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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 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 , 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 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 , 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
Nashville Intl.
Destination airport IATA code
BNA
Roundtrip price
$312

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! (643 reviews)
"The room itself wasn’t bad and the beds are comfortable but the bathroom is disgusting. There are bugs in the shower, some are alive and some are dead. The fan that automatically comes on when you turn the bathroom light on is ridiculously loud and the lighting in the bathroom is so bad that it will ..."

Reviewed on Oct 10, 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 3-star hotel in Monteagle. Enjoy free parking, private pools, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (1,141 reviews)
"Easy access for wheelchair"

Reviewed on Oct 17, 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! (943 reviews)
"Best Microtel we have stayed at. Clean room, comfy beds, nice breakfast, friendly staff and soft towels."

Reviewed on Oct 15, 2025

Microtel Inn & Suites by Wyndham Manchester
La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB

La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB

3 out of 5
120 Hospitality Blvd, Manchester, TN
Stay at this 3-star hotel in Manchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.6/10 Excellent! (287 reviews)
"Was a quick overnight stay, suited my needs"

Reviewed on Oct 15, 2025

La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB
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! (886 reviews)
"Fast check in and check out. Clean room. Comfy beds."

Reviewed on Oct 18, 2025

Comfort Suites Manchester near Arnold AFB
The Sewanee Inn

The Sewanee Inn

4 out of 5
1235 University Ave, Sewanee, TN
Stay at this 4-star 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! (379 reviews)
"This hotel is nice! It was nice that the rooms are on one side and the restaurant is on the other. Beautiful lobby and entryway. There was a fire going in the lobby when we arrived which made it feel cozy. The beds were soft which made for a great nights sleep! We definitely would stay here again! ..."

Reviewed on Oct 5, 2025

The Sewanee Inn
Best Western Shelbyville Inn and Suites Celebration Inn

Best Western Shelbyville Inn and Suites Celebration Inn

2.5 out of 5
724 Madison Street, Shelbyville, TN
Book a stay at this business-friendly hotel in Shelbyville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
7.8/10 Good! (605 reviews)
"The room was very clean and the breakfast was great."

Reviewed on Oct 15, 2025

Best Western Shelbyville Inn and Suites Celebration Inn
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! (1,003 reviews)
"The location was excellent for my needs and the facilities were clean."

Reviewed on Oct 17, 2025

Spark by Hilton Kimball
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.