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Winchester

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Winchester Flights as Low as $315

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

Porter Airlines
Mon, Aug 31 - Mon, Sep 7
FLL
Fort Lauderdale - Hollywood Intl.
YOW
Macdonald-Cartier Intl.
$315 Roundtrip, found 23 hours ago
$315
Roundtrip
found 23 hours ago
Select Porter Airlines flight, departing Mon, Aug 31 from Fort Lauderdale - Hollywood Intl. to Macdonald-Cartier Intl., returning Mon, Sep 7, priced at $315 found 23 hours ago
Porter Airlines
Mon, Aug 31 - Mon, Sep 7
FLL
Fort Lauderdale - Hollywood Intl.
YOW
Macdonald-Cartier Intl.
$335 Roundtrip, found 23 hours ago
$335
Roundtrip
found 23 hours ago
Select Porter Airlines flight, departing Mon, Aug 31 from Fort Lauderdale - Hollywood Intl. to Macdonald-Cartier Intl., returning Mon, Sep 7, priced at $335 found 23 hours ago
Air Canada
Tue, Oct 20 - Sun, Oct 25
FLL
Fort Lauderdale - Hollywood Intl.
YOW
Macdonald-Cartier Intl.
$339 Roundtrip, found 21 hours ago
$339
Roundtrip
found 21 hours ago
Select Air Canada flight, departing Tue, Oct 20 from Fort Lauderdale - Hollywood Intl. to Macdonald-Cartier Intl., returning Sun, Oct 25, priced at $339 found 21 hours ago
Porter Airlines
Mon, Aug 31 - Mon, Sep 7
FLL
Fort Lauderdale - Hollywood Intl.
YOW
Macdonald-Cartier Intl.
$348 Roundtrip, found 23 hours ago
$348
Roundtrip
found 23 hours ago
Select Porter Airlines flight, departing Mon, Aug 31 from Fort Lauderdale - Hollywood Intl. to Macdonald-Cartier Intl., returning Mon, Sep 7, priced at $348 found 23 hours ago
Air Canada
Tue, Oct 20 - Fri, Oct 30
FLL
Fort Lauderdale - Hollywood Intl.
YOW
Macdonald-Cartier Intl.
$353 Roundtrip, found 21 hours ago
$353
Roundtrip
found 21 hours ago
Select Air Canada flight, departing Tue, Oct 20 from Fort Lauderdale - Hollywood Intl. to Macdonald-Cartier Intl., returning Fri, Oct 30, priced at $353 found 21 hours ago
Air Canada
Tue, Oct 20 - Sun, Oct 25
FLL
Fort Lauderdale - Hollywood Intl.
YOW
Macdonald-Cartier Intl.
$365 Roundtrip, found 21 hours ago
$365
Roundtrip
found 21 hours ago
Select Air Canada flight, departing Tue, Oct 20 from Fort Lauderdale - Hollywood Intl. to Macdonald-Cartier Intl., returning Sun, Oct 25, priced at $365 found 21 hours ago
Porter Airlines
Mon, Aug 31 - Mon, Sep 7
FLL
Fort Lauderdale - Hollywood Intl.
YOW
Macdonald-Cartier Intl.
$369 Roundtrip, found 23 hours ago
$369
Roundtrip
found 23 hours ago
Select Porter Airlines flight, departing Mon, Aug 31 from Fort Lauderdale - Hollywood Intl. to Macdonald-Cartier Intl., returning Mon, Sep 7, priced at $369 found 23 hours ago
Porter Airlines
Mon, Aug 31 - Mon, Sep 7
FLL
Fort Lauderdale - Hollywood Intl.
YOW
Macdonald-Cartier Intl.
$376 Roundtrip, found 23 hours ago
$376
Roundtrip
found 23 hours ago
Select Porter Airlines flight, departing Mon, Aug 31 from Fort Lauderdale - Hollywood Intl. to Macdonald-Cartier Intl., returning Mon, Sep 7, priced at $376 found 23 hours ago
Air Canada
Tue, Oct 20 - Fri, Oct 30
FLL
Fort Lauderdale - Hollywood Intl.
YOW
Macdonald-Cartier Intl.
$379 Roundtrip, found 21 hours ago
$379
Roundtrip
found 21 hours ago
Select Air Canada flight, departing Tue, Oct 20 from Fort Lauderdale - Hollywood Intl. to Macdonald-Cartier Intl., returning Fri, Oct 30, priced at $379 found 21 hours ago
Air Canada
Tue, Oct 20 - Sun, Oct 25
FLL
Fort Lauderdale - Hollywood Intl.
YOW
Macdonald-Cartier Intl.
$379 Roundtrip, found 21 hours ago
$379
Roundtrip
found 21 hours ago
Select Air Canada flight, departing Tue, Oct 20 from Fort Lauderdale - Hollywood Intl. to Macdonald-Cartier Intl., returning Sun, Oct 25, priced at $379 found 21 hours ago
