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Winchester

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Winchester Flights as Low as $341

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

Air Canada
Sat, Apr 26 - Sun, Apr 27
IAD
Washington Dulles Intl.
YOW
Macdonald-Cartier Intl.
$341 Roundtrip, found 23 hours ago
$341
Roundtrip
found 23 hours ago
Select Air Canada flight, departing Sat, Apr 26 from Washington Dulles Intl. to Macdonald-Cartier Intl., returning Sun, Apr 27, priced at $341 found 23 hours ago
Air Canada
Sat, Apr 26 - Mon, Apr 28
IAD
Washington Dulles Intl.
YOW
Macdonald-Cartier Intl.
$391 Roundtrip, found 1 day ago
$391
Roundtrip
found 1 day ago
Select Air Canada flight, departing Sat, Apr 26 from Washington Dulles Intl. to Macdonald-Cartier Intl., returning Mon, Apr 28, priced at $391 found 1 day ago
Air Canada
Sat, Apr 26 - Tue, Apr 29
IAD
Washington Dulles Intl.
YOW
Macdonald-Cartier Intl.
$393 Roundtrip, found 23 hours ago
$393
Roundtrip
found 23 hours ago
Select Air Canada flight, departing Sat, Apr 26 from Washington Dulles Intl. to Macdonald-Cartier Intl., returning Tue, Apr 29, priced at $393 found 23 hours ago
Air Canada
Sat, Apr 26 - Mon, Apr 28
IAD
Washington Dulles Intl.
YOW
Macdonald-Cartier Intl.
$396 Roundtrip, found 1 day ago
$396
Roundtrip
found 1 day ago
Select Air Canada flight, departing Sat, Apr 26 from Washington Dulles Intl. to Macdonald-Cartier Intl., returning Mon, Apr 28, priced at $396 found 1 day ago
Air Canada
Sat, Apr 26 - Mon, Apr 28
IAD
Washington Dulles Intl.
YOW
Macdonald-Cartier Intl.
$398 Roundtrip, found 1 day ago
$398
Roundtrip
found 1 day ago
Select Air Canada flight, departing Sat, Apr 26 from Washington Dulles Intl. to Macdonald-Cartier Intl., returning Mon, Apr 28, priced at $398 found 1 day ago
Air Canada
Sat, Apr 26 - Sun, Apr 27
IAD
Washington Dulles Intl.
YOW
Macdonald-Cartier Intl.
$399 Roundtrip, found 23 hours ago
$399
Roundtrip
found 23 hours ago
Select Air Canada flight, departing Sat, Apr 26 from Washington Dulles Intl. to Macdonald-Cartier Intl., returning Sun, Apr 27, priced at $399 found 23 hours ago
Air Canada
Tue, Apr 29 - Tue, Apr 29
DCA
Ronald Reagan Washington National
YOW
Macdonald-Cartier Intl.
$404 Roundtrip, found 1 day ago
$404
Roundtrip
found 1 day ago
Select Air Canada flight, departing Tue, Apr 29 from Ronald Reagan Washington National to Macdonald-Cartier Intl., returning Tue, Apr 29, priced at $404 found 1 day ago
Porter Airlines
Sat, Apr 26 - Mon, Apr 28
IAD
Washington Dulles Intl.
YOW
Macdonald-Cartier Intl.
$409 Roundtrip, found 1 day ago
$409
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Sat, Apr 26 from Washington Dulles Intl. to Macdonald-Cartier Intl., returning Mon, Apr 28, priced at $409 found 1 day ago
Porter Airlines
Thu, Apr 24 - Sun, Apr 27
IAD
Washington Dulles Intl.
YOW
Macdonald-Cartier Intl.
$414 Roundtrip, found 23 hours ago
$414
Roundtrip
found 23 hours ago
Select Porter Airlines flight, departing Thu, Apr 24 from Washington Dulles Intl. to Macdonald-Cartier Intl., returning Sun, Apr 27, priced at $414 found 23 hours ago
Air Canada
Tue, Apr 29 - Tue, Apr 29
IAD
Washington Dulles Intl.
YOW
Macdonald-Cartier Intl.
$421 Roundtrip, found 23 hours ago
$421
Roundtrip
found 23 hours ago
Select Air Canada flight, departing Tue, Apr 29 from Washington Dulles Intl. to Macdonald-Cartier Intl., returning Tue, Apr 29, priced at $421 found 23 hours ago
Porter Airlines
Sun, Apr 27 - Mon, Apr 28
IAD
Washington Dulles Intl.
YOW
Macdonald-Cartier Intl.
$431 Roundtrip, found 23 hours ago
$431
Roundtrip
found 23 hours ago
Select Porter Airlines flight, departing Sun, Apr 27 from Washington Dulles Intl. to Macdonald-Cartier Intl., returning Mon, Apr 28, priced at $431 found 23 hours ago
Porter Airlines
Mon, Apr 21 - Sat, Apr 26
YQM
Greater Moncton Intl.
YOW
Macdonald-Cartier Intl.
$505 Roundtrip, found 1 day ago
$505
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Mon, Apr 21 from Greater Moncton Intl. to Macdonald-Cartier Intl., returning Sat, Apr 26, priced at $505 found 1 day ago
Air Transat
Wed, Apr 16 - Sat, Apr 26
YQM
Greater Moncton Intl.
YOW
Macdonald-Cartier Intl.
$524 Roundtrip, found 2 days ago
$524
Roundtrip
found 2 days ago
Select Air Transat flight, departing Wed, Apr 16 from Greater Moncton Intl. to Macdonald-Cartier Intl., returning Sat, Apr 26, priced at $524 found 2 days ago
WestJet
Thu, Apr 24 - Wed, Apr 30
YXX
Abbotsford Intl.
YOW
Macdonald-Cartier Intl.
$545 Roundtrip, found 3 days ago
$545
Roundtrip
found 3 days ago
Select WestJet flight, departing Thu, Apr 24 from Abbotsford Intl. to Macdonald-Cartier Intl., returning Wed, Apr 30, priced at $545 found 3 days ago
United
Sat, Apr 26 - Tue, Apr 29
DCA
Ronald Reagan Washington National
YOW
Macdonald-Cartier Intl.
$598 Roundtrip, found 1 day ago
$598
Roundtrip
found 1 day ago
Select United flight, departing Sat, Apr 26 from Ronald Reagan Washington National to Macdonald-Cartier Intl., returning Tue, Apr 29, priced at $598 found 1 day ago
WestJet
Sun, Apr 27 - Tue, Apr 29
YVR
Vancouver Intl.
YOW
Macdonald-Cartier Intl.
$604 Roundtrip, found 3 days ago
$604
Roundtrip
found 3 days ago
Select WestJet flight, departing Sun, Apr 27 from Vancouver Intl. to Macdonald-Cartier Intl., returning Tue, Apr 29, priced at $604 found 3 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 April, 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 $341, 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 $341 right now, why wait?

