Search Cheap Flights to
Winchester

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Winchester Flights as Low as $211

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

WestJet
Mon, Jul 21 - Sat, Jul 26
YVR
Vancouver Intl.
YOW
Macdonald-Cartier Intl.
$211 Roundtrip, found 11 hours ago
$211
Roundtrip
found 11 hours ago
Select WestJet flight, departing Mon, Jul 21 from Vancouver Intl. to Macdonald-Cartier Intl., returning Sat, Jul 26, priced at $211 found 11 hours ago
Porter Airlines
Thu, Jul 24 - Tue, Jul 29
YVR
Vancouver Intl.
YOW
Macdonald-Cartier Intl.
$231 Roundtrip, found 10 hours ago
$231
Roundtrip
found 10 hours ago
Select Porter Airlines flight, departing Thu, Jul 24 from Vancouver Intl. to Macdonald-Cartier Intl., returning Tue, Jul 29, priced at $231 found 10 hours ago
Porter Airlines
Thu, Jul 24 - Tue, Jul 29
YVR
Vancouver Intl.
YOW
Macdonald-Cartier Intl.
$234 Roundtrip, found 10 hours ago
$234
Roundtrip
found 10 hours ago
Select Porter Airlines flight, departing Thu, Jul 24 from Vancouver Intl. to Macdonald-Cartier Intl., returning Tue, Jul 29, priced at $234 found 10 hours ago
Porter Airlines
Tue, Jul 22 - Thu, Jul 31
YVR
Vancouver Intl.
YOW
Macdonald-Cartier Intl.
$247 Roundtrip, found 11 hours ago
$247
Roundtrip
found 11 hours ago
Select Porter Airlines flight, departing Tue, Jul 22 from Vancouver Intl. to Macdonald-Cartier Intl., returning Thu, Jul 31, priced at $247 found 11 hours ago
Air Canada
Thu, May 29 - Thu, Jun 5
FLL
Fort Lauderdale - Hollywood Intl.
YOW
Macdonald-Cartier Intl.
$267 Roundtrip, found 15 hours ago
$267
Roundtrip
found 15 hours ago
Select Air Canada flight, departing Thu, May 29 from Fort Lauderdale - Hollywood Intl. to Macdonald-Cartier Intl., returning Thu, Jun 5, priced at $267 found 15 hours ago
Bargain Flight
Tue, May 27 - Tue, May 27
EWR
Newark Liberty Intl. Airport
YOW
Macdonald-Cartier Intl.
$272 Roundtrip, found 23 hours ago
$272
Roundtrip
found 23 hours ago
Select Bargain Flight flight, departing Tue, May 27 from Newark Liberty Intl. Airport to Macdonald-Cartier Intl., returning Tue, May 27, priced at $272 found 23 hours ago
United
Sat, May 31 - Thu, Jun 5
FLL
Fort Lauderdale - Hollywood Intl.
YOW
Macdonald-Cartier Intl.
$303 Roundtrip, found 1 day ago
$303
Roundtrip
found 1 day ago
Select United flight, departing Sat, May 31 from Fort Lauderdale - Hollywood Intl. to Macdonald-Cartier Intl., returning Thu, Jun 5, priced at $303 found 1 day ago
Air Transat
Fri, Jul 25 - Tue, Jul 29
YVR
Vancouver Intl.
YOW
Macdonald-Cartier Intl.
$386 Roundtrip, found 10 hours ago
$386
Roundtrip
found 10 hours ago
Select Air Transat flight, departing Fri, Jul 25 from Vancouver Intl. to Macdonald-Cartier Intl., returning Tue, Jul 29, priced at $386 found 10 hours ago
WestJet
Mon, Jun 23 - Wed, Jun 25
YXX
Abbotsford Intl.
YOW
Macdonald-Cartier Intl.
$536 Roundtrip, found 19 hours ago
$536
Roundtrip
found 19 hours ago
Select WestJet flight, departing Mon, Jun 23 from Abbotsford Intl. to Macdonald-Cartier Intl., returning Wed, Jun 25, priced at $536 found 19 hours ago
Air Canada
Wed, Jun 4 - Wed, Jul 2
IST
Istanbul
YOW
Macdonald-Cartier Intl.
$684 Roundtrip, found 1 day ago
$684
Roundtrip
found 1 day ago
Select Air Canada flight, departing Wed, Jun 4 from Istanbul to Macdonald-Cartier Intl., returning Wed, Jul 2, priced at $684 found 1 day ago
LOT-Polish Airlines
Mon, Jun 2 - Mon, Jun 30
IST
Istanbul
YOW
Macdonald-Cartier Intl.
$994 Roundtrip, found 22 hours ago
$994
Roundtrip
found 22 hours ago
Select LOT-Polish Airlines flight, departing Mon, Jun 2 from Istanbul to Macdonald-Cartier Intl., returning Mon, Jun 30, priced at $994 found 22 hours ago
Air France
Wed, Jun 4 - Wed, Jul 2
IST
Istanbul
XDS
Ottawa Train Station
$1,110 Roundtrip, found 6 days ago
$1,110
Roundtrip
found 6 days ago
Select Air France flight, departing Wed, Jun 4 from Istanbul to Ottawa Train Station, returning Wed, Jul 2, priced at $1,110 found 6 days ago
Lufthansa
Fri, May 30 - Wed, Jul 2
IST
Istanbul
YOW
Macdonald-Cartier Intl.
$1,313 Roundtrip, found 3 days ago
$1,313
Roundtrip
found 3 days ago
Select Lufthansa flight, departing Fri, May 30 from Istanbul to Macdonald-Cartier Intl., returning Wed, Jul 2, priced at $1,313 found 3 days ago
Pegasus Airlines
Wed, Jun 4 - Wed, Jul 2
SAW
Sabiha Gokcen Intl.
XDS
Ottawa Train Station
$1,388 Roundtrip, found 3 days ago
$1,388
Roundtrip
found 3 days ago
Select Pegasus Airlines flight, departing Wed, Jun 4 from Sabiha Gokcen Intl. to Ottawa Train Station, returning Wed, Jul 2, priced at $1,388 found 3 days ago
Air France
Sun, Jun 1 - Thu, Jul 3
IST
Istanbul
YOW
Macdonald-Cartier Intl.
$1,565 Roundtrip, found 1 day ago
$1,565
Roundtrip
found 1 day ago
Select Air France flight, departing Sun, Jun 1 from Istanbul to Macdonald-Cartier Intl., returning Thu, Jul 3, priced at $1,565 found 1 day ago
KLM
Mon, Jun 2 - Mon, Jun 30
SAW
Sabiha Gokcen Intl.
XDS
Ottawa Train Station
$1,755 Roundtrip, found 22 hours ago
$1,755
Roundtrip
found 22 hours ago
Select KLM flight, departing Mon, Jun 2 from Sabiha Gokcen Intl. to Ottawa Train Station, returning Mon, Jun 30, priced at $1,755 found 22 hours ago

