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Winchester

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Winchester Flights as Low as $72

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

Spirit Airlines
Sat, May 31 - Wed, Jun 4
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$72 Roundtrip, found 2 days ago
$72
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sat, May 31 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Jun 4, priced at $72 found 2 days ago
Frontier Airlines
Mon, Jun 2 - Mon, Jun 2
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$96 Roundtrip, found 2 days ago
$96
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Jun 2 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Jun 2, priced at $96 found 2 days ago
Spirit Airlines
Thu, Jun 12 - Mon, Jun 16
TPA
Tampa Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$108 Roundtrip, found 2 hours ago
$108
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Thu, Jun 12 from Tampa Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Jun 16, priced at $108 found 2 hours ago
Frontier Airlines
Tue, Jun 24 - Sat, Jul 5
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$111 Roundtrip, found 2 days ago
$111
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Jun 24 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Sat, Jul 5, priced at $111 found 2 days ago
Spirit Airlines
Tue, Jul 15 - Tue, Oct 7
IAH
George Bush Intercontinental
BWI
Baltimore Washington Intl. Thurgood Marshall
$128 Roundtrip, found 4 hours ago
$128
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Tue, Jul 15 from George Bush Intercontinental to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Oct 7, priced at $128 found 4 hours ago
American Airlines
Mon, Jun 30 - Tue, Jul 8
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$136 Roundtrip, found 16 hours ago
$136
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Mon, Jun 30 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Tue, Jul 8, priced at $136 found 16 hours ago
Frontier Airlines
Sun, Jul 13 - Mon, Jul 14
TPA
Tampa Intl.
IAD
Washington Dulles Intl.
$138 Roundtrip, found 5 days ago
$138
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sun, Jul 13 from Tampa Intl. to Washington Dulles Intl., returning Mon, Jul 14, priced at $138 found 5 days ago
American Airlines
Sat, Jun 14 - Sat, Jun 14
TPA
Tampa Intl.
DCA
Ronald Reagan Washington National
$160 Roundtrip, found 4 days ago
$160
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Jun 14 from Tampa Intl. to Ronald Reagan Washington National, returning Sat, Jun 14, priced at $160 found 4 days ago
Frontier Airlines
Tue, Jun 10 - Sat, Jun 14
IAH
George Bush Intercontinental
IAD
Washington Dulles Intl.
$213 Roundtrip, found 12 hours ago
$213
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Tue, Jun 10 from George Bush Intercontinental to Washington Dulles Intl., returning Sat, Jun 14, priced at $213 found 12 hours 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
Tue, Jun 10 - Tue, Jun 10
DAL
Love Field
DCA
Ronald Reagan Washington National
$235 Roundtrip, found 4 days ago
$235
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Jun 10 from Love Field to Ronald Reagan Washington National, returning Tue, Jun 10, priced at $235 found 4 days ago
Delta
Wed, Jul 16 - Sat, Jul 19
DAL
Love Field
IAD
Washington Dulles Intl.
$237 Roundtrip, found 23 hours ago
$237
Roundtrip
found 23 hours ago
Select Delta flight, departing Wed, Jul 16 from Love Field to Washington Dulles Intl., returning Sat, Jul 19, priced at $237 found 23 hours ago
Delta
Tue, Oct 7 - Wed, Oct 8
IAH
George Bush Intercontinental
DCA
Ronald Reagan Washington National
$237 Roundtrip, found 15 hours ago
$237
Roundtrip
found 15 hours ago
Select Delta flight, departing Tue, Oct 7 from George Bush Intercontinental to Ronald Reagan Washington National, returning Wed, Oct 8, priced at $237 found 15 hours ago
American Airlines
Thu, Jun 5 - Tue, Jun 17
SGF
Springfield-Branson National
BWI
Baltimore Washington Intl. Thurgood Marshall
$274 Roundtrip, found 1 day ago
$274
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Jun 5 from Springfield-Branson National to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Jun 17, priced at $274 found 1 day ago
American Airlines
Wed, Jun 4 - Tue, Jun 17
SGF
Springfield-Branson National
IAD
Washington Dulles Intl.
$281 Roundtrip, found 1 day ago
$281
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Jun 4 from Springfield-Branson National to Washington Dulles Intl., returning Tue, Jun 17, priced at $281 found 1 day ago
American Airlines
Wed, Jun 4 - Tue, Jun 17
SGF
Springfield-Branson National
DCA
Ronald Reagan Washington National
$281 Roundtrip, found 1 day ago
$281
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Jun 4 from Springfield-Branson National to Ronald Reagan Washington National, returning Tue, Jun 17, priced at $281 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 May, 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 $72, 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 $72 right now, why wait?

Winchester Flight Information
Destination airport
Baltimore Washington Intl. Thurgood Marshall
Destination airport IATA code
BWI
Roundtrip price
$72

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 ...
9/10 Wonderful! (2,023 reviews)
"clean, affordable, up to date, great indian restaurant around the corner, young lady at the desk was very friendly and helpful"

Reviewed on May 22, 2025

Get rates
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. ...
8.2/10 Very Good! (1,118 reviews)
"We stay here often. Very clean, comfortable beds. Easy on and off highway and plenty of dining choices."

Reviewed on May 22, 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! (1,006 reviews)
"stop on the way to NJ and came back the next day to go home"

Reviewed on May 22, 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 parking, and a fitness center. Our guests praise the helpful staff and ...
9/10 Wonderful! (1,225 reviews)
"We liked everything about our stay. We are going back in a week."

Reviewed on May 17, 2025

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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
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! (1,002 reviews)
"Great property!!"

Reviewed on May 21, 2025

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The George Washington Hotel, A Wyndham Grand Hotel
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 ...
8/10 Very Good! (1,009 reviews)
A Positive Experience
"We have always had a positive experience at this hotel. The rooms are always clean and comfortable, the staff friendly and helpful, and check in/check out is easy. We also appreciate the free breakfast and availability of a pool and exercise room as well as the easy off/easy on location."

Reviewed on May 22, 2025

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Sleep Inn & Suites
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 ...
9.2/10 Wonderful! (1,001 reviews)
"Brand spanking new. Great hotel and fantastic staff."

Reviewed on May 22, 2025

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Comfort Inn & Suites
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! (614 reviews)
"Nice, new, friendly, great breakfast options!"

Reviewed on May 18, 2025

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SpringHill Suites by Marriott Winchester
See all 1,970 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.