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Winchester

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Winchester Flights as Low as $515

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

Porter Airlines
Tue, Jul 7 - Mon, Jul 13
BNA
Nashville Intl.
YOW
Macdonald-Cartier Intl.
$515 Roundtrip, found 1 day ago
$515
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Tue, Jul 7 from Nashville Intl. to Macdonald-Cartier Intl., returning Mon, Jul 13, priced at $515 found 1 day ago
JetBlue Airways
Tue, Aug 18 - Tue, Aug 25
ATL
Hartsfield-Jackson Atlanta Intl.
YOW
Macdonald-Cartier Intl.
$553 Roundtrip, found 1 day ago
$553
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Aug 18 from Hartsfield-Jackson Atlanta Intl. to Macdonald-Cartier Intl., returning Tue, Aug 25, priced at $553 found 1 day ago
Air Canada
Sun, Sep 6 - Tue, Sep 8
ATL
Hartsfield-Jackson Atlanta Intl.
YOW
Macdonald-Cartier Intl.
$559 Roundtrip, found 6 days ago
$559
Roundtrip
found 6 days ago
Select Air Canada flight, departing Sun, Sep 6 from Hartsfield-Jackson Atlanta Intl. to Macdonald-Cartier Intl., returning Tue, Sep 8, priced at $559 found 6 days ago
Porter Airlines
Tue, Jul 7 - Mon, Jul 13
BNA
Nashville Intl.
YOW
Macdonald-Cartier Intl.
$561 Roundtrip, found 1 day ago
$561
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Tue, Jul 7 from Nashville Intl. to Macdonald-Cartier Intl., returning Mon, Jul 13, priced at $561 found 1 day ago
American Airlines
Tue, Aug 18 - Tue, Aug 25
BHM
Birmingham Intl.
YOW
Macdonald-Cartier Intl.
$592 Roundtrip, found 1 day ago
$592
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Aug 18 from Birmingham Intl. to Macdonald-Cartier Intl., returning Tue, Aug 25, priced at $592 found 1 day ago
United
Sat, Aug 15 - Wed, Aug 26
BHM
Birmingham Intl.
YOW
Macdonald-Cartier Intl.
$603 Roundtrip, found 1 day ago
$603
Roundtrip
found 1 day ago
Select United flight, departing Sat, Aug 15 from Birmingham Intl. to Macdonald-Cartier Intl., returning Wed, Aug 26, priced at $603 found 1 day ago
American Airlines
Tue, Oct 20 - Sat, Oct 24
BHM
Birmingham Intl.
YOW
Macdonald-Cartier Intl.
$638 Roundtrip, found 6 days ago
$638
Roundtrip
found 6 days ago
Select American Airlines flight, departing Tue, Oct 20 from Birmingham Intl. to Macdonald-Cartier Intl., returning Sat, Oct 24, priced at $638 found 6 days ago
Delta
Fri, Aug 21 - Sat, Aug 29
BHM
Birmingham Intl.
YOW
Macdonald-Cartier Intl.
$705 Roundtrip, found 6 days ago
$705
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Aug 21 from Birmingham Intl. to Macdonald-Cartier Intl., returning Sat, Aug 29, priced at $705 found 6 days ago
Air Transat
Fri, Jul 3 - Sat, Jul 18
AMS
Schiphol
YOW
Macdonald-Cartier Intl.
$887 Roundtrip, found 4 hours ago
$887
Roundtrip
found 4 hours ago
Select Air Transat flight, departing Fri, Jul 3 from Schiphol to Macdonald-Cartier Intl., returning Sat, Jul 18, priced at $887 found 4 hours ago
WestJet
Tue, Oct 20 - Tue, Oct 27
BHM
Birmingham Intl.
YOW
Macdonald-Cartier Intl.
$1,183 Roundtrip, found 6 days ago
$1,183
Roundtrip
found 6 days ago
Select WestJet flight, departing Tue, Oct 20 from Birmingham Intl. to Macdonald-Cartier Intl., returning Tue, Oct 27, priced at $1,183 found 6 days ago
TAP Portugal
Tue, Jun 30 - Tue, Jul 21
AMS
Schiphol
YOW
Macdonald-Cartier Intl.
$1,208 Roundtrip, found 12 hours ago
$1,208
Roundtrip
found 12 hours ago
Select TAP Portugal flight, departing Tue, Jun 30 from Schiphol to Macdonald-Cartier Intl., returning Tue, Jul 21, priced at $1,208 found 12 hours ago
LOT-Polish Airlines
Fri, Jul 3 - Sat, Jul 18
AMS
Schiphol
YOW
Macdonald-Cartier Intl.
$1,420 Roundtrip, found 4 hours ago
$1,420
Roundtrip
found 4 hours ago
Select LOT-Polish Airlines flight, departing Fri, Jul 3 from Schiphol to Macdonald-Cartier Intl., returning Sat, Jul 18, priced at $1,420 found 4 hours ago
Lufthansa
Fri, Jul 3 - Sat, Jul 18
AMS
Schiphol
YOW
Macdonald-Cartier Intl.
$1,500 Roundtrip, found 4 hours ago
$1,500
Roundtrip
found 4 hours ago
Select Lufthansa flight, departing Fri, Jul 3 from Schiphol to Macdonald-Cartier Intl., returning Sat, Jul 18, priced at $1,500 found 4 hours ago
KLM
Tue, Jun 30 - Thu, Jul 16
AMS
Schiphol
XDS
Ottawa Train Station
$1,503 Roundtrip, found 5 days ago
$1,503
Roundtrip
found 5 days ago
Select KLM flight, departing Tue, Jun 30 from Schiphol to Ottawa Train Station, returning Thu, Jul 16, priced at $1,503 found 5 days ago
Swiss International Air Lines
Fri, Jul 3 - Sat, Jul 18
AMS
Schiphol
YOW
Macdonald-Cartier Intl.
$1,513 Roundtrip, found 4 hours ago
$1,513
Roundtrip
found 4 hours ago
Select Swiss International Air Lines flight, departing Fri, Jul 3 from Schiphol to Macdonald-Cartier Intl., returning Sat, Jul 18, priced at $1,513 found 4 hours ago
KLM
Sat, Jul 4 - Thu, Jul 16
AMS
Schiphol
XDS
Ottawa Train Station
$1,593 Roundtrip, found 5 days ago
$1,593
Roundtrip
found 5 days ago
Select KLM flight, departing Sat, Jul 4 from Schiphol to Ottawa Train Station, returning Thu, Jul 16, priced at $1,593 found 5 days 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 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 $515, 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 $515 right now, why wait?

