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Winchester

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Winchester Flights as Low as $59

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

Frontier Airlines
Thu, Sep 4 - Sun, Sep 7
MIA
Miami Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$59 Roundtrip, found 2 days ago
$59
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Sep 4 from Miami Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Sep 7, priced at $59 found 2 days ago
Spirit Airlines
Sat, Jul 19 - Tue, Jul 22
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$68 Roundtrip, found 1 day ago
$68
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, Jul 19 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Jul 22, priced at $68 found 1 day ago
Frontier Airlines
Mon, Sep 15 - Wed, Sep 17
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$89 Roundtrip, found 1 day ago
$89
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Sep 15 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Wed, Sep 17, priced at $89 found 1 day ago
Spirit Airlines
Wed, Jul 23 - Tue, Jul 29
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$92 Roundtrip, found 1 day ago
$92
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, Jul 23 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Jul 29, priced at $92 found 1 day ago
Frontier Airlines
Sat, Aug 30 - Sat, Aug 30
DFW
Dallas-Fort Worth Intl.
IAD
Washington Dulles Intl.
$94 Roundtrip, found 2 days ago
$94
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Aug 30 from Dallas-Fort Worth Intl. to Washington Dulles Intl., returning Sat, Aug 30, priced at $94 found 2 days ago
Frontier Airlines
Thu, Jul 10 - Sun, Jul 13
MIA
Miami Intl.
IAD
Washington Dulles Intl.
$111 Roundtrip, found 5 days ago
$111
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Jul 10 from Miami Intl. to Washington Dulles Intl., returning Sun, Jul 13, priced at $111 found 5 days ago
Spirit Airlines
Tue, Aug 26 - Wed, Sep 3
IAH
George Bush Intercontinental
BWI
Baltimore Washington Intl. Thurgood Marshall
$115 Roundtrip, found 1 day ago
$115
Roundtrip
found 1 day 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 $115 found 1 day ago
American Airlines
Thu, Jul 24 - Mon, Jul 28
MIA
Miami Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$131 Roundtrip, found 2 days ago
$131
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Jul 24 from Miami Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Jul 28, priced at $131 found 2 days ago
Delta
Sat, Aug 30 - Sat, Aug 30
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$134 Roundtrip, found 1 hour ago
$134
Roundtrip
found 1 hour ago
Select Delta flight, departing Sat, Aug 30 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Sat, Aug 30, priced at $134 found 1 hour ago
American Airlines
Sat, Aug 9 - Wed, Aug 13
DFW
Dallas-Fort Worth Intl.
DCA
Ronald Reagan Washington National
$142 Roundtrip, just found
$142
Roundtrip
just found
Select American Airlines flight, departing Sat, Aug 9 from Dallas-Fort Worth Intl. to Ronald Reagan Washington National, returning Wed, Aug 13, priced at $142 just found
American Airlines
Tue, Oct 28 - Tue, Nov 4
MIA
Miami Intl.
DCA
Ronald Reagan Washington National
$147 Roundtrip, found 2 days ago
$147
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Oct 28 from Miami Intl. to Ronald Reagan Washington National, returning Tue, Nov 4, priced at $147 found 2 days ago
United
Tue, Oct 28 - Tue, Nov 4
IAH
George Bush Intercontinental
DCA
Ronald Reagan Washington National
$177 Roundtrip, found 3 days ago
$177
Roundtrip
found 3 days ago
Select United flight, departing Tue, Oct 28 from George Bush Intercontinental to Ronald Reagan Washington National, returning Tue, Nov 4, priced at $177 found 3 days ago
Frontier Airlines
Fri, Aug 22 - Tue, Sep 2
IAH
George Bush Intercontinental
IAD
Washington Dulles Intl.
$185 Roundtrip, found 2 days ago
$185
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Aug 22 from George Bush Intercontinental to Washington Dulles Intl., returning Tue, Sep 2, priced at $185 found 2 days ago
Delta
Sat, Oct 4 - Sat, Oct 4
DAL
Love Field
BWI
Baltimore Washington Intl. Thurgood Marshall
$231 Roundtrip, found 9 hours ago
$231
Roundtrip
found 9 hours 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 9 hours ago
Delta
Sat, Aug 30 - Sat, Aug 30
DAL
Love Field
IAD
Washington Dulles Intl.
$235 Roundtrip, found 9 hours ago
$235
Roundtrip
found 9 hours ago
Select Delta flight, departing Sat, Aug 30 from Love Field to Washington Dulles Intl., returning Sat, Aug 30, priced at $235 found 9 hours ago
Delta
Fri, Aug 8 - Thu, Aug 14
DAL
Love Field
DCA
Ronald Reagan Washington National
$237 Roundtrip, found 9 hours ago
$237
Roundtrip
found 9 hours ago
Select Delta flight, departing Fri, Aug 8 from Love Field to Ronald Reagan Washington National, returning Thu, Aug 14, priced at $237 found 9 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 $59, 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 $59 right now, why wait?

Winchester Flight Information
Destination airport
Baltimore Washington Intl. Thurgood Marshall
Destination airport IATA code
BWI
Roundtrip price
$67

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 breakfast and the helpful staff in our reviews. ...
8.4/10 Very Good! (1,119 reviews)
"Good place for the price, complimentary breakfast was nice"

Reviewed on Jul 3, 2025

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Travelodge by Wyndham 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! (2,071 reviews)
"Clean spacious nice staff"

Reviewed on Jun 27, 2025

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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 WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,290 reviews)
"Very clean, quiet and comfortable."

Reviewed on Jul 3, 2025

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Microtel 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)
"It’s a lovely property. Clean, updated, and friendly staff."

Reviewed on Jun 30, 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! (1,004 reviews)
"Really nice hotel. So clean! Wonderful atmosphere!"

Reviewed on Jun 30, 2025

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Comfort Inn & Suites
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! (1,001 reviews)
Nice stay!
"Nice stay. Everything was clean and comfortable. Breakfast was good. Friendly staff. Would definitely stay here again."

Reviewed on Jul 2, 2025

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Country Inn & Suites by Radisson, Winchester, VA
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! (1,001 reviews)
"Beautiful old world hotel. Good service, good food and Excellent coffee. Better than any hotel I have stayed at, coffee-wise."

Reviewed on Jul 2, 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 ...
7.8/10 Good! (1,006 reviews)
"Dated but very clean"

Reviewed on Jun 23, 2025

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Sleep Inn & Suites
See all 1,999 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.