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Grey Highlands

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Grey Highlands Flights as Low as $189

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

Flair Airlines
Thu, Jun 25 - Mon, Jul 13
YYC
Calgary Intl.
YKF
Region of Waterloo Intl.
$189 Roundtrip, just found
$189
Roundtrip
just found
Select Flair Airlines flight, departing Thu, Jun 25 from Calgary Intl. to Region of Waterloo Intl., returning Mon, Jul 13, priced at $189 just found
Flair Airlines
Wed, Sep 2 - Mon, Sep 7
YWG
Winnipeg James Armstrong Richardson Intl.
YYZ
Pearson Intl.
$204 Roundtrip, found 5 days ago
$204
Roundtrip
found 5 days ago
Select Flair Airlines flight, departing Wed, Sep 2 from Winnipeg James Armstrong Richardson Intl. to Pearson Intl., returning Mon, Sep 7, priced at $204 found 5 days ago
Flair Airlines
Sat, Sep 19 - Sat, Sep 26
FLL
Fort Lauderdale - Hollywood Intl.
YYZ
Pearson Intl.
$209 Roundtrip, found 2 hours ago
$209
Roundtrip
found 2 hours ago
Select Flair Airlines flight, departing Sat, Sep 19 from Fort Lauderdale - Hollywood Intl. to Pearson Intl., returning Sat, Sep 26, priced at $209 found 2 hours ago
Flair Airlines
Thu, Oct 15 - Tue, Oct 20
YYC
Calgary Intl.
YYZ
Pearson Intl.
$218 Roundtrip, found 1 day ago
$218
Roundtrip
found 1 day ago
Select Flair Airlines flight, departing Thu, Oct 15 from Calgary Intl. to Pearson Intl., returning Tue, Oct 20, priced at $218 found 1 day ago
WestJet
Fri, Sep 4 - Wed, Sep 9
YWG
Winnipeg James Armstrong Richardson Intl.
YYZ
Pearson Intl.
$232 Roundtrip, found 5 days ago
$232
Roundtrip
found 5 days ago
Select WestJet flight, departing Fri, Sep 4 from Winnipeg James Armstrong Richardson Intl. to Pearson Intl., returning Wed, Sep 9, priced at $232 found 5 days ago
Porter Airlines
Sun, Aug 30 - Wed, Sep 9
YWG
Winnipeg James Armstrong Richardson Intl.
YYZ
Pearson Intl.
$232 Roundtrip, found 5 days ago
$232
Roundtrip
found 5 days ago
Select Porter Airlines flight, departing Sun, Aug 30 from Winnipeg James Armstrong Richardson Intl. to Pearson Intl., returning Wed, Sep 9, priced at $232 found 5 days ago
Air Canada
Sat, Jul 11 - Sat, Jul 18
FLL
Fort Lauderdale - Hollywood Intl.
YHM
John C. Munro Hamilton Intl.
$252 Roundtrip, found 16 hours ago
$252
Roundtrip
found 16 hours ago
Select Air Canada flight, departing Sat, Jul 11 from Fort Lauderdale - Hollywood Intl. to John C. Munro Hamilton Intl., returning Sat, Jul 18, priced at $252 found 16 hours ago
Porter Airlines
Thu, Aug 20 - Thu, Aug 20
YYT
St. John's Intl.
YYZ
Pearson Intl.
$272 Roundtrip, found 6 days ago
$272
Roundtrip
found 6 days ago
Select Porter Airlines flight, departing Thu, Aug 20 from St. John's Intl. to Pearson Intl., returning Thu, Aug 20, priced at $272 found 6 days ago
Porter Airlines
Thu, Aug 27 - Tue, Sep 1
YYT
St. John's Intl.
YHM
John C. Munro Hamilton Intl.
$287 Roundtrip, found 5 days ago
$287
Roundtrip
found 5 days ago
Select Porter Airlines flight, departing Thu, Aug 27 from St. John's Intl. to John C. Munro Hamilton Intl., returning Tue, Sep 1, priced at $287 found 5 days ago
Porter Airlines
Sun, Jun 21 - Thu, Jun 25
YWG
Winnipeg James Armstrong Richardson Intl.
YHM
John C. Munro Hamilton Intl.
$355 Roundtrip, found 5 days ago
$355
Roundtrip
found 5 days ago
Select Porter Airlines flight, departing Sun, Jun 21 from Winnipeg James Armstrong Richardson Intl. to John C. Munro Hamilton Intl., returning Thu, Jun 25, priced at $355 found 5 days ago
Air Canada
Fri, Aug 14 - Sun, Aug 16
FLL
Fort Lauderdale - Hollywood Intl.
YKF
Region of Waterloo Intl.
$361 Roundtrip, found 23 hours ago
$361
Roundtrip
found 23 hours ago
Select Air Canada flight, departing Fri, Aug 14 from Fort Lauderdale - Hollywood Intl. to Region of Waterloo Intl., returning Sun, Aug 16, priced at $361 found 23 hours ago
Air Canada
Tue, Jun 16 - Wed, Jun 17
FLL
Fort Lauderdale - Hollywood Intl.
YTZ
Billy Bishop Toronto City
$383 Roundtrip, found 2 hours ago
$383
Roundtrip
found 2 hours ago
Select Air Canada flight, departing Tue, Jun 16 from Fort Lauderdale - Hollywood Intl. to Billy Bishop Toronto City, returning Wed, Jun 17, priced at $383 found 2 hours ago
Porter Airlines
Fri, Jun 19 - Mon, Jun 22
YWG
Winnipeg James Armstrong Richardson Intl.
YTZ
Billy Bishop Toronto City
$397 Roundtrip, found 6 days ago
$397
Roundtrip
found 6 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 $397 found 6 days ago
Porter Airlines
Mon, Jun 22 - Mon, Jun 29
YYT
St. John's Intl.
YTZ
Billy Bishop Toronto City
$532 Roundtrip, found 17 hours ago
$532
Roundtrip
found 17 hours ago
Select Porter Airlines flight, departing Mon, Jun 22 from St. John's Intl. to Billy Bishop Toronto City, returning Mon, Jun 29, priced at $532 found 17 hours ago
Air Canada
Thu, Jun 18 - Mon, Jun 22
YYT
St. John's Intl.
YKF
Region of Waterloo Intl.
$688 Roundtrip, found 19 hours ago
$688
Roundtrip
found 19 hours ago
Select Air Canada flight, departing Thu, Jun 18 from St. John's Intl. to Region of Waterloo Intl., returning Mon, Jun 22, priced at $688 found 19 hours ago
Air Canada
Fri, Jun 19 - Mon, Jun 22
YWG
Winnipeg James Armstrong Richardson Intl.
YKF
Region of Waterloo Intl.
$742 Roundtrip, found 3 hours ago
$742
Roundtrip
found 3 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 $742 found 3 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 $189, 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 $189 right now, why wait?

