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Winchester

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Winchester Flights as Low as $58

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

Frontier Airlines
Tue, Jun 30 - Wed, Jul 1
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$58 Roundtrip, found 20 hours ago
$58
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Tue, Jun 30 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Wed, Jul 1, priced at $58 found 20 hours ago
Frontier Airlines
Tue, Jun 30 - Tue, Jun 30
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$58 Roundtrip, found 1 day ago
$58
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Jun 30 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Jun 30, priced at $58 found 1 day ago
Frontier Airlines
Wed, Jul 1 - Wed, Jul 8
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$66 Roundtrip, found 1 day ago
$66
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Jul 1 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Jul 8, priced at $66 found 1 day ago
Frontier Airlines
Wed, Aug 5 - Tue, Aug 25
FLL
Fort Lauderdale - Hollywood Intl.
IAD
Washington Dulles Intl.
$86 Roundtrip, found 3 days ago
$86
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Aug 5 from Fort Lauderdale - Hollywood Intl. to Washington Dulles Intl., returning Tue, Aug 25, priced at $86 found 3 days ago
Frontier Airlines
Wed, Sep 2 - Tue, Sep 8
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$98 Roundtrip, found 3 hours ago
$98
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Wed, Sep 2 from Orlando Intl. to Washington Dulles Intl., returning Tue, Sep 8, priced at $98 found 3 hours ago
Frontier Airlines
Wed, Aug 12 - Wed, Sep 2
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$98 Roundtrip, found 1 day ago
$98
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Aug 12 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Sep 2, priced at $98 found 1 day ago
United
Tue, Jun 30 - Wed, Jul 1
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$181 Roundtrip, found 20 hours ago
$181
Roundtrip
found 20 hours ago
Select United flight, departing Tue, Jun 30 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Wed, Jul 1, priced at $181 found 20 hours ago
Bargain Flight
Wed, Aug 12 - Wed, Aug 26
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$184 Roundtrip, found 2 days ago
$184
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Wed, Aug 12 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Wed, Aug 26, priced at $184 found 2 days ago
American Airlines
Tue, Jul 21 - Tue, Aug 4
FLL
Fort Lauderdale - Hollywood Intl.
DCA
Ronald Reagan Washington National
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jul 21 from Fort Lauderdale - Hollywood Intl. to Ronald Reagan Washington National, returning Tue, Aug 4, priced at $197 found 1 day ago
Frontier Airlines
Thu, Jun 18 - Mon, Jun 22
IAH
George Bush Intercontinental
IAD
Washington Dulles Intl.
$215 Roundtrip, found 6 days ago
$215
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Jun 18 from George Bush Intercontinental to Washington Dulles Intl., returning Mon, Jun 22, priced at $215 found 6 days ago
Bargain Flight
Wed, Jul 15 - Tue, Jul 21
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$222 Roundtrip, found 1 day ago
$222
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Wed, Jul 15 from Orlando Intl. to Ronald Reagan Washington National, returning Tue, Jul 21, priced at $222 found 1 day ago
Frontier Airlines
Sat, Sep 26 - Tue, Sep 29
IAH
George Bush Intercontinental
BWI
Baltimore Washington Intl. Thurgood Marshall
$244 Roundtrip, found 6 days ago
$244
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Sep 26 from George Bush Intercontinental to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Sep 29, priced at $244 found 6 days ago
Delta
Sat, Aug 29 - Tue, Sep 15
LAX
Los Angeles Intl.
DCA
Ronald Reagan Washington National
$263 Roundtrip, found 5 days ago
$263
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Aug 29 from Los Angeles Intl. to Ronald Reagan Washington National, returning Tue, Sep 15, priced at $263 found 5 days ago
United
Wed, Aug 12 - Sat, Aug 29
LAX
Los Angeles Intl.
IAD
Washington Dulles Intl.
$266 Roundtrip, found 2 days ago
$266
Roundtrip
found 2 days ago
Select United flight, departing Wed, Aug 12 from Los Angeles Intl. to Washington Dulles Intl., returning Sat, Aug 29, priced at $266 found 2 days ago
Bargain Flight
Thu, Sep 10 - Sat, Sep 19
LAX
Los Angeles Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$280 Roundtrip, found 6 days ago
$280
Roundtrip
found 6 days ago
Select Bargain Flight flight, departing Thu, Sep 10 from Los Angeles Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Sep 19, priced at $280 found 6 days ago
Frontier Airlines
Mon, Jul 27 - Mon, Aug 17
IAH
George Bush Intercontinental
DCA
Ronald Reagan Washington National
$294 Roundtrip, found 4 days ago
$294
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Mon, Jul 27 from George Bush Intercontinental to Ronald Reagan Washington National, returning Mon, Aug 17, priced at $294 found 4 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 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 June, 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 13 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 $58, 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 $58 right now, why wait?

Winchester Flight Information
Destination airport
Washington Dulles Intl.
Destination airport IATA code
IAD
Roundtrip price
$57

Last Minute Hotel Deals in Winchester

Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr 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 ...
9/10 Wonderful! (1,002 reviews)
"Staff were on top of everything, very roomy rooms, clean, and the hotel it self was clean. The morning meals was basic but plenty and fresh."

Reviewed on May 18, 2026

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Spark by Hilton 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. ...
9/10 Wonderful! (871 reviews)
"Room very clean .. great to play pool .. but at breakfast had to ask for more oatmeal as it was empty even though the woman was standing right there. She was not paying attention to what was needed"

Reviewed on May 20, 2026

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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! (1,000 reviews)
"You can’t go wrong staying here. The staff were very friendly. The beds were very comfortable and the room was very clean. This hotel is centrally located so you can park your car and walk around the old town area. This was our second time staying here and it didn’t disappoint. We will definitely ..."

Reviewed on May 17, 2026

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The George Washington Hotel, A Wyndham Grand Hotel
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! (1,467 reviews)
"Breakfast bar was wonderful. The staff was friendly. The room was great and kept clean and the bed was comfortable. Highly recommend them and i will definitely will stay again."

Reviewed on May 19, 2026

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Microtel Inn & Suites by Wyndham 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 WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.6/10 Excellent! (1,076 reviews)
"Very nice convenient and friendly. Highly recommend"

Reviewed on May 19, 2026

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Travelodge by Wyndham 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! (1,001 reviews)
"Had trouble checking in. The lady could not find our reservation. Took some time for her to find it. Right now checking on why were charged more than what we were to be charged."

Reviewed on May 20, 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 ...
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La Quinta 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! (979 reviews)
"More lighting in room (especially bathroom) would be a plus."

Reviewed on May 17, 2026

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Courtyard by Marriott Winchester
See all 2,040 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.