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Winchester

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Winchester Flights as Low as $79

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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 CHA 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 January, 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 15 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 Chattanooga Metropolitan 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 $79, 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 $79 right now, why wait?

Winchester Flight Information
Destination airport
Nashville Intl.
Destination airport IATA code
BNA
Roundtrip price
$104

Last Minute Hotel Deals in Winchester

Best Western Inn

Best Western Inn

2.5 out of 5
1602 Dinah Shore Boulevard Winchester TN
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the helpful staff and the ...
8.6/10 Excellent! (663 reviews)
Clean room. Quiet - no fans unkess I turned it on. Convenient parking and ice close to rokm.

Reviewed on Dec 18, 2025

Best Western Inn
The Smokehouse Lodge and Cabins

The Smokehouse Lodge and Cabins

3 out of 5
844 W Main Street Monteagle TN
Stay at this hotel in Monteagle. Enjoy free parking, private pools, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
8.4/10 Very Good! (1,143 reviews)
Great

Reviewed on Dec 23, 2025

The Smokehouse Lodge and Cabins
Microtel Inn & Suites by Wyndham Manchester

Microtel Inn & Suites by Wyndham Manchester

2 out of 5
201 Expressway Dr Manchester TN
Book a stay at this business-friendly hotel in Manchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (1,006 reviews)
It was Great

Reviewed on Dec 24, 2025

Microtel Inn & Suites by Wyndham Manchester
The Sewanee Inn

The Sewanee Inn

4 out of 5
1235 University Ave Sewanee TN
Book a stay at this golf hotel in Sewanee. Enjoy free WiFi, a golf course, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
9.6/10 Exceptional! (392 reviews)
Breakfast is tomorrow

Reviewed on Dec 19, 2025

The Sewanee Inn
Comfort Suites Manchester near Arnold AFB

Comfort Suites Manchester near Arnold AFB

2.5 out of 5
152 Hospitality Blvd Manchester TN
Book a stay at this business-friendly hotel in Manchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (935 reviews)
Room smelled a bit like a dog and the shower only ever got to lukewarm at the warmest.

Reviewed on Dec 21, 2025

Comfort Suites Manchester near Arnold AFB
Spark by Hilton Kimball

Spark by Hilton Kimball

2.5 out of 5
205 Kimball Crossing Dr Jasper TN
Stay at this hotel in Jasper. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8.2/10 Very Good! (1,004 reviews)
Yes

Reviewed on Dec 23, 2025

Spark by Hilton Kimball
LivSmart Studios by Hilton Tullahoma

LivSmart Studios by Hilton Tullahoma

2.5 out of 5
251 William Northern Blvd. Tullahoma TN
Book a stay at this business-friendly hotel in Tullahoma. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Northgate Mall Tullahoma and ...
9.4/10 Exceptional! (21 reviews)
Clean room!! Great staff

Reviewed on Dec 22, 2025

LivSmart Studios by Hilton Tullahoma
Quality Inn Monteagle

Quality Inn Monteagle

2.5 out of 5
509 W Main St Pelham TN
Stay at this hotel in Pelham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8.6/10 Excellent! (820 reviews)
Clean room and quiet stay. Breakfast was good as well.

Reviewed on Dec 15, 2025

Quality Inn Monteagle
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.