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Winchester

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Winchester Flights as Low as $133

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Delta
Tue, Sep 8 - Sat, Sep 12
ATL
Hartsfield-Jackson Atlanta Intl.
BNA
Nashville Intl.
$133 Roundtrip, found 1 hour ago
$133
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Sep 8 from Hartsfield-Jackson Atlanta Intl. to Nashville Intl., returning Sat, Sep 12, priced at $133 found 1 hour ago
JetBlue Airways
Mon, Sep 14 - Sat, Sep 19
JFK
John F. Kennedy Intl.
BNA
Nashville Intl.
$147 Roundtrip, just found
$147
Roundtrip
just found
Select JetBlue Airways flight, departing Mon, Sep 14 from John F. Kennedy Intl. to Nashville Intl., returning Sat, Sep 19, priced at $147 just found
United
Tue, Sep 22 - Sat, Sep 26
EWR
Newark Liberty Intl. Airport
BNA
Nashville Intl.
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select United flight, departing Tue, Sep 22 from Newark Liberty Intl. Airport to Nashville Intl., returning Sat, Sep 26, priced at $157 found 1 day ago
Frontier Airlines
Mon, Aug 24 - Thu, Aug 27
DFW
Dallas-Fort Worth Intl.
BNA
Nashville Intl.
$172 Roundtrip, found 1 hour ago
$172
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Mon, Aug 24 from Dallas-Fort Worth Intl. to Nashville Intl., returning Thu, Aug 27, priced at $172 found 1 hour ago
Bargain Flight
Wed, Dec 2 - Mon, Dec 7
MSP
Minneapolis - St. Paul Intl.
BNA
Nashville Intl.
$219 Roundtrip, found 3 days ago
$219
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Wed, Dec 2 from Minneapolis - St. Paul Intl. to Nashville Intl., returning Mon, Dec 7, priced at $219 found 3 days ago
United
Fri, Aug 21 - Wed, Sep 9
EWR
Newark Liberty Intl. Airport
CHA
Chattanooga Metropolitan
$245 Roundtrip, found 18 hours ago
$245
Roundtrip
found 18 hours ago
Select United flight, departing Fri, Aug 21 from Newark Liberty Intl. Airport to Chattanooga Metropolitan, returning Wed, Sep 9, priced at $245 found 18 hours ago
Bargain Flight
Wed, Sep 30 - Fri, Oct 2
PHX
Sky Harbor Intl.
BNA
Nashville Intl.
$259 Roundtrip, found 1 day ago
$259
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Wed, Sep 30 from Sky Harbor Intl. to Nashville Intl., returning Fri, Oct 2, priced at $259 found 1 day ago
Delta
Tue, Aug 25 - Thu, Aug 27
DAL
Love Field
BNA
Nashville Intl.
$277 Roundtrip, found 1 hour ago
$277
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Aug 25 from Love Field to Nashville Intl., returning Thu, Aug 27, priced at $277 found 1 hour ago
Delta
Wed, Aug 26 - Tue, Sep 15
EWR
Newark Liberty Intl. Airport
HSV
Huntsville Intl.
$281 Roundtrip, found 1 day ago
$281
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Aug 26 from Newark Liberty Intl. Airport to Huntsville Intl., returning Tue, Sep 15, priced at $281 found 1 day ago
Bargain Flight
Wed, Aug 12 - Sat, Aug 22
PHX
Sky Harbor Intl.
HSV
Huntsville Intl.
$294 Roundtrip, found 1 day ago
$294
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Wed, Aug 12 from Sky Harbor Intl. to Huntsville Intl., returning Sat, Aug 22, priced at $294 found 1 day ago
Bargain Flight
Thu, Aug 13 - Mon, Aug 17
DFW
Dallas-Fort Worth Intl.
HSV
Huntsville Intl.
$310 Roundtrip, found 1 day ago
$310
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Thu, Aug 13 from Dallas-Fort Worth Intl. to Huntsville Intl., returning Mon, Aug 17, priced at $310 found 1 day ago
Delta
Wed, Jul 15 - Tue, Jul 21
MSP
Minneapolis - St. Paul Intl.
CHA
Chattanooga Metropolitan
$339 Roundtrip, found 1 day ago
$339
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jul 15 from Minneapolis - St. Paul Intl. to Chattanooga Metropolitan, returning Tue, Jul 21, priced at $339 found 1 day ago
American Airlines
Wed, Jul 1 - Sat, Jul 4
JFK
John F. Kennedy Intl.
HSV
Huntsville Intl.
$357 Roundtrip, found 1 day ago
$357
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Jul 1 from John F. Kennedy Intl. to Huntsville Intl., returning Sat, Jul 4, priced at $357 found 1 day ago
American Airlines
Sat, Oct 24 - Tue, Oct 27
JFK
John F. Kennedy Intl.
CHA
Chattanooga Metropolitan
$361 Roundtrip, found 5 days ago
$361
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Oct 24 from John F. Kennedy Intl. to Chattanooga Metropolitan, returning Tue, Oct 27, priced at $361 found 5 days ago
Delta
Wed, Aug 12 - Tue, Aug 18
DAL
Love Field
HSV
Huntsville Intl.
$525 Roundtrip, found 5 days ago
$525
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Aug 12 from Love Field to Huntsville Intl., returning Tue, Aug 18, priced at $525 found 5 days ago
Delta
Wed, Jul 1 - Sat, Jul 4
DFW
Dallas-Fort Worth Intl.
CHA
Chattanooga Metropolitan
$527 Roundtrip, found 3 days ago
$527
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Jul 1 from Dallas-Fort Worth Intl. to Chattanooga Metropolitan, returning Sat, Jul 4, priced at $527 found 3 days ago