Porter Airlines
Mon, Aug 31 - Mon, Sep 7
FLL
Fort Lauderdale - Hollywood Intl.
YOW
Macdonald-Cartier Intl.
$430 Roundtrip, found 23 hours ago
$430
Roundtrip
found 23 hours ago
Select Porter Airlines flight, departing Mon, Aug 31 from Fort Lauderdale - Hollywood Intl. to Macdonald-Cartier Intl., returning Mon, Sep 7, priced at $430 found 23 hours ago
Air Canada
Wed, Jul 22 - Wed, Jul 22
MCO
Orlando Intl.
YOW
Macdonald-Cartier Intl.
$516 Roundtrip, found 1 day ago
$516
Roundtrip
found 1 day ago
Select Air Canada flight, departing Wed, Jul 22 from Orlando Intl. to Macdonald-Cartier Intl., returning Wed, Jul 22, priced at $516 found 1 day ago
United
Thu, Jul 23 - Thu, Jul 23
MCO
Orlando Intl.
YOW
Macdonald-Cartier Intl.
$520 Roundtrip, found 1 day ago
$520
Roundtrip
found 1 day ago
Select United flight, departing Thu, Jul 23 from Orlando Intl. to Macdonald-Cartier Intl., returning Thu, Jul 23, priced at $520 found 1 day ago
American Airlines
Mon, Aug 31 - Mon, Sep 7
FLL
Fort Lauderdale - Hollywood Intl.
YOW
Macdonald-Cartier Intl.
$643 Roundtrip, found 23 hours ago
$643
Roundtrip
found 23 hours ago
Select American Airlines flight, departing Mon, Aug 31 from Fort Lauderdale - Hollywood Intl. to Macdonald-Cartier Intl., returning Mon, Sep 7, priced at $643 found 23 hours ago
WestJet
Tue, Oct 20 - Sun, Oct 25
FLL
Fort Lauderdale - Hollywood Intl.
YOW
Macdonald-Cartier Intl.
$823 Roundtrip, found 21 hours ago
$823
Roundtrip
found 21 hours ago
Select WestJet flight, departing Tue, Oct 20 from Fort Lauderdale - Hollywood Intl. to Macdonald-Cartier Intl., returning Sun, Oct 25, priced at $823 found 21 hours ago
Air Transat
Mon, Aug 31 - Mon, Sep 7
FLL
Fort Lauderdale - Hollywood Intl.
YOW
Macdonald-Cartier Intl.
$865 Roundtrip, found 23 hours ago
$865
Roundtrip
found 23 hours ago
Select Air Transat flight, departing Mon, Aug 31 from Fort Lauderdale - Hollywood Intl. to Macdonald-Cartier Intl., returning Mon, Sep 7, priced at $865 found 23 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 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 $315, 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 $315 right now, why wait?

Winchester Flight Information
Destination airport
Macdonald-Cartier Intl.
Destination airport IATA code
YOW
Roundtrip price
$315

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! (537 reviews)
"The worst experience ever. Do not book here."

Reviewed on Jul 18, 2026

Get rates
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! (585 reviews)
"It's a place for when you in a long journey to stop by but it was ok the cleaning staff 👌 specially the lady"

Reviewed on Jul 18, 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! (488 reviews)
"It’s so close to Upper Canada Village"

Reviewed on Jul 15, 2026

Get rates
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 ...
7.6/10 Good! (339 reviews)
"If you want an experience ….. pay 2 to 3 times the cost and stay in Ottawa. If you want a basic, clean, quiet, safe covenantally located place to stay over this works. First of all cost Really cheap… about as low as you will find. Cleanliness…. Top notch. Not fancy at all but functional. The whole ..."

Reviewed on Jul 13, 2026

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KC's Country Inn
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
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 ...
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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! (123 reviews)
"Good"

Reviewed on Jul 1, 2026

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Terrace Green Bed & Breakfast
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.