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Winchester

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Winchester Flights as Low as $46

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

Frontier Airlines
Tue, Jan 12 - Tue, Jan 19
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$46 Roundtrip, found 1 hour ago
$46
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Jan 12 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Jan 19, priced at $46 found 1 hour ago
Frontier Airlines
Wed, Dec 2 - Tue, Dec 15
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$56 Roundtrip, just found
$56
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Tue, Dec 15, priced at $56 just found
Frontier Airlines
Tue, Dec 1 - Tue, Dec 15
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$56 Roundtrip, found 1 hour ago
$56
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Dec 1 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Dec 15, priced at $56 found 1 hour ago
Frontier Airlines
Thu, Nov 12 - Sat, Nov 14
FLL
Fort Lauderdale - Hollywood Intl.
IAD
Washington Dulles Intl.
$78 Roundtrip, found 4 hours ago
$78
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Thu, Nov 12 from Fort Lauderdale - Hollywood Intl. to Washington Dulles Intl., returning Sat, Nov 14, priced at $78 found 4 hours ago
Frontier Airlines
Sat, Dec 5 - Sat, Dec 12
DFW
Dallas-Fort Worth Intl.
IAD
Washington Dulles Intl.
$83 Roundtrip, found 1 day ago
$83
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Dec 5 from Dallas-Fort Worth Intl. to Washington Dulles Intl., returning Sat, Dec 12, priced at $83 found 1 day ago
JetBlue Airways
Mon, Feb 1 - Sat, Feb 13
BOS
Logan Intl.
DCA
Ronald Reagan Washington National
$117 Roundtrip, found 1 hour ago
$117
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Mon, Feb 1 from Logan Intl. to Ronald Reagan Washington National, returning Sat, Feb 13, priced at $117 found 1 hour ago
Delta
Tue, Dec 8 - Tue, Dec 15
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$117 Roundtrip, found 1 hour ago
$117
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Dec 8 from Logan Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Dec 15, priced at $117 found 1 hour ago
Southwest Airlines
Tue, Dec 8 - Tue, Dec 15
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$117 Roundtrip, found 1 hour ago
$117
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Tue, Dec 8 from Logan Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Dec 15, priced at $117 found 1 hour ago
Frontier Airlines
Tue, Dec 15 - Wed, Dec 16
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$120 Roundtrip, just found
$120
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Dec 15 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Dec 16, priced at $120 just found
JetBlue Airways
Wed, Dec 2 - Tue, Dec 8
FLL
Fort Lauderdale - Hollywood Intl.
DCA
Ronald Reagan Washington National
$137 Roundtrip, just found
$137
Roundtrip
just found
Select JetBlue Airways flight, departing Wed, Dec 2 from Fort Lauderdale - Hollywood Intl. to Ronald Reagan Washington National, returning Tue, Dec 8, priced at $137 just found
Southwest Airlines
Tue, Jan 19 - Sat, Feb 6
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$137 Roundtrip, found 1 hour ago
$137
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Tue, Jan 19 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Sat, Feb 6, priced at $137 found 1 hour ago
Southwest Airlines
Tue, Dec 15 - Wed, Dec 16
DAL
Love Field
BWI
Baltimore Washington Intl. Thurgood Marshall
$209 Roundtrip, just found
$209
Roundtrip
just found
Select Southwest Airlines flight, departing Tue, Dec 15 from Love Field to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Dec 16, priced at $209 just found
Frontier Airlines
Tue, Jan 19 - Sat, Feb 6
DFW
Dallas-Fort Worth Intl.
DCA
Ronald Reagan Washington National
$210 Roundtrip, found 1 hour ago
$210
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Jan 19 from Dallas-Fort Worth Intl. to Ronald Reagan Washington National, returning Sat, Feb 6, priced at $210 found 1 hour ago
Frontier Airlines
Sat, Dec 12 - Sat, Dec 19
BOS
Logan Intl.
IAD
Washington Dulles Intl.
$210 Roundtrip, found 13 hours ago
$210
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Sat, Dec 12 from Logan Intl. to Washington Dulles Intl., returning Sat, Dec 19, priced at $210 found 13 hours ago
Southwest Airlines
Tue, Jan 19 - Sat, Feb 6
DAL
Love Field
DCA
Ronald Reagan Washington National
$309 Roundtrip, found 1 hour ago
$309
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Tue, Jan 19 from Love Field to Ronald Reagan Washington National, returning Sat, Feb 6, priced at $309 found 1 hour ago
Delta
Sat, Dec 5 - Sat, Dec 12
DAL
Love Field
IAD
Washington Dulles Intl.
$325 Roundtrip, found 1 day ago
$325
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Dec 5 from Love Field to Washington Dulles Intl., returning Sat, Dec 12, priced at $325 found 1 day 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 DCA 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 16 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 Washington Dulles Intl. 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 $46, 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 $46 right now, why wait?

Winchester Flight Information
Destination airport
Washington Dulles Intl.
Destination airport IATA code
IAD
Roundtrip price
$56

Last Minute Hotel Deals in Winchester

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike Winchester VA
Stay at this motel in Winchester. Enjoy free parking, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in ...
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Travelodge by Wyndham Winchester
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza Winchester VA
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and ...
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Microtel Inn & Suites by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3 out of 5
1055 Millwood Pike, Route 50 East Winchester VA
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (2,275 reviews)
"This was one of the worst stays I’ve had ! The facility did even come close to the rating given on line and we were very disappointed in our stay. Definitely won’t be staying in another La Quinta hotel anytime in the future. The bedding was poor and the room was minimal at best ! Not a very well ..."

Reviewed on Nov 10, 2026

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La Quinta Inn & Suites by Wyndham Winchester
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
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TRU By Hilton Winchester
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5
103 E Piccadilly St Winchester VA
Book a stay at this spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
9.4/10 Exceptional! (1,006 reviews)
"The property was clean, quiet and comfortable. We had a room not facing the street, others in our party were facing the street and it was noisy. The bar was great, as well as the staff. Will definitely try to go back."

Reviewed on Nov 7, 2026

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The George Washington Hotel, A Wyndham Grand Hotel
Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

2.5 out of 5
195 Kernstown Commons Blvd Winchester VA
Book a stay at this golf hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
9.4/10 Exceptional! (1,158 reviews)
"There was no one at the counter to check in. There was no soap by the tub and the breakfast was minimal. Pretty noisy from near highway."

Reviewed on Nov 10, 2026

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Comfort Inn & Suites Winchester
Quality Inn Winchester

Quality Inn Winchester

2.5 out of 5
1601 Martinsburg Pike Winchester VA
Stay at this hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
9.4/10 Exceptional! (1,007 reviews)
"Everything was great especially the price. And breakfast was great. Very pleased."

Reviewed on Nov 10, 2026

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Quality Inn Winchester
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

3 out of 5
141 Kernstown Commons Blvd Winchester VA
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
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Country Inn & Suites by Radisson, Winchester, VA
See all 2,198 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.