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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
$256

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! (629 reviews)
"Friendly and helpful staff. Rooms were nice and clean."

Reviewed on Sep 23, 2025

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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! (1,134 reviews)
"Great value for the money"

Reviewed on Sep 18, 2025

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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! (923 reviews)
"Clean and new property. Walking distance from fast food and a short drive from other restaurants. Close to the freeway exits."

Reviewed on Sep 22, 2025

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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! (279 reviews)
"Property is kind of off by itself next to other hotels, but this is preferable rather than be on top of the busy street considering this is an area where everything is easily in driving distance. Staff all were kind. Breakfast options were limited but always stocked and seemed fresh. Rooms clean ..."

Reviewed on Sep 19, 2025

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La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB
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! (775 reviews)
"Was very clean, staff were super friendly, highly recommend"

Reviewed on Sep 23, 2025

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Quality Inn Monteagle
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! (878 reviews)
"Great hotel with very friendly staff."

Reviewed on Sep 22, 2025

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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! (375 reviews)
"We had an absolutely fabulous stay here. We came just one night from Chattanooga for an anniversary dinner at High Point Restaurant (which is just about a 10 minute drive). The Inn is super clean and so comfortable. They do a turn down service and have bathrobes, the room even has an umbrella. We ..."

Reviewed on Aug 18, 2025

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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! (596 reviews)
Mostly good some fixable issues
"Customer service was good. Bed was comfortable. Only 3 sets of everything in a room for 4. Not a big deal, but seems like it’s an easy fix. There was dried boogers on the wall, paint ripped from the wall, and missed food trash on the floor from before. Cleaning could’ve been more of a priority."

Reviewed on Sep 21, 2025

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Best Western Shelbyville Inn and Suites Celebration Inn
See all 659 properties in Winchester
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.