Winchester Flight Information
Destination airport
Macdonald-Cartier Intl.
Destination airport IATA code
YOW
Roundtrip price
$886

Last Minute Hotel Deals in Winchester

Hard Rock Hotel & Casino Ottawa

Hard Rock Hotel & Casino Ottawa

4.5 out of 5
4837 Albion Road South Ottawa ON
Book a stay at this luxury resort in Ottawa. Enjoy free WiFi, free parking, and 8 restaurants. Popular attractions Rideau Carleton Raceway and Ernst & Young ...
9.2/10 Wonderful! (503 reviews)
"Great staff starting with check in Helpful. Comfortable beds and furniture. Very well maintained."

Reviewed on Jun 27, 2026

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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! (577 reviews)
"Could use a better breakfast. Just toast, yogurt and"

Reviewed on Jun 22, 2026

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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 ...
8.4/10 Very Good! (483 reviews)
"The room was comfortable, clean and quiet. Decor in the room was a bit dated, looked like not too recently renovated, but satisfactory and consistent with the character of the property. Front desk and restaurant staff were friendly and helpful. Restaurant food was good pub fare and fairly ..."

Reviewed on Jun 28, 2026

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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 hotel in Kemptville. Enjoy free WiFi, free parking, and onsite spa services. Popular attractions North Grenville Public Library - Kemptville Branch ...
9.6/10 Exceptional! (300 reviews)
"Yes the AC was great. Would be nice to be able to open a window to get fresh air. The amenities such as robes and shampoo and teas and coffee were very good quality. Great response when i needed to call about the door code. Snacks heslthier than duritos would be nice but over all the place was great. ..."

Reviewed on Jun 18, 2026

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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! (63 reviews)
"Lovely home, clean, spacious, bright, great location for us. Convenient. Staff were responsive to questions. Our room and ensuite was spacious. Parking was not an issue. Nice neighbourhood with a walking path around the water reservoir."

Reviewed on Apr 22, 2026

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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! (121 reviews)
"It was a welcomed stay as both my husband and I really needed a night away to relax. The property is clean enough and I wouldn't be afraid to stay again, but let's say my house after a clean on Saturday is much cleaner. The owner wasn't going out of her way to accommodate but she was kind. The breakfast ..."

Reviewed on Jun 20, 2026

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Terrace Green Bed & Breakfast
Doran Bay Resort

Doran Bay Resort

2.5 out of 5
11128 County Road 2 South Dundas ON
Book a stay at this beach cottage in South Dundas. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Iroquois Golf Club and Iroquois Beach ...
7.8/10 Good! (25 reviews)
"I thought the property was great for the value. It was clean, and well prepared. Everything was very well thought out, and brillianty laid out. I misread that there was a children's pool and a beach, but there is a beautiful beach 1km away I would definitely stay here again. Oh and we relived our ..."

Reviewed on Jun 28, 2026

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Doran Bay Resort
Cedar Drive Inn

Cedar Drive Inn

3 out of 5
14990 Concession 10-11 Road North Stormont ON
Stay at this guesthouse in North Stormont. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular ...
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Cedar Drive Inn
See all 48 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.