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Winchester

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Winchester Flights as Low as $56

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.
$56 Roundtrip, found 1 hour ago
$56
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Jun 30 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Wed, Jul 1, priced at $56 found 1 hour ago
Frontier Airlines
Sat, Jun 6 - Tue, Jun 9
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$56 Roundtrip, found 4 hours ago
$56
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, Jun 6 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Jun 9, priced at $56 found 4 hours ago
Spirit Airlines
Sat, Jun 6 - Tue, Jun 9
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$137 Roundtrip, found 4 hours ago
$137
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Sat, Jun 6 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Jun 9, priced at $137 found 4 hours ago
American Airlines
Wed, May 20 - Sun, May 24
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$164 Roundtrip, found 1 day ago
$164
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, May 20 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Sun, May 24, priced at $164 found 1 day ago
United
Tue, Jun 30 - Wed, Jul 1
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$169 Roundtrip, found 1 hour ago
$169
Roundtrip
found 1 hour ago
Select United flight, departing Tue, Jun 30 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Wed, Jul 1, priced at $169 found 1 hour ago
Delta
Wed, May 20 - Tue, May 26
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$173 Roundtrip, found 5 hours ago
$173
Roundtrip
found 5 hours ago
Select Delta flight, departing Wed, May 20 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Tue, May 26, priced at $173 found 5 hours ago
American Airlines
Wed, May 20 - Wed, May 27
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$173 Roundtrip, found 11 hours ago
$173
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Wed, May 20 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Wed, May 27, priced at $173 found 11 hours ago
Frontier Airlines
Thu, May 7 - Tue, May 19
LAX
Los Angeles Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$195 Roundtrip, found 6 days ago
$195
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, May 7 from Los Angeles Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, May 19, priced at $195 found 6 days ago
Frontier Airlines
Sat, May 23 - Tue, May 26
LAX
Los Angeles Intl.
DCA
Ronald Reagan Washington National
$205 Roundtrip, found 3 days ago
$205
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, May 23 from Los Angeles Intl. to Ronald Reagan Washington National, returning Tue, May 26, priced at $205 found 3 days ago
Frontier Airlines
Wed, Jun 3 - Wed, Jun 10
SMF
Sacramento Intl.
IAD
Washington Dulles Intl.
$215 Roundtrip, found 4 hours ago
$215
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Wed, Jun 3 from Sacramento Intl. to Washington Dulles Intl., returning Wed, Jun 10, priced at $215 found 4 hours ago
Frontier Airlines
Sat, May 9 - Sat, May 30
LAX
Los Angeles Intl.
IAD
Washington Dulles Intl.
$215 Roundtrip, found 2 days ago
$215
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, May 9 from Los Angeles Intl. to Washington Dulles Intl., returning Sat, May 30, priced at $215 found 2 days ago
Delta
Sat, May 23 - Wed, May 27
SBA
Santa Barbara Municipal
IAD
Washington Dulles Intl.
$274 Roundtrip, found 4 days ago
$274
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, May 23 from Santa Barbara Municipal to Washington Dulles Intl., returning Wed, May 27, priced at $274 found 4 days ago
Alaska Airlines
Tue, May 19 - Sat, May 30
LAX
Los Angeles Intl.
DCA
Ronald Reagan Washington National
$294 Roundtrip, found 12 hours ago
$294
Roundtrip
found 12 hours ago
Select Alaska Airlines flight, departing Tue, May 19 from Los Angeles Intl. to Ronald Reagan Washington National, returning Sat, May 30, priced at $294 found 12 hours ago
Delta
Tue, Jun 2 - Fri, Jun 5
SMF
Sacramento Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$308 Roundtrip, found 6 days ago
$308
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Jun 2 from Sacramento Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Fri, Jun 5, priced at $308 found 6 days ago
Delta
Tue, Jun 2 - Tue, Jun 9
SMF
Sacramento Intl.
DCA
Ronald Reagan Washington National
$336 Roundtrip, found 1 day ago
$336
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jun 2 from Sacramento Intl. to Ronald Reagan Washington National, returning Tue, Jun 9, priced at $336 found 1 day ago
Etihad Airways
Thu, Jun 18 - Tue, Jul 14
HYD
Rajiv Gandhi Intl.
IAD
Washington Dulles Intl.
$952 Roundtrip, found 1 day ago
$952
Roundtrip
found 1 day ago
Select Etihad Airways flight, departing Thu, Jun 18 from Rajiv Gandhi Intl. to Washington Dulles Intl., returning Tue, Jul 14, priced at $952 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 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 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 $56, 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 $56 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 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! (1,066 reviews)
Parking was close and well lit

Reviewed on Apr 17, 2026

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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 WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,448 reviews)
Facility is always clean and staff is great

Reviewed on Apr 26, 2026

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Microtel 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! (1,006 reviews)
Beautiful hotel. They just need to bring the price down a little.

Reviewed on Apr 26, 2026

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The George Washington Hotel, A Wyndham Grand Hotel
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)
Good for an overnight stay on our way up north.

Reviewed on Apr 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 ...
9.2/10 Wonderful! (2,265 reviews)
Place is always clean, staff is great. Convenient location

Reviewed on Apr 27, 2026

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La Quinta Inn & Suites by Wyndham Winchester
Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

2.5 out of 5
195 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 ...
9.4/10 Exceptional! (1,106 reviews)
The hotel is convenient to the highway and dining options. The rooms are comfortable. It is a great option for an overnight stay while con a road trip.

Reviewed on Apr 26, 2026

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Comfort Inn & Suites Winchester
APM Inn & Suites

APM Inn & Suites

2 out of 5
1347 Berryville Ave Winchester VA
Stay at this hotel in Winchester. Enjoy free WiFi, free parking, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions ...
6.8/10 (414 reviews)
Bed

Reviewed on Apr 22, 2026

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APM Inn & Suites
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! (965 reviews)
Property did show somewhere. Front desk manager check-in did not break a smile, but did his job. The following morning the front desk staff and café staff were terrific. The room was large.

Reviewed on Apr 22, 2026

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Courtyard by Marriott Winchester
See all 2,083 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.