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Winchester

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Winchester Flights as Low as $134

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

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Air Canada
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United
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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 February, 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 16 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 $134, 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 $134 right now, why wait?

Winchester Flight Information
Destination airport
Macdonald-Cartier Intl.
Destination airport IATA code
YOW
Roundtrip price
$134

Last Minute Hotel Deals in Winchester

Hard Rock Hotel & Casino Ottawa

Hard Rock Hotel & Casino Ottawa

4 out of 5
4837 Albion Road South Ottawa ON
Stay at this resort in Ottawa. Enjoy free WiFi, free parking, and 8 restaurants. Popular attractions Rideau Carleton Raceway and Ernst & Young Centre are located ...
9/10 Wonderful! (266 reviews)
Casino was lots of fun, meal was amazing and room clean and comfortable

Reviewed on Jan 17, 2026

Hard Rock Hotel & Casino Ottawa
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 Kemptville. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff ...
8/10 Very Good! (528 reviews)
Clean room, comfortable bed, simple breakfast, but qith several options.

Reviewed on Dec 29, 2025

SureStay Hotel by Best Western Kemptville
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 hotel in South Dundas. Enjoy free parking, an outdoor pool, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.2/10 Very Good! (465 reviews)
The ladies at the reception desk were very helpful, polite and kind. The food was really very good and the service was great.

Reviewed on Jan 12, 2026

McIntosh Country Inn & Conference Centre in Canada
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! (327 reviews)
C’est très bien comme aider à trouver des hôtels et des hébergements à bas prix.

Reviewed on Jan 7, 2026

KC's Country Inn
Kemptville Suites

Kemptville Suites

4 out of 5
103 Clothier St. East North Grenville ON
Stay at this hotel in Kemptville. Enjoy free WiFi, free parking, and onsite spa services. Popular attractions North Grenville Public Library - Kemptville Branch ...
9.6/10 Exceptional! (277 reviews)
very clean, felt like home, nice part of town, netflix,

Reviewed on Jan 2, 2026

Kemptville Suites
Bed & Stay

Bed & Stay

2 out of 5
659 Parkview Ter Russell ON
Stay at this guesthouse in Russell. Enjoy free WiFi, free parking, and a fireplace in the lobby. Popular attractions Keith M. Boyd Park and Parc de la Piscine ...
9.2/10 Wonderful! (59 reviews)
Clean house and great person to deal with. Very good and simple instructions for a smooth and nice stay.

Reviewed on Jan 12, 2026

Bed & Stay
Terrace Green Bed & Breakfast

Terrace Green Bed & Breakfast

3 out of 5
11952 County Road 43 North Dundas ON
Stay at this B&B in North Dundas. Enjoy free breakfast, free WiFi, and free parking.
9.6/10 Exceptional! (113 reviews)
The bed was exceptionally comfortable, Annette warm and inviting, and the breakfast delicious.

Reviewed on Nov 17, 2025

Terrace Green Bed & Breakfast
Cedar Drive Inn

Cedar Drive Inn

3 out of 5
14990 Concession 10-11 Road North Stormont ON
Stay at this inn in North Stormont. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (99 reviews)
clean room, staff stayed up to let me in after closing. Friendly and relaxing.

Reviewed on Nov 11, 2025

Cedar Drive Inn
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.