. Enjoy a golf course, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
9.2/10 Wonderful! (1,378 reviews)
"Wonderful experience; already booked our next stay!"

Reviewed on Jun 2, 2026

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Westin Trillium House, Blue Mountain
Blue Mountain Resort Mosaic Suites

Blue Mountain Resort Mosaic Suites

2.5 out of 5
190 Jozo Weider Blvd The Blue Mountains ON
Book a stay at this spa hotel in The Blue Mountains. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the helpful staff ...
8.8/10 Excellent! (1,421 reviews)
"The rooms are comfortable and well appointed, well -considered for our families. During the time of our stay, it was being renovated, so the rooms were much improved. Was well planned for construction, nonetheless came with some dust and detours. Surely it will be beautiful this summer. The gym is ..."

Reviewed on Jun 7, 2026

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Blue Mountain Resort Mosaic Suites
Living Stone Golf Resort

Living Stone Golf Resort

3 out of 5
19 Keith Ave Collingwood ON
Book a stay at this golf resort in Collingwood. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in ...
8.2/10 Very Good! (1,256 reviews)
"It was better than the last time I was there"

Reviewed on Jun 3, 2026

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Living Stone Golf Resort
Best Western Inn On The Bay

Best Western Inn On The Bay

2.5 out of 5
1800 2nd Avenue East Owen Sound ON
Stay at this hotel in Owen Sound. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.8/10 Excellent! (1,006 reviews)
"Nice location , room is clean ,staff friendly"

Reviewed on Jun 5, 2026

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Best Western Inn On The Bay
See all 1,562 properties in Grey Highlands
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.