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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
Sun, Sep 6 - Fri, Sep 11
CLT
Charlotte-Douglas Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$56 Roundtrip, found 3 hours ago
$56
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sun, Sep 6 from Charlotte-Douglas Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Fri, Sep 11, priced at $56 found 3 hours ago
Southwest Airlines
Sun, Sep 6 - Fri, Sep 11
CLT
Charlotte-Douglas Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$158 Roundtrip, found 3 hours ago
$158
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Sun, Sep 6 from Charlotte-Douglas Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Fri, Sep 11, priced at $158 found 3 hours ago
American Airlines
Sun, Sep 6 - Fri, Sep 11
CLT
Charlotte-Douglas Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$161 Roundtrip, found 3 hours ago
$161
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Sun, Sep 6 from Charlotte-Douglas Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Fri, Sep 11, priced at $161 found 3 hours ago
United
Mon, Sep 21 - Fri, Oct 2
CLT
Charlotte-Douglas Intl.
IAD
Washington Dulles Intl.
$236 Roundtrip, found 4 days ago
$236
Roundtrip
found 4 days ago
Select United flight, departing Mon, Sep 21 from Charlotte-Douglas Intl. to Washington Dulles Intl., returning Fri, Oct 2, priced at $236 found 4 days ago
Delta
Sun, Nov 22 - Thu, Nov 26
CAE
Columbia Metropolitan
DCA
Ronald Reagan Washington National
$279 Roundtrip, found 22 hours ago
$279
Roundtrip
found 22 hours ago
Select Delta flight, departing Sun, Nov 22 from Columbia Metropolitan to Ronald Reagan Washington National, returning Thu, Nov 26, priced at $279 found 22 hours ago
Delta
Sun, Nov 22 - Wed, Dec 2
CAE
Columbia Metropolitan
IAD
Washington Dulles Intl.
$279 Roundtrip, found 21 hours ago
$279
Roundtrip
found 21 hours ago
Select Delta flight, departing Sun, Nov 22 from Columbia Metropolitan to Washington Dulles Intl., returning Wed, Dec 2, priced at $279 found 21 hours ago
Delta
Wed, Nov 18 - Sat, Dec 5
MLI
Quad City Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$295 Roundtrip, found 3 days ago
$295
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Nov 18 from Quad City Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Dec 5, priced at $295 found 3 days ago
United
Sat, Aug 15 - Tue, Aug 18
MLI
Quad City Intl.
DCA
Ronald Reagan Washington National
$361 Roundtrip, found 17 hours ago
$361
Roundtrip
found 17 hours ago
Select United flight, departing Sat, Aug 15 from Quad City Intl. to Ronald Reagan Washington National, returning Tue, Aug 18, priced at $361 found 17 hours ago
United
Sat, Aug 15 - Tue, Aug 18
MLI
Quad City Intl.
IAD
Washington Dulles Intl.
$361 Roundtrip, found 17 hours ago
$361
Roundtrip
found 17 hours ago
Select United flight, departing Sat, Aug 15 from Quad City Intl. to Washington Dulles Intl., returning Tue, Aug 18, priced at $361 found 17 hours ago
Delta
Fri, Oct 30 - Tue, Nov 17
TLH
Tallahassee Intl.
IAD
Washington Dulles Intl.
$383 Roundtrip, found 1 day ago
$383
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Oct 30 from Tallahassee Intl. to Washington Dulles Intl., returning Tue, Nov 17, priced at $383 found 1 day ago
Delta
Sat, Nov 21 - Wed, Dec 2
TLH
Tallahassee Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$387 Roundtrip, found 6 days ago
$387
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Nov 21 from Tallahassee Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Dec 2, priced at $387 found 6 days ago
American Airlines
Wed, Aug 12 - Sat, Aug 15
CAE
Columbia Metropolitan
BWI
Baltimore Washington Intl. Thurgood Marshall
$394 Roundtrip, found 21 hours ago
$394
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Wed, Aug 12 from Columbia Metropolitan to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Aug 15, priced at $394 found 21 hours ago
American Airlines
Thu, Oct 15 - Sat, Oct 17
TLH
Tallahassee Intl.
DCA
Ronald Reagan Washington National
$432 Roundtrip, found 1 day ago
$432
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Oct 15 from Tallahassee Intl. to Ronald Reagan Washington National, returning Sat, Oct 17, priced at $432 found 1 day ago
Air Canada
Mon, Sep 14 - Thu, Oct 1
BDA
L.F. Wade Intl.
DCA
Ronald Reagan Washington National
$444 Roundtrip, found 19 hours ago
$444
Roundtrip
found 19 hours ago
Select Air Canada flight, departing Mon, Sep 14 from L.F. Wade Intl. to Ronald Reagan Washington National, returning Thu, Oct 1, priced at $444 found 19 hours ago
Air Canada
Sun, Sep 13 - Tue, Sep 22
BDA
L.F. Wade Intl.
IAD
Washington Dulles Intl.
$444 Roundtrip, found 19 hours ago
$444
Roundtrip
found 19 hours ago
Select Air Canada flight, departing Sun, Sep 13 from L.F. Wade Intl. to Washington Dulles Intl., returning Tue, Sep 22, priced at $444 found 19 hours ago
American Airlines
Tue, Aug 18 - Tue, Aug 25
BDA
L.F. Wade Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$518 Roundtrip, found 19 hours ago
$518
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Tue, Aug 18 from L.F. Wade Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Aug 25, priced at $518 found 19 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 September, 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
$62

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! (1,021 reviews)
"Nice sized room & bathroom. Nice shower. Dove shampoo. Good tasting breakfast nice polite staff I worth the price.not much noise I slept well. The pool looked fine. There was a bar but I didnt use any t. I really enjoyed my time there"

Reviewed on Aug 10, 2026

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Holiday Inn Winchester Se-Historic Gateway by IHG
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 ...
9.2/10 Wonderful! (1,020 reviews)
"All wonderful"

Reviewed on Aug 11, 2026

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Spark 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 a full-service spa, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
9.4/10 Exceptional! (1,018 reviews)
"Great walking location to everything. Fancy historic building."

Reviewed on Aug 9, 2026

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The George Washington Hotel, A Wyndham Grand Hotel
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! (2,276 reviews)
"I usually have a pretty decent stay, but after driving almost 6 hours and had my three dogs and luggage - the bed was unmade and they were dirty. They put me in another room but dragging all my stuff at 9 pm was not fun. I don’t know if I’ll go back."

Reviewed on Aug 9, 2026

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La Quinta Inn & Suites 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 parking, and a fitness center. Our guests praise the helpful staff and ...
9.2/10 Wonderful! (1,450 reviews)
"Everything was fine with no issues. Pack a night light for the bathroom as the loud fan comes on with the light"

Reviewed on Aug 10, 2026

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Microtel 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! (1,141 reviews)
"Great location near our venue. Great staff. Clean facility. Plenty of places to eat nearby."

Reviewed on Aug 10, 2026

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Comfort Inn & Suites 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. ...
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Travelodge by Wyndham 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. ...
9.2/10 Wonderful! (1,015 reviews)
"Loved that there were several door options available to enter from outside for any room, the room in general was all I needed, the staff was very friendly and helpful!!!!! Loved the mattress and the pool!!"

Reviewed on Aug 11, 2026

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TRU By Hilton Winchester
See all 2,100 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.