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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
Tue, Aug 5 - Tue, Aug 12
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$66 Roundtrip, found 23 hours ago
$66
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Tue, Aug 5 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Aug 12, priced at $66 found 23 hours ago
Spirit Airlines
Tue, Aug 26 - Wed, Sep 3
IAH
George Bush Intercontinental
BWI
Baltimore Washington Intl. Thurgood Marshall
$70 Roundtrip, found 7 hours ago
$70
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Tue, Aug 26 from George Bush Intercontinental to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Sep 3, priced at $70 found 7 hours ago
Spirit Airlines
Mon, Sep 8 - Thu, Sep 11
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$82 Roundtrip, found 1 day ago
$82
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Mon, Sep 8 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, Sep 11, priced at $82 found 1 day ago
Frontier Airlines
Wed, Jul 30 - Sat, Aug 9
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$122 Roundtrip, found 2 days ago
$122
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Jul 30 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Sat, Aug 9, priced at $122 found 2 days ago
Frontier Airlines
Tue, Aug 26 - Sat, Aug 30
DEN
Denver Intl.
DCA
Ronald Reagan Washington National
$123 Roundtrip, found 9 hours ago
$123
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Tue, Aug 26 from Denver Intl. to Ronald Reagan Washington National, returning Sat, Aug 30, priced at $123 found 9 hours ago
United
Sat, Aug 30 - Sat, Aug 30
DFW
Dallas-Fort Worth Intl.
IAD
Washington Dulles Intl.
$134 Roundtrip, found 1 day ago
$134
Roundtrip
found 1 day ago
Select United flight, departing Sat, Aug 30 from Dallas-Fort Worth Intl. to Washington Dulles Intl., returning Sat, Aug 30, priced at $134 found 1 day ago
Delta
Sat, Aug 30 - Sat, Aug 30
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$134 Roundtrip, just found
$134
Roundtrip
just found
Select Delta flight, departing Sat, Aug 30 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Sat, Aug 30, priced at $134 just found
American Airlines
Wed, Aug 27 - Sat, Aug 30
DFW
Dallas-Fort Worth Intl.
DCA
Ronald Reagan Washington National
$139 Roundtrip, found 1 day ago
$139
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Aug 27 from Dallas-Fort Worth Intl. to Ronald Reagan Washington National, returning Sat, Aug 30, priced at $139 found 1 day ago
Frontier Airlines
Fri, Aug 29 - Sun, Aug 31
DEN
Denver Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$164 Roundtrip, found 1 day ago
$164
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Aug 29 from Denver Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Aug 31, priced at $164 found 1 day ago
American Airlines
Thu, Aug 21 - Mon, Aug 25
DEN
Denver Intl.
IAD
Washington Dulles Intl.
$198 Roundtrip, found 1 day ago
$198
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Aug 21 from Denver Intl. to Washington Dulles Intl., returning Mon, Aug 25, priced at $198 found 1 day ago
United
Thu, Aug 7 - Sun, Aug 10
IAH
George Bush Intercontinental
DCA
Ronald Reagan Washington National
$206 Roundtrip, found 6 days ago
$206
Roundtrip
found 6 days ago
Select United flight, departing Thu, Aug 7 from George Bush Intercontinental to Ronald Reagan Washington National, returning Sun, Aug 10, priced at $206 found 6 days ago
United
Thu, Oct 23 - Mon, Oct 27
IAH
George Bush Intercontinental
IAD
Washington Dulles Intl.
$209 Roundtrip, found 3 days ago
$209
Roundtrip
found 3 days ago
Select United flight, departing Thu, Oct 23 from George Bush Intercontinental to Washington Dulles Intl., returning Mon, Oct 27, priced at $209 found 3 days ago
Delta
Sat, Oct 4 - Sat, Oct 4
DAL
Love Field
BWI
Baltimore Washington Intl. Thurgood Marshall
$231 Roundtrip, found 1 day ago
$231
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 $231 found 1 day ago
Delta
Sat, Aug 30 - Sat, Aug 30
DAL
Love Field
IAD
Washington Dulles Intl.
$233 Roundtrip, found 1 day ago
$233
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Aug 30 from Love Field to Washington Dulles Intl., returning Sat, Aug 30, priced at $233 found 1 day ago
Delta
Tue, Aug 12 - Tue, Aug 12
DAL
Love Field
DCA
Ronald Reagan Washington National
$237 Roundtrip, found 6 hours ago
$237
Roundtrip
found 6 hours ago
Select Delta flight, departing Tue, Aug 12 from Love Field to Ronald Reagan Washington National, returning Tue, Aug 12, priced at $237 found 6 hours ago
Delta
Tue, Jul 29 - Sat, Aug 2
MOB
Mobile Regional
BWI
Baltimore Washington Intl. Thurgood Marshall
$320 Roundtrip, found 2 hours ago
$320
Roundtrip
found 2 hours ago
Select Delta flight, departing Tue, Jul 29 from Mobile Regional to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Aug 2, priced at $320 found 2 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 August, 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

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! (2,084 reviews)
"The breakfast was nice, and though the property was smaller than I've seen elsewhere, it was very up-to-date and not a 70s or 80s style. Nice design overall."

Reviewed on Jul 22, 2025

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La Quinta 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 breakfast and the helpful staff in our reviews. ...
8.4/10 Very Good! (1,091 reviews)
"Close to Sportsman 's Warehouse. Short drive to Chick-fil-A. Breakfast was good, as we like a light meal. Room was quiet, slept well on comfy bed."

Reviewed on Jul 17, 2025

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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
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! (1,017 reviews)
"Everything was Ok. The carpet in the hallways is tired. Could be a possible trip hazard to some. An AC in one room barely worked. Breakfast was excellent. Pool area was nice. Your kitchen staff is great. The personnel we met at the service desk were wonderful."

Reviewed on Jul 22, 2025

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Holiday Inn Winchester Se-Historic Gateway by IHG
Comfort Inn & Suites

Comfort Inn & Suites

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)
"Bed was comfortable. Had reasonable breakfast. Able to walk to restaurants and grocery store in same parking lot."

Reviewed on Jul 20, 2025

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Comfort Inn & Suites
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! (1,315 reviews)
DA BOMB
"IT WAS A VERY NICE HOTEL. GREAT LOCATION & LIKE BRAND NEW (OPEN 3YRS BUT NO WEAR & TEAR).)"

Reviewed on Jul 21, 2025

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Microtel Inn & Suites by Wyndham 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! (1,009 reviews)
"."

Reviewed on Jul 21, 2025

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Country Inn & Suites by Radisson, Winchester, VA
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! (661 reviews)
Trip North 2025
"Great accommodation for a traveling couple, spacious, easy to check in, use of luggage cart made it easy to get our belongings to and from the room on the 3rd floor. Good stores nearby (Target) and restaurant (Texas Roadhouse)."

Reviewed on Jul 21, 2025

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SpringHill Suites by Marriott Winchester
Sleep Inn & Suites

Sleep Inn & Suites

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! (1,006 reviews)
"A good stay for the price."

Reviewed on Jul 20, 2025

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Sleep Inn & Suites
See all 1,998 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.