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Winchester

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Winchester Flights as Low as $162

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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 LEX 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 13 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 Blue Grass 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 $162, 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 $162 right now, why wait?

Winchester Flight Information
Destination airport
Blue Grass
Destination airport IATA code
LEX
Roundtrip price
$162

Last Minute Hotel Deals in Winchester

Baymont by Wyndham Winchester
Baymont by Wyndham Winchester
2.5 out of 5
960 Interstate Dr, Winchester, KY
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
7/10 Good! (718 reviews)
"Quick stay after delayed flight. It had what we needed. Free breakfast that we were not expecting"

Reviewed on Jul 4, 2025

Baymont by Wyndham Winchester
Spark by Hilton Lexington Hamburg
Spark by Hilton Lexington Hamburg
2.5 out of 5
2381 Buena Vista Rd, Lexington, KY
Book a stay at this business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
8.8/10 Excellent! (49 reviews)
Great stay, will be back again
"Nice property, and well cared for. The breakfast offerings may have included a better fruit selection before I came down. That would be the only improvement I would suggest."

Reviewed on Jul 10, 2025

Spark by Hilton Lexington Hamburg
Quality Inn Lexington -Horse Park
Quality Inn Lexington -Horse Park
2.5 out of 5
1938 Stanton Way, Bldg A, Lexington, KY
Book a stay at this golf hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
8.2/10 Very Good! (1,629 reviews)
"Great to just get rest to hop back on the road."

Reviewed on Jul 8, 2025

Quality Inn Lexington -Horse Park
Elwood Hotel & Suites
Elwood Hotel & Suites
4 out of 5
444 Parkway Drive, Lexington, KY
Stay at this 4-star hotel in Lexington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our ...
9.2/10 Wonderful! (1,000 reviews)
"The breakfast was fantastic, murals everywhere and overall quiet"

Reviewed on Jul 8, 2025

Elwood Hotel & Suites
Hilton Lexington/Downtown
Hilton Lexington/Downtown
3.5 out of 5
369 West Vine Street, Lexington, KY
Stay at this 3.5-star business-friendly hotel in Lexington. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.4/10 Very Good! (1,004 reviews)
"Great"

Reviewed on Jul 7, 2025

Hilton Lexington/Downtown
Fairfield Inn & Suites by Marriott Lexington North
Fairfield Inn & Suites by Marriott Lexington North
3 out of 5
2100 Hackney Pl, Lexington, KY
Stay at this 3-star business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,003 reviews)
"Comfortable rooms and clean bathrooms. Complimentary breakfast and coffee was great. Parking space was good as well."

Reviewed on Jul 8, 2025

Fairfield Inn & Suites by Marriott Lexington North
GuestHouse Lexington
GuestHouse Lexington
2.5 out of 5
2261 Elkhorn Road, Lexington, KY
Book a stay at this business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8/10 Very Good! (1,241 reviews)
"We had a wonderful stay at your hotel ! Friendly staff , clean rooms and great amenities .. we will definitely be back ...."

Reviewed on Jul 5, 2025

GuestHouse Lexington
Embassy Suites by Hilton Lexington/UK Coldstream
Embassy Suites by Hilton Lexington/UK Coldstream
3.5 out of 5
1801 Newtown Pike, Lexington, KY
Stay at this 3.5-star business-friendly hotel in Lexington. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the ...
8.6/10 Excellent! (1,016 reviews)
Needs some upkeep. Pet friendly&good breakfast.
"We have stayed here numerous times over the years. The hotel is in need of some upkeep. We did appreciate the made to order breakfast and the pet friendly environment. Unfortunately they do charge for parking along with our visitors that came one evening and had to pay $20 just to visit us and have ..."

Reviewed on Jul 7, 2025

Embassy Suites by Hilton Lexington/UK Coldstream
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.