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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 2 hours ago
$66
Roundtrip
found 2 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 2 hours ago
Frontier Airlines
Sat, May 9 - Sat, May 16
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$69 Roundtrip, found 2 hours ago
$69
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sat, May 9 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Sat, May 16, priced at $69 found 2 hours ago
Frontier Airlines
Sat, Apr 25 - Sat, May 9
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$88 Roundtrip, found 2 hours ago
$88
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sat, Apr 25 from Orlando Intl. to Washington Dulles Intl., returning Sat, May 9, priced at $88 found 2 hours ago
Frontier Airlines
Wed, Aug 19 - Mon, Sep 7
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$88 Roundtrip, found 17 hours ago
$88
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Wed, Aug 19 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Sep 7, priced at $88 found 17 hours ago
Breeze Airways
Mon, Mar 30 - Mon, Apr 6
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$110 Roundtrip, found 4 days ago
$110
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Mon, Mar 30 from Orlando Intl. to Washington Dulles Intl., returning Mon, Apr 6, priced at $110 found 4 days ago
JetBlue Airways
Wed, Apr 8 - Tue, Apr 14
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$142 Roundtrip, found 4 days ago
$142
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Wed, Apr 8 from Orlando Intl. to Ronald Reagan Washington National, returning Tue, Apr 14, priced at $142 found 4 days ago
Frontier Airlines
Wed, Apr 22 - Tue, May 5
LAX
Los Angeles Intl.
DCA
Ronald Reagan Washington National
$160 Roundtrip, found 2 days ago
$160
Roundtrip
found 2 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 2 days ago
Frontier Airlines
Wed, Apr 22 - Tue, May 5
LAX
Los Angeles Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$160 Roundtrip, just found
$160
Roundtrip
just found
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 just found
American Airlines
Wed, Apr 22 - Sat, May 9
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$177 Roundtrip, found 20 hours ago
$177
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Wed, Apr 22 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Sat, May 9, priced at $177 found 20 hours ago
Spirit Airlines
Thu, Mar 26 - Tue, Apr 7
AUS
Austin-Bergstrom Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$196 Roundtrip, found 21 hours ago
$196
Roundtrip
found 21 hours ago
Select Spirit Airlines flight, departing Thu, Mar 26 from Austin-Bergstrom Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Apr 7, priced at $196 found 21 hours ago
Frontier Airlines
Wed, Apr 22 - Sat, May 9
LAX
Los Angeles Intl.
IAD
Washington Dulles Intl.
$220 Roundtrip, found 1 day ago
$220
Roundtrip
found 1 day 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 1 day ago
Frontier Airlines
Thu, Apr 16 - Sat, May 2
AUS
Austin-Bergstrom Intl.
IAD
Washington Dulles Intl.
$220 Roundtrip, found 5 days ago
$220
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Apr 16 from Austin-Bergstrom Intl. to Washington Dulles Intl., returning Sat, May 2, priced at $220 found 5 days ago
Frontier Airlines
Tue, Apr 14 - Thu, May 7
AUS
Austin-Bergstrom Intl.
DCA
Ronald Reagan Washington National
$225 Roundtrip, found 5 days ago
$225
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Apr 14 from Austin-Bergstrom Intl. to Ronald Reagan Washington National, returning Thu, May 7, priced at $225 found 5 days ago
Delta
Tue, Jun 2 - Wed, Jun 17
EZE
Ministro Pistarini Intl.
DCA
Ronald Reagan Washington National
$813 Roundtrip, found 9 hours ago
$813
Roundtrip
found 9 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 9 hours ago
Delta
Mon, May 11 - Sun, Jun 14
EZE
Ministro Pistarini Intl.
IAD
Washington Dulles Intl.
$813 Roundtrip, found 16 hours ago
$813
Roundtrip
found 16 hours ago
Select Delta flight, departing Mon, May 11 from Ministro Pistarini Intl. to Washington Dulles Intl., returning Sun, Jun 14, priced at $813 found 16 hours ago
Delta
Tue, Jun 2 - Sun, Jun 14
EZE
Ministro Pistarini Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$813 Roundtrip, found 9 hours ago
$813
Roundtrip
found 9 hours ago
Select Delta flight, departing Tue, Jun 2 from Ministro Pistarini Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Jun 14, priced at $813 found 9 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
Baltimore Washington Intl. Thurgood Marshall
Destination airport IATA code
BWI
Roundtrip price
$66

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! (2,280 reviews)
Not your average hotel. Unique room layout, modern lobby and friendly staff!

Reviewed on Mar 15, 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! (1,007 reviews)
Great stay!

Reviewed on Mar 15, 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! (1,004 reviews)
This is the dirtiest hotel I’ve ever stayed at. There was an earwig in the bathroom. The bed cover was dirty, everything was dingy. The walls, the chair. The one side of the mattress springs were so wore and broken. The plug in the bathroom didn’t work. The handicap bar was out of the wall. You can ...

Reviewed on Mar 15, 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! (1,440 reviews)
Clean rooms.

Reviewed on Mar 7, 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! (820 reviews)
Have stayed at a SpringHill Suites several times at various locations and I am never disappointed. Always clean, always comfortable, and the staff is always pleasant

Reviewed on Mar 15, 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 2,047 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.