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Winchester

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Winchester Flights as Low as $70

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

Spirit Airlines
Sat, Oct 25 - Sat, Nov 1
IAH
George Bush Intercontinental
BWI
Baltimore Washington Intl. Thurgood Marshall
$70 Roundtrip, found 2 days ago
$70
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sat, Oct 25 from George Bush Intercontinental to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Nov 1, priced at $70 found 2 days ago
Spirit Airlines
Sat, Sep 6 - Tue, Sep 9
DTW
Detroit Metropolitan Wayne County
BWI
Baltimore Washington Intl. Thurgood Marshall
$72 Roundtrip, found 7 hours ago
$72
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Sat, Sep 6 from Detroit Metropolitan Wayne County to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Sep 9, priced at $72 found 7 hours ago
Spirit Airlines
Wed, Sep 10 - Sat, Sep 13
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$80 Roundtrip, found 20 hours ago
$80
Roundtrip
found 20 hours ago
Select Spirit Airlines flight, departing Wed, Sep 10 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Sep 13, priced at $80 found 20 hours ago
Frontier Airlines
Sat, Sep 13 - Wed, Sep 17
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$88 Roundtrip, found 2 hours ago
$88
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sat, Sep 13 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Sep 17, priced at $88 found 2 hours ago
Frontier Airlines
Sat, Oct 25 - Sun, Oct 26
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$100 Roundtrip, found 6 days ago
$100
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Oct 25 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Sun, Oct 26, priced at $100 found 6 days ago
Frontier Airlines
Fri, Sep 12 - Mon, Sep 15
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$104 Roundtrip, found 2 hours ago
$104
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Fri, Sep 12 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Sep 15, priced at $104 found 2 hours ago
American Airlines
Fri, Nov 14 - Sun, Nov 16
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$137 Roundtrip, found 4 hours ago
$137
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Fri, Nov 14 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Sun, Nov 16, priced at $137 found 4 hours ago
American Airlines
Wed, Sep 17 - Sun, Sep 21
DFW
Dallas-Fort Worth Intl.
IAD
Washington Dulles Intl.
$153 Roundtrip, found 5 days ago
$153
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Sep 17 from Dallas-Fort Worth Intl. to Washington Dulles Intl., returning Sun, Sep 21, priced at $153 found 5 days ago
United
Tue, Oct 28 - Tue, Nov 4
IAH
George Bush Intercontinental
DCA
Ronald Reagan Washington National
$157 Roundtrip, found 2 days ago
$157
Roundtrip
found 2 days ago
Select United flight, departing Tue, Oct 28 from George Bush Intercontinental to Ronald Reagan Washington National, returning Tue, Nov 4, priced at $157 found 2 days ago
United
Wed, Sep 10 - Tue, Sep 23
IAH
George Bush Intercontinental
IAD
Washington Dulles Intl.
$161 Roundtrip, found 4 days ago
$161
Roundtrip
found 4 days ago
Select United flight, departing Wed, Sep 10 from George Bush Intercontinental to Washington Dulles Intl., returning Tue, Sep 23, priced at $161 found 4 days ago
Bargain Flight
Tue, Aug 26 - Wed, Sep 3
DTW
Detroit Metropolitan Wayne County
DCA
Ronald Reagan Washington National
$168 Roundtrip, found 1 day ago
$168
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Tue, Aug 26 from Detroit Metropolitan Wayne County to Ronald Reagan Washington National, returning Wed, Sep 3, priced at $168 found 1 day ago
United
Thu, Sep 11 - Sun, Sep 14
DTW
Detroit Metropolitan Wayne County
IAD
Washington Dulles Intl.
$183 Roundtrip, found 4 days ago
$183
Roundtrip
found 4 days ago
Select United flight, departing Thu, Sep 11 from Detroit Metropolitan Wayne County to Washington Dulles Intl., returning Sun, Sep 14, priced at $183 found 4 days ago
American Airlines
Sat, Sep 20 - Sun, Sep 21
DFW
Dallas-Fort Worth Intl.
DCA
Ronald Reagan Washington National
$186 Roundtrip, found 5 days ago
$186
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Sep 20 from Dallas-Fort Worth Intl. to Ronald Reagan Washington National, returning Sun, Sep 21, priced at $186 found 5 days ago
Delta
Sat, Oct 4 - Sat, Oct 4
DAL
Love Field
BWI
Baltimore Washington Intl. Thurgood Marshall
$236 Roundtrip, found 1 day ago
$236
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Oct 4 from Love Field to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Oct 4, priced at $236 found 1 day ago
Delta
Wed, Sep 17 - Sun, Sep 21
DAL
Love Field
IAD
Washington Dulles Intl.
$294 Roundtrip, found 5 days ago
$294
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Sep 17 from Love Field to Washington Dulles Intl., returning Sun, Sep 21, priced at $294 found 5 days ago
Delta
Mon, Aug 18 - Tue, Aug 19
DAL
Love Field
DCA
Ronald Reagan Washington National
$353 Roundtrip, found 1 day ago
$353
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Aug 18 from Love Field to Ronald Reagan Washington National, returning Tue, Aug 19, priced at $353 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 October, 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 15 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 $70, 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 $70 right now, why wait?

Winchester Flight Information
Destination airport
Baltimore Washington Intl. Thurgood Marshall
Destination airport IATA code
BWI
Roundtrip price
$70

Last Minute Hotel Deals in 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
Stay at this 3-star 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! (2,126 reviews)
"Enjoyed it!"

Reviewed on Aug 12, 2025

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La Quinta Inn & Suites 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
Stay at this 3-star 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)
"Bed comfort"

Reviewed on Aug 12, 2025

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Holiday Inn Winchester Se-Historic Gateway by IHG
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 ...
9/10 Wonderful! (1,324 reviews)
Economical, spotless
"Great price , spotlessly clean. Have stayed here several times for one night, will stay again!"

Reviewed on Aug 10, 2025

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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
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free parking, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
8.8/10 Excellent! (856 reviews)
"Beds were comfortable and staff were very nice."

Reviewed on Aug 10, 2025

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Courtyard by Marriott 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
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,003 reviews)
"Clean comfortable"

Reviewed on Aug 8, 2025

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Country Inn & Suites by Radisson, Winchester, VA
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! (1,008 reviews)
"Excellent customer service!!! Both front desk guys were super helpful! Also woman running breakfast by herself on a VERY busy morning did a great job keeping breakfast stocked!! Work ethic in this location is A+"

Reviewed on Aug 12, 2025

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Comfort Inn & Suites 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
Stay at this 3.5-star spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff in our ...
9.2/10 Wonderful! (1,007 reviews)
"Bed comfy, dinner delicious. Lovely ambiance in lobby and enjoyed pool."

Reviewed on Aug 10, 2025

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The George Washington Hotel, A Wyndham Grand Hotel
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! (682 reviews)
"We will be coming back that way often we will Rebook again it was bet clean, staff efficient, breakfast wonderful. It was a great choice in hotels."

Reviewed on Aug 10, 2025

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SpringHill Suites by Marriott Winchester
See all 1,993 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.