Cheap Flights to Winchester

Fall in love at first flight with your vacation to Winchester 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 Winchester on Hotwire, and you’ll be up, up, and on a getaway in no time.

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

Frequently Asked Questions About flights to Winchester

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Winchester 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 YOW airport.

What is the cheapest month to fly to Winchester?

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 Winchester are in July, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Winchester?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 15 to choose from for your flight to Winchester.

What airport is best to fly into Winchester?

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

How much are flights to Winchester?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Winchester on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $211, 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 Winchester?

The trick to saving a stack of cash on your flight to Winchester? 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 $211 right now, why wait?

Winchester Flight Information
Destination airport
Macdonald-Cartier Intl.
Destination airport IATA code
YOW
Roundtrip price
$211

Last Minute Hotel Deals in Winchester

Terrace Green Bed & Breakfast
Terrace Green Bed & Breakfast
3 out of 5
11952 County Road 43, North Dundas, ON
Stay at this 3-star B&B in North Dundas. Enjoy free breakfast, free WiFi, and free parking.
9.6/10 Exceptional! (102 reviews)
"Nice people, room was cool and bed was warm, very easy to find, very close to the city."

Reviewed on May 8, 2025

Get rates
Terrace Green Bed & Breakfast
Microtel by Wyndham Casselman
Microtel by Wyndham Casselman
3 out of 5
17 Rue Industriel, Casselman, ON
Stay at this 3-star golf hotel in Casselman. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attraction ...
8.8/10 Excellent! (850 reviews)
"Can hear people from above if people occupying the room and walking. Specifically at night."

Reviewed on May 19, 2025

Get rates
Microtel by Wyndham Casselman
SureStay Hotel by Best Western Kemptville
SureStay Hotel by Best Western Kemptville
2.5 out of 5
4022 County Road 43, North Grenville, ON
Book a stay at this business-friendly hotel in North Grenville. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff ...
8/10 Very Good! (450 reviews)
"Very clean, well-kept. Staff very good. Easy parking, very convenient for our family."

Reviewed on May 18, 2025

Get rates
SureStay Hotel by Best Western Kemptville
659 Parkview Ter
659 Parkview Ter
2 out of 5
659 Parkview Ter, Russell, ON
Stay at this guesthouse in Russell. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions W.E. Burton Conservation Area and Russell Public ...
9.2/10 Wonderful! (33 reviews)
"The place was clean, and everything are new. The owner also friendly"

Reviewed on May 21, 2025

Get rates
659 Parkview Ter
McIntosh Country Inn & Conference Centre in Canada
McIntosh Country Inn & Conference Centre in Canada
3.5 out of 5
12495 Highway 2 East, South Dundas, ON
Stay at this 3.5-star hotel in South Dundas. Enjoy free parking, an outdoor pool, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular ...
8.2/10 Very Good! (360 reviews)
"The cleaning lady started vacuuming at 7 in the morning and didn’t stop although it was Sunday. The heater was so loud we had to get up and turn it off. The room was in the lower level and had a musty smell. So we were ready to check out early."

Reviewed on May 15, 2025

Get rates
McIntosh Country Inn & Conference Centre in Canada
Kemptville Suites
Kemptville Suites
4 out of 5
103 Clothier St. East, North Grenville, ON
Stay at this 4-star hotel in North Grenville. Enjoy free WiFi, free parking, and onsite spa services. Popular attractions North Grenville Public Library - Kemptville ...
9.6/10 Exceptional! (243 reviews)
"Convenient location"

Reviewed on May 18, 2025

Get rates
Kemptville Suites
KC's Country Inn
KC's Country Inn
2.5 out of 5
984 Burton Rd., Russell, ON
Stay at this motel in Russell. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Alcide ...
7.4/10 Good! (303 reviews)
Clean, comfortable, convenient.
"Clean, comfortable bed, nicely redone bathroom. Looking for a place to sleep, it was good for me. Adjacent food truck and convenience store was helpful. Did not stay to sample the half-price breakfast."

Reviewed on May 15, 2025

Get rates
KC's Country Inn
Cedar Drive Inn
Cedar Drive Inn
3 out of 5
14990 Concession 10-11 Road, North Stormont, ON
Stay at this 3-star inn in North Stormont. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular ...
9/10 Wonderful! (84 reviews)
"Exelente servicio.. habitaciones super limpias y organizadas. 100/100"

Reviewed on May 18, 2025

Get rates
Cedar Drive Inn
See all 46 properties in Winchester
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.