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Winchester

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Winchester Flights as Low as $58

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

Spirit Airlines
Sat, Aug 16 - Tue, Aug 19
DTW
Detroit Metropolitan Wayne County
BWI
Baltimore Washington Intl. Thurgood Marshall
$58 Roundtrip, found 1 hour ago
$58
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, Aug 16 from Detroit Metropolitan Wayne County to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Aug 19, priced at $58 found 1 hour ago
Spirit Airlines
Sat, Jul 19 - Tue, Jul 22
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$72 Roundtrip, just found
$72
Roundtrip
just found
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 $72 just found
Spirit Airlines
Tue, Aug 5 - Wed, Aug 6
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$75 Roundtrip, found 1 day ago
$75
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Aug 5 from Logan Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Aug 6, priced at $75 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 hour ago
$89
Roundtrip
found 1 hour 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 hour ago
Frontier Airlines
Sat, Jul 19 - Mon, Jul 28
SAN
San Diego Intl.
IAD
Washington Dulles Intl.
$127 Roundtrip, found 5 days ago
$127
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Jul 19 from San Diego Intl. to Washington Dulles Intl., returning Mon, Jul 28, priced at $127 found 5 days ago
JetBlue Airways
Mon, Sep 8 - Mon, Sep 8
BOS
Logan Intl.
DCA
Ronald Reagan Washington National
$132 Roundtrip, found 3 hours ago
$132
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Mon, Sep 8 from Logan Intl. to Ronald Reagan Washington National, returning Mon, Sep 8, priced at $132 found 3 hours 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
United
Tue, Aug 26 - Tue, Sep 2
DTW
Detroit Metropolitan Wayne County
IAD
Washington Dulles Intl.
$139 Roundtrip, found 8 hours ago
$139
Roundtrip
found 8 hours ago
Select United flight, departing Tue, Aug 26 from Detroit Metropolitan Wayne County to Washington Dulles Intl., returning Tue, Sep 2, priced at $139 found 8 hours ago
Delta
Tue, Aug 26 - Wed, Sep 3
DTW
Detroit Metropolitan Wayne County
DCA
Ronald Reagan Washington National
$140 Roundtrip, found 3 hours ago
$140
Roundtrip
found 3 hours ago
Select Delta flight, departing Tue, Aug 26 from Detroit Metropolitan Wayne County to Ronald Reagan Washington National, returning Wed, Sep 3, priced at $140 found 3 hours ago
United
Wed, Jul 23 - Mon, Aug 11
BOS
Logan Intl.
IAD
Washington Dulles Intl.
$155 Roundtrip, found 6 hours ago
$155
Roundtrip
found 6 hours ago
Select United flight, departing Wed, Jul 23 from Logan Intl. to Washington Dulles Intl., returning Mon, Aug 11, priced at $155 found 6 hours ago
Delta
Sat, Oct 4 - Sat, Oct 4
DAL
Love Field
BWI
Baltimore Washington Intl. Thurgood Marshall
$231 Roundtrip, found 4 hours ago
$231
Roundtrip
found 4 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 4 hours ago
Bargain Flight
Wed, Sep 3 - Sat, Sep 6
SAN
San Diego Intl.
DCA
Ronald Reagan Washington National
$235 Roundtrip, found 1 day ago
$235
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Wed, Sep 3 from San Diego Intl. to Ronald Reagan Washington National, returning Sat, Sep 6, priced at $235 found 1 day ago
Delta
Sat, Aug 30 - Sat, Aug 30
DAL
Love Field
IAD
Washington Dulles Intl.
$235 Roundtrip, found 5 hours ago
$235
Roundtrip
found 5 hours ago
Select Delta flight, departing Sat, Aug 30 from Love Field to Washington Dulles Intl., returning Sat, Aug 30, priced at $235 found 5 hours ago
Delta
Fri, Aug 8 - Thu, Aug 14
DAL
Love Field
DCA
Ronald Reagan Washington National
$237 Roundtrip, found 15 hours ago
$237
Roundtrip
found 15 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 15 hours ago
Spirit Airlines
Wed, Jul 30 - Mon, Aug 4
SAN
San Diego Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$245 Roundtrip, found 1 hour ago
$245
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Wed, Jul 30 from San Diego Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Aug 4, priced at $245 found 1 hour ago
American Airlines
Wed, Sep 3 - Sat, Sep 6
CLD
McClellan-Palomar
DCA
Ronald Reagan Washington National
$262 Roundtrip, found 11 hours ago
$262
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Wed, Sep 3 from McClellan-Palomar to Ronald Reagan Washington National, returning Sat, Sep 6, priced at $262 found 11 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 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 $58, 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 $58 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

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! (1,112 reviews)
No frills, but clean
"The hotel room was clean no frills, the floor was wet when we got in there. It was a dark brown linoleum. I don’t know why it was wet. Room is acceptable just as stated no-frills."

Reviewed on Jun 28, 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! (1,284 reviews)
"Loved our stay super comfy beds!"

Reviewed on Jun 29, 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! (1,007 reviews)
"Convenient to downtown Winchester, Rt 11 and Stephen City!"

Reviewed on Jun 29, 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! (1,006 reviews)
Would stay again
"It was good. Breakfast had many options and everyone was able to find what they liked. The staff in the morning kept the area clean and were helpful. Several high chairs available"

Reviewed on Jun 29, 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! (1,003 reviews)
"It was a great location! The room was a little small. The staff was friendly and the restaurant and bar were great!"

Reviewed on Jun 27, 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.