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Winchester

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Winchester Flights as Low as $1,221

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

Air France
Mon, Aug 3 - Fri, Aug 28
NBO
Jomo Kenyatta Intl.
YOW
Macdonald-Cartier Intl.
$1,221 Roundtrip, found 1 day ago
$1,221
Roundtrip
found 1 day ago
Select Air France flight, departing Mon, Aug 3 from Jomo Kenyatta Intl. to Macdonald-Cartier Intl., returning Fri, Aug 28, priced at $1,221 found 1 day ago
Air France
Mon, Aug 3 - Fri, Aug 28
NBO
Jomo Kenyatta Intl.
YOW
Macdonald-Cartier Intl.
$1,222 Roundtrip, found 1 day ago
$1,222
Roundtrip
found 1 day ago
Select Air France flight, departing Mon, Aug 3 from Jomo Kenyatta Intl. to Macdonald-Cartier Intl., returning Fri, Aug 28, priced at $1,222 found 1 day ago
Brussels Airlines
Mon, Aug 3 - Thu, Aug 27
NBO
Jomo Kenyatta Intl.
YOW
Macdonald-Cartier Intl.
$1,243 Roundtrip, found 4 days ago
$1,243
Roundtrip
found 4 days ago
Select Brussels Airlines flight, departing Mon, Aug 3 from Jomo Kenyatta Intl. to Macdonald-Cartier Intl., returning Thu, Aug 27, priced at $1,243 found 4 days ago
Air France
Mon, Aug 3 - Fri, Aug 28
NBO
Jomo Kenyatta Intl.
YOW
Macdonald-Cartier Intl.
$1,271 Roundtrip, found 1 day ago
$1,271
Roundtrip
found 1 day ago
Select Air France flight, departing Mon, Aug 3 from Jomo Kenyatta Intl. to Macdonald-Cartier Intl., returning Fri, Aug 28, priced at $1,271 found 1 day ago
Brussels Airlines
Mon, Aug 3 - Thu, Aug 27
NBO
Jomo Kenyatta Intl.
YOW
Macdonald-Cartier Intl.
$1,271 Roundtrip, found 4 days ago
$1,271
Roundtrip
found 4 days ago
Select Brussels Airlines flight, departing Mon, Aug 3 from Jomo Kenyatta Intl. to Macdonald-Cartier Intl., returning Thu, Aug 27, priced at $1,271 found 4 days ago
United
Mon, Aug 10 - Tue, Sep 1
NBO
Jomo Kenyatta Intl.
YOW
Macdonald-Cartier Intl.
$1,284 Roundtrip, found 1 day ago
$1,284
Roundtrip
found 1 day ago
Select United flight, departing Mon, Aug 10 from Jomo Kenyatta Intl. to Macdonald-Cartier Intl., returning Tue, Sep 1, priced at $1,284 found 1 day ago
Kenya Airways
Sun, Aug 9 - Thu, Aug 27
NBO
Jomo Kenyatta Intl.
YOW
Macdonald-Cartier Intl.
$1,286 Roundtrip, found 4 days ago
$1,286
Roundtrip
found 4 days ago
Select Kenya Airways flight, departing Sun, Aug 9 from Jomo Kenyatta Intl. to Macdonald-Cartier Intl., returning Thu, Aug 27, priced at $1,286 found 4 days ago
United
Fri, Jul 31 - Wed, Sep 2
NBO
Jomo Kenyatta Intl.
YOW
Macdonald-Cartier Intl.
$1,288 Roundtrip, found 1 day ago
$1,288
Roundtrip
found 1 day ago
Select United flight, departing Fri, Jul 31 from Jomo Kenyatta Intl. to Macdonald-Cartier Intl., returning Wed, Sep 2, priced at $1,288 found 1 day ago
Air France
Fri, Jul 31 - Sun, Aug 30
NBO
Jomo Kenyatta Intl.
YOW
Macdonald-Cartier Intl.
$1,296 Roundtrip, found 1 day ago
$1,296
Roundtrip
found 1 day ago
Select Air France flight, departing Fri, Jul 31 from Jomo Kenyatta Intl. to Macdonald-Cartier Intl., returning Sun, Aug 30, priced at $1,296 found 1 day ago
Air Canada
Fri, Jul 31 - Tue, Sep 1
NBO
Jomo Kenyatta Intl.
YOW
Macdonald-Cartier Intl.
$1,326 Roundtrip, found 4 days ago
$1,326
Roundtrip
found 4 days ago
Select Air Canada flight, departing Fri, Jul 31 from Jomo Kenyatta Intl. to Macdonald-Cartier Intl., returning Tue, Sep 1, priced at $1,326 found 4 days ago
KLM
Fri, Jul 31 - Wed, Sep 2
NBO
Jomo Kenyatta Intl.
YOW
Macdonald-Cartier Intl.
$1,339 Roundtrip, found 1 day ago
$1,339
Roundtrip
found 1 day ago
Select KLM flight, departing Fri, Jul 31 from Jomo Kenyatta Intl. to Macdonald-Cartier Intl., returning Wed, Sep 2, priced at $1,339 found 1 day ago
United
Mon, Aug 10 - Tue, Sep 1
NBO
Jomo Kenyatta Intl.
YOW
Macdonald-Cartier Intl.
$1,364 Roundtrip, found 1 day ago
$1,364
Roundtrip
found 1 day ago
Select United flight, departing Mon, Aug 10 from Jomo Kenyatta Intl. to Macdonald-Cartier Intl., returning Tue, Sep 1, priced at $1,364 found 1 day ago
Air France
Sun, Aug 9 - Mon, Aug 31
NBO
Jomo Kenyatta Intl.
XDS
Ottawa Train Station
$1,407 Roundtrip, found 4 days ago
$1,407
Roundtrip
found 4 days ago
Select Air France flight, departing Sun, Aug 9 from Jomo Kenyatta Intl. to Ottawa Train Station, returning Mon, Aug 31, priced at $1,407 found 4 days ago
Lufthansa
Mon, Aug 10 - Tue, Sep 1
NBO
Jomo Kenyatta Intl.
YOW
Macdonald-Cartier Intl.
$1,635 Roundtrip, found 1 day ago
$1,635
Roundtrip
found 1 day ago
Select Lufthansa flight, departing Mon, Aug 10 from Jomo Kenyatta Intl. to Macdonald-Cartier Intl., returning Tue, Sep 1, priced at $1,635 found 1 day ago
Brussels Airlines
Mon, Aug 10 - Sun, Aug 30
NBO
Jomo Kenyatta Intl.
YOW
Macdonald-Cartier Intl.
$1,783 Roundtrip, found 1 day ago
$1,783
Roundtrip
found 1 day ago
Select Brussels Airlines flight, departing Mon, Aug 10 from Jomo Kenyatta Intl. to Macdonald-Cartier Intl., returning Sun, Aug 30, priced at $1,783 found 1 day ago
British Airways
Wed, Aug 5 - Sat, Aug 29
NBO
Jomo Kenyatta Intl.
YOW
Macdonald-Cartier Intl.
$2,932 Roundtrip, found 1 day ago
$2,932
Roundtrip
found 1 day ago
Select British Airways flight, departing Wed, Aug 5 from Jomo Kenyatta Intl. to Macdonald-Cartier Intl., returning Sat, Aug 29, priced at $2,932 found 1 day 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 August, 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 $1,221, 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 $1,221 right now, why wait?

