Search Cheap Flights to
Winchester

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

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 , 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  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 , 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  right now, why wait?

Winchester Flight Information
Destination airport
Winchester
Destination airport IATA code
YOW

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! (200 reviews)
Casino would beat better and busier with a poker room. Staff was well trained, polite and noticibaly courteous.

Reviewed on Nov 18, 2025

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! (519 reviews)
Yes

Reviewed on Nov 16, 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! (452 reviews)
The property was definitely older but had a lot of charm. The room was equipped with a small bar fridge, TV and a desk. There was a small dresser, space to hang clothes, iron and ironing board. The bathroom was quite small but worked. The restaurant was great and we really enjoyed the Saturday night ...

Reviewed on Nov 16, 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! (322 reviews)
Les canalisations étaient bouchées. L'eau s'évacuait très difficilement dans la douche.

Reviewed on Sep 21, 2025

KC's Country 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! (56 reviews)
The place looks very new and it’s clean, the Moazzam was super good and he is reachable 24/7. The place is surrounded by great nature and it is very quiet and cool place to relax and enjoy your stay.

Reviewed on Oct 27, 2025

Bed & Stay
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! (272 reviews)
Our suite was great for us. It was comfortable and well appointed. The weather was wet and rainy so we really enjoyed the gas fireplace. One suggestion would be to put a lamp in the sitting area. For people with "old eyes" it was hard to read printed material on the couch.

Reviewed on Nov 4, 2025

Kemptville Suites
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! (95 reviews)
clean room, staff stayed up to let me in after closing. Friendly and relaxing.

Reviewed on Nov 11, 2025

Cedar Drive Inn
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
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.