Grey Highlands Flight Information
Destination airport
Pearson Intl.
Destination airport IATA code
YYZ
Roundtrip price
$208

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! (434 reviews)
"Clean, perfect for stopover"

Reviewed on Jun 12, 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! (5,331 reviews)
"The pool at weirder lodge where we stayed was in maintenance which was disappointing But the room was great"

Reviewed on Jun 14, 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! (1,577 reviews)
"Spa is amazing."

Reviewed on Jun 8, 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! (1,667 reviews)
"Was clean but a little dated and worn out furniture and couches in common areas."

Reviewed on Jun 14, 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! (1,387 reviews)
"Beautiful hotel in a lovely village. Everything was so handy. Parked the car and never had to move it. Lots of restaurants within walking distance."

Reviewed on Jun 14, 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! (1,422 reviews)
"We stayed at the Mosaic and had a wonderful experience. The staff at the hotel and throughout the resort restaurants were friendly, welcoming, and helpful. The food across the resort was amazing! I highly recommend the Greek restaurant, the Italian restaurant, and Firehall Pizza Company. Every meal ..."

Reviewed on Jun 14, 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! (1,258 reviews)
"We stayed two nights. No house keeping, no coffee refilled . But I could get one bag at the reception."

Reviewed on Jun 12, 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! (1,008 reviews)
"3.5 stars…Our stay was okay, the room is decent but it could be cleaner. Some areas were so dusty, like beside the microwave and other surface areas. I wish there was an area to get coffee by the lounge but nothing much happening in the lobby. The view was beautiful though."

Reviewed on Jun 14, 2026

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Best Western Inn On The Bay
See all 1,561 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.