Winchester Flight Information
Destination airport
Macdonald-Cartier Intl.
Destination airport IATA code
YOW
Roundtrip price
$339

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! (551 reviews)
"Clean room. Horrible view of rooftop heating and air conditioning units. Casino was nice. Restaurants on the property were convenient."

Reviewed on Jul 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! (589 reviews)
"Was very pleased with the motel we were able to bring our dog.Got a corner room by the handicap parking spot. The check in personel were most helpful and helped us fix some unfortunate booking on our part."

Reviewed on Jul 27, 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! (493 reviews)
"Staff were very friendly but rooms were old and in need of upgrading. Rooms were expensive for what you get. Meals qere expensive in the restaurant"

Reviewed on Jul 27, 2026

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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 ...
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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! (316 reviews)
"The electronic door lock didn't work when we arrived. Hence, we spend quite sometime to open the door. The next day, we could not open the door from inside. I think the door is sticking against the door frame. Because it has an electronic lock, it’s hard to tell whether the door is actually locked ..."

Reviewed on Jul 28, 2026

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Kemptville Suites
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! (26 reviews)
"This place is perfect for a family getaway especially for people with kids. Our kids loved the large open space and the playground as well as the pool. It was really lovely and everyone was very friendly and respectful. The hosts were also very friendly and accommodating as well. This is perfect ..."

Reviewed on Jul 5, 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
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
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.