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Winchester

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Winchester Flights as Low as $66

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

Frontier Airlines
Wed, Apr 22 - Sat, Apr 25
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$66 Roundtrip, found 3 hours ago
$66
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Wed, Apr 22 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Apr 25, priced at $66 found 3 hours ago
Frontier Airlines
Sat, May 9 - Sat, May 16
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$69 Roundtrip, just found
$69
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, May 9 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Sat, May 16, priced at $69 just found
Frontier Airlines
Mon, Mar 30 - Mon, Apr 6
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$78 Roundtrip, just found
$78
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Mar 30 from Orlando Intl. to Washington Dulles Intl., returning Mon, Apr 6, priced at $78 just found
Frontier Airlines
Sun, Aug 16 - Mon, Sep 7
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$97 Roundtrip, found 3 days ago
$97
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sun, Aug 16 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Sep 7, priced at $97 found 3 days ago
Breeze Airways
Fri, Mar 27 - Mon, Apr 6
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$121 Roundtrip, found 1 day ago
$121
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Mar 27 from Orlando Intl. to Washington Dulles Intl., returning Mon, Apr 6, priced at $121 found 1 day ago
JetBlue Airways
Sat, May 9 - Mon, May 11
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$144 Roundtrip, found 5 days ago
$144
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sat, May 9 from Orlando Intl. to Ronald Reagan Washington National, returning Mon, May 11, priced at $144 found 5 days ago
Frontier Airlines
Wed, Apr 22 - Tue, May 5
LAX
Los Angeles Intl.
DCA
Ronald Reagan Washington National
$160 Roundtrip, found 3 days ago
$160
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Apr 22 from Los Angeles Intl. to Ronald Reagan Washington National, returning Tue, May 5, priced at $160 found 3 days ago
Frontier Airlines
Wed, Apr 22 - Tue, May 5
LAX
Los Angeles Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$160 Roundtrip, found 17 hours ago
$160
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Wed, Apr 22 from Los Angeles Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, May 5, priced at $160 found 17 hours ago
Delta
Tue, May 12 - Tue, May 26
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$179 Roundtrip, found 6 days ago
$179
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, May 12 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Tue, May 26, priced at $179 found 6 days ago
Frontier Airlines
Wed, Apr 22 - Sat, May 9
LAX
Los Angeles Intl.
IAD
Washington Dulles Intl.
$220 Roundtrip, found 2 days ago
$220
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Apr 22 from Los Angeles Intl. to Washington Dulles Intl., returning Sat, May 9, priced at $220 found 2 days ago
Frontier Airlines
Sat, Apr 18 - Fri, Apr 24
ONT
Los Angeles - Ontario Intl.
DCA
Ronald Reagan Washington National
$235 Roundtrip, found 6 days ago
$235
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Apr 18 from Los Angeles - Ontario Intl. to Ronald Reagan Washington National, returning Fri, Apr 24, priced at $235 found 6 days ago
Frontier Airlines
Fri, Apr 17 - Thu, May 7
ONT
Los Angeles - Ontario Intl.
IAD
Washington Dulles Intl.
$244 Roundtrip, found 1 day ago
$244
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Apr 17 from Los Angeles - Ontario Intl. to Washington Dulles Intl., returning Thu, May 7, priced at $244 found 1 day ago
Frontier Airlines
Sat, Apr 4 - Thu, Apr 9
ONT
Los Angeles - Ontario Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$282 Roundtrip, found 2 days ago
$282
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Apr 4 from Los Angeles - Ontario Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, Apr 9, priced at $282 found 2 days ago
Copa
Mon, May 11 - Thu, May 28
EZE
Ministro Pistarini Intl.
IAD
Washington Dulles Intl.
$777 Roundtrip, found 5 hours ago
$777
Roundtrip
found 5 hours ago
Select Copa flight, departing Mon, May 11 from Ministro Pistarini Intl. to Washington Dulles Intl., returning Thu, May 28, priced at $777 found 5 hours ago
Copa
Tue, Jun 2 - Sun, Jun 14
EZE
Ministro Pistarini Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$801 Roundtrip, found 5 hours ago
$801
Roundtrip
found 5 hours ago
Select Copa flight, departing Tue, Jun 2 from Ministro Pistarini Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Jun 14, priced at $801 found 5 hours ago
Delta
Tue, Jun 2 - Wed, Jun 17
EZE
Ministro Pistarini Intl.
DCA
Ronald Reagan Washington National
$813 Roundtrip, found 5 hours ago
$813
Roundtrip
found 5 hours ago
Select Delta flight, departing Tue, Jun 2 from Ministro Pistarini Intl. to Ronald Reagan Washington National, returning Wed, Jun 17, priced at $813 found 5 hours 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 April, 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 Eastern West Virginia Regional 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 $66, 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 $66 right now, why wait?

Winchester Flight Information
Destination airport
Washington Dulles Intl.
Destination airport IATA code
IAD
Roundtrip price
$77

Last Minute Hotel Deals in Winchester

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

3 out of 5
333 Front Royal Pike Winchester VA
Book a stay at this business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
9/10 Wonderful! (1,003 reviews)
Very clean, nice bar/restaurant, convenient location. Excellent breakfast! Will definitely stay again when traveling 😄

Reviewed on Mar 14, 2026

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Holiday Inn Winchester Se-Historic Gateway by IHG
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! (2,281 reviews)
Fairly clean and reasonably spacious. Nothing special, but a perfectly fine option for a short one-night stay.

Reviewed on Mar 16, 2026

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La Quinta Inn & Suites by Wyndham 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! (1,008 reviews)
Very nice and conveniently located

Reviewed on Mar 16, 2026

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The George Washington Hotel, A Wyndham Grand Hotel
Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University

2.5 out of 5
140 Costello Dr 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 ...
7.8/10 Good! (1,005 reviews)
Yes the kitchen was a blessing

Reviewed on Mar 16, 2026

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Sleep Inn & Suites Winchester near University
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 WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,441 reviews)
Staff were very nice. Clean room and diningroom. Easy on & off Rt 81. in Winchester. 1 1/2 hr to the car train in Lorton Va. Great way to eliminate crazy traffic on Rt 95 to go Rt66 off Rt 81.

Reviewed on Mar 16, 2026

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Microtel Inn & Suites by Wyndham Winchester
Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

3 out of 5
300 Marriott Drive Winchester VA
Book a stay at this business-friendly hotel in Winchester. Enjoy free parking, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
9/10 Wonderful! (943 reviews)
Great location

Reviewed on Mar 15, 2026

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Courtyard by Marriott Winchester
SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

2.5 out of 5
280 MARKET STREET 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 ...
9.4/10 Exceptional! (821 reviews)
SpringHill Suites is my go-to hotel in the Winchester area.

Reviewed on Mar 16, 2026

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SpringHill Suites by Marriott Winchester
Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area

2.5 out of 5
640 East Jubal Early Drive 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 and the clean ...
9/10 Wonderful! (1,002 reviews)
Nice lobby, nice room, ample parking, good breakfast selection, good area around the hotel

Reviewed on Mar 15, 2026

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Hampton Inn Winchester-University/Mall Area
See all 2,045 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.