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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
Winchester
Destination airport IATA code
CHA

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! (650 reviews)
very good

Reviewed on Nov 3, 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! (1,132 reviews)
Clean room, parking convenient bed comfortable, staff friendly.

Reviewed on Nov 9, 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! (969 reviews)
Great staff and a perfectly adequate room. Loads of food options nearby

Reviewed on Nov 11, 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! (303 reviews)
The room was nice and clean, the staff was very nice and helpful. Hotel nice and clean as well.

Reviewed on Nov 9, 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! (910 reviews)
Clean and comfortable. Great customer service.

Reviewed on Nov 10, 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! (1,002 reviews)
Nice staff, clean room, breakfast with limited sitting and options if you come at popular hours

Reviewed on Nov 9, 2025

Spark by Hilton Kimball
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! (383 reviews)
We just stayed one night. We wanted to play the adjacent 9 hole golf course (excellent as well). Was not expecting this at all. No exaggeration but we’ve stayed in hotels/rooms that cost 10 times as much and were no nicer. Will absolutely stay here again.

Reviewed on Oct 28, 2025

The Sewanee Inn
Holiday Inn Express Hotel & Suites Tullahoma by IHG

Holiday Inn Express Hotel & Suites Tullahoma by IHG

2.5 out of 5
2030 N Jackson Street, Tullahoma, TN
Book a stay at this business-friendly hotel in Tullahoma. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.8/10 Excellent! (627 reviews)
Yes

Reviewed on Nov 11, 2025

Holiday Inn Express Hotel & Suites Tullahoma by IHG
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.