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Winchester

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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 , 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 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 , 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
LEX

Last Minute Hotel Deals in Winchester

Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 out of 5
1307 W Lexington Ave, Winchester, KY
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (972 reviews)
"Super clean!! Great breakfast"

Reviewed on Sep 11, 2025

Best Western Winchester Hotel
GLō Best Western Lexington

GLō Best Western Lexington

3 out of 5
1935 Stanton Way, Lexington, KY
Stay at this 3-star hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular ...
9.2/10 Wonderful! (2,260 reviews)
"Love the place"

Reviewed on Sep 19, 2025

GLō Best Western Lexington
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! (1,009 reviews)
"The room was immaculate."

Reviewed on Sep 22, 2025

Hilton Lexington/Downtown
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 ...
8.2/10 Very Good! (1,379 reviews)
"We loved our stay at thos property. The staff was very friendly and the hotel was very clean."

Reviewed on Sep 21, 2025

GuestHouse Lexington
Hyatt Regency Lexington

Hyatt Regency Lexington

3.5 out of 5
401 W High St, Lexington, KY
Stay at this 3.5-star business-friendly hotel in Lexington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.6/10 Excellent! (1,002 reviews)
"Great location"

Reviewed on Sep 14, 2025

Hyatt Regency 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! (1,021 reviews)
"We have stayed in this Hilton 3 times over the last many years. The last time was when we brought my mom back to Kentucky for her final time. We have also stayed in Hilton Suites in other states. We have stayed in many other hotels in many states. The Hilton in Lexington is the only place that charges ..."

Reviewed on Sep 21, 2025

Embassy Suites by Hilton Lexington/UK Coldstream
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 ...
8.6/10 Excellent! (155 reviews)
"Restful"

Reviewed on Sep 22, 2025

Spark by Hilton Lexington Hamburg
Motel 6 Lexington, KY - Airport

Motel 6 Lexington, KY - Airport

2 out of 5
750 Newtown Court, Lexington, KY
Stay at this motel in Lexington. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
5.8/10 (1,010 reviews)
"Great staff at desk"

Reviewed on Sep 17, 2025

Motel 6 Lexington, KY - Airport
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.