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 September, 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 12 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 $133, 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 $133 right now, why wait?

Winchester Flight Information
Destination airport
Nashville Intl.
Destination airport IATA code
BNA
Roundtrip price
$181

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 ...
8.8/10 Excellent! (718 reviews)
"Fine for what it was. Room was very humid and musty. Check in was easy and staff was nice. Breakfast was basic but ok."

Reviewed on Jun 23, 2026

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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 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 ...
8.6/10 Excellent! (1,208 reviews)
"This place was really cute and the staff friendly and helpful. The only reason I'm giving it 4 starts instead of 5 is because the internet leaves a lot to be desired, and it's located in an area that doesn't get very good cell coverage so internet is kind of important. It went out frequently, but ..."

Reviewed on Jun 26, 2026

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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 ...
8.8/10 Excellent! (1,105 reviews)
"Great staff"

Reviewed on Jun 26, 2026

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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 ...
9.8/10 Exceptional! (440 reviews)
"Lovely hotel! Rooms are immaculate and property is gorgeous! Thank you for a wonderful Overnight stay!"

Reviewed on Jun 25, 2026

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The Sewanee Inn
Quality Inn Monteagle

Quality Inn Monteagle

2.5 out of 5
509 W Main St Monteagle TN
Stay at this hotel in Monteagle. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (889 reviews)
"The front desk person was very nice. The room in the hotel seemed to be clean. However, the room had a very strong smell when you walked in and it smelt like urine. I don’t know where the smell was coming from but it was strong. It’s a decent hotel. It’s just older and you can see they keep it clean, ..."

Reviewed on Jun 20, 2026

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Quality Inn Monteagle
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 hotel in Manchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (434 reviews)
"Nice hotel. Friendly staff. Hot breakfast. Hotel was updated and rooms were very clean. I would stay again."

Reviewed on Jun 27, 2026

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La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB
Lx Hotel, SureStay Collection by Best Western

Lx Hotel, SureStay Collection by Best Western

2.5 out of 5
201 Murfreesboro Highway Manchester TN
Book a stay at this business-friendly motel in Manchester. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff and the ...
9.6/10 Exceptional! (467 reviews)
"Excellent staff and good breakfast. It was great chatting with the owners who are great conversationalists so received an overall sense of genuine reception. Alex was kind enough to offer us the long drive to the airport late night when our taxi service canceled (fortunately Uber worked)."

Reviewed on Jun 27, 2026

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Lx Hotel, SureStay Collection by Best Western
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! (685 reviews)
"Over charged me, they didn’t have the reservation correct. So they charge me a second time causing me to show three rooms instead of the two we had booked."

Reviewed on Jun 26, 2026

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Holiday Inn Express Hotel & Suites Tullahoma by IHG
See all 751 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.