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
The price is $94 per night from Apr 14 to Apr 15
$94
includes taxes & fees
Apr 14 - Apr 15
Stay at this 3-star B&B in North Dundas. Enjoy free breakfast, free WiFi, and free parking.
9.6/10 Exceptional! (100 reviews)
"Lovely stay. Great gas fireplace"

Reviewed on Dec 8, 2024

Terrace Green Bed & Breakfast
Microtel by Wyndham Casselman
Microtel by Wyndham Casselman
3 out of 5
17 Rue Industriel, Casselman, ON
The price is $118 per night from Apr 20 to Apr 21
$118
includes taxes & fees
Apr 20 - Apr 21
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! (820 reviews)
"This was such a nice hotel. Better than some hotels that are twice the price. Comfy beds."

Reviewed on Apr 8, 2025

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
The price is $95 per night from Apr 16 to Apr 17
$95
includes taxes & fees
Apr 16 - Apr 17
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! (442 reviews)
"The only thing I did not like was the smell of the water."

Reviewed on Apr 9, 2025

SureStay Hotel by Best Western Kemptville
659 Parkview Ter
659 Parkview Ter
2 out of 5
659 Parkview Ter, Russell, ON
The price is $62 per night from Apr 14 to Apr 15
$62
includes taxes & fees
Apr 14 - Apr 15
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! (21 reviews)
"Good place. Very clean and quiet."

Reviewed on Apr 7, 2025

659 Parkview Ter
Kemptville Suites
Kemptville Suites
4 out of 5
103 Clothier St. East, North Grenville, ON
The price is $195 per night from Apr 14 to Apr 15
$195
includes taxes & fees
Apr 14 - Apr 15
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! (237 reviews)
"Loved the stone walls and wooden beams. What character! Also loved the kitchenette with coffee, tea and snacks provided. Bed and pillows were very comfortable. Would recommend to others. Thank you."

Reviewed on Apr 7, 2025

Kemptville Suites
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
The price is $162 per night from Apr 14 to Apr 15
$162
includes taxes & fees
Apr 14 - Apr 15
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! (358 reviews)
"A"

Reviewed on Apr 6, 2025

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! (300 reviews)
"Good location and friendly staff"

Reviewed on Dec 31, 2024

Get rates
KC's Country Inn
Cedar Drive Inn
Cedar Drive Inn
3 out of 5
14990 Concession 10-11 Road, North Stormont, ON
The price is $111 per night from Apr 14 to Apr 15
$111
includes taxes & fees
Apr 14 - Apr 15
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! (82 reviews)
Cute little inn
"Cute little inn outside Ottawa!"

Reviewed on Dec 6, 2024

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.