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Winchester

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Winchester Flights as Low as $64

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

Spirit Airlines
Thu, Jul 10 - Sat, Jul 12
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$64 Roundtrip, found 9 hours ago
$64
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Thu, Jul 10 from Logan Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Jul 12, priced at $64 found 9 hours ago
Spirit Airlines
Wed, Jul 16 - Sat, Jul 19
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$72 Roundtrip, found 20 hours ago
$72
Roundtrip
found 20 hours ago
Select Spirit Airlines flight, departing Wed, Jul 16 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Jul 19, priced at $72 found 20 hours ago
Spirit Airlines
Thu, Jul 31 - Sat, Aug 2
DTW
Detroit Metropolitan Wayne County
BWI
Baltimore Washington Intl. Thurgood Marshall
$72 Roundtrip, found 1 day ago
$72
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Thu, Jul 31 from Detroit Metropolitan Wayne County to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Aug 2, priced at $72 found 1 day ago
Spirit Airlines
Tue, Jul 15 - Tue, Oct 7
IAH
George Bush Intercontinental
BWI
Baltimore Washington Intl. Thurgood Marshall
$98 Roundtrip, found 2 days ago
$98
Roundtrip
found 2 days 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 $98 found 2 days ago
Frontier Airlines
Fri, Aug 22 - Sun, Aug 24
DTW
Detroit Metropolitan Wayne County
BWI
Baltimore Washington Intl. Thurgood Marshall
$108 Roundtrip, found 18 hours ago
$108
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Fri, Aug 22 from Detroit Metropolitan Wayne County to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Aug 24, priced at $108 found 18 hours ago
Frontier Airlines
Tue, Jul 8 - Tue, Jul 15
MIA
Miami Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$110 Roundtrip, found 1 day ago
$110
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Jul 8 from Miami Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Jul 15, priced at $110 found 1 day ago
Delta
Tue, Oct 28 - Tue, Nov 4
MIA
Miami Intl.
DCA
Ronald Reagan Washington National
$117 Roundtrip, found 2 days ago
$117
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Oct 28 from Miami Intl. to Ronald Reagan Washington National, returning Tue, Nov 4, priced at $117 found 2 days ago
Frontier Airlines
Sat, Jul 5 - Sat, Jul 12
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$131 Roundtrip, found 17 hours ago
$131
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Sat, Jul 5 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Sat, Jul 12, priced at $131 found 17 hours ago
Delta
Sat, Aug 30 - Sat, Aug 30
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$132 Roundtrip, found 1 hour ago
$132
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 $132 found 1 hour ago
American Airlines
Thu, Aug 7 - Thu, Aug 7
BOS
Logan Intl.
DCA
Ronald Reagan Washington National
$137 Roundtrip, found 4 hours ago
$137
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Thu, Aug 7 from Logan Intl. to Ronald Reagan Washington National, returning Thu, Aug 7, priced at $137 found 4 hours ago
Delta
Mon, Aug 25 - Tue, Sep 2
DTW
Detroit Metropolitan Wayne County
IAD
Washington Dulles Intl.
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Aug 25 from Detroit Metropolitan Wayne County to Washington Dulles Intl., returning Tue, Sep 2, priced at $157 found 1 day ago
American Airlines
Tue, Aug 26 - Wed, Sep 3
DTW
Detroit Metropolitan Wayne County
DCA
Ronald Reagan Washington National
$157 Roundtrip, found 21 hours ago
$157
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Tue, Aug 26 from Detroit Metropolitan Wayne County to Ronald Reagan Washington National, returning Wed, Sep 3, priced at $157 found 21 hours ago
United
Thu, Jul 10 - Sun, Jul 13
BOS
Logan Intl.
IAD
Washington Dulles Intl.
$171 Roundtrip, found 5 days ago
$171
Roundtrip
found 5 days ago
Select United flight, departing Thu, Jul 10 from Logan Intl. to Washington Dulles Intl., returning Sun, Jul 13, priced at $171 found 5 days ago
Frontier Airlines
Thu, Jun 19 - Thu, Jun 26
MIA
Miami Intl.
IAD
Washington Dulles Intl.
$206 Roundtrip, found 3 hours ago
$206
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Thu, Jun 19 from Miami Intl. to Washington Dulles Intl., returning Thu, Jun 26, priced at $206 found 3 hours ago
Frontier Airlines
Thu, Aug 28 - Sat, Aug 30
IAH
George Bush Intercontinental
IAD
Washington Dulles Intl.
$218 Roundtrip, found 3 days ago
$218
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Aug 28 from George Bush Intercontinental to Washington Dulles Intl., returning Sat, Aug 30, priced at $218 found 3 days ago
Delta
Wed, Jul 16 - Tue, Jul 22
IAH
George Bush Intercontinental
DCA
Ronald Reagan Washington National
$242 Roundtrip, found 4 days ago
$242
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Jul 16 from George Bush Intercontinental to Ronald Reagan Washington National, returning Tue, Jul 22, priced at $242 found 4 days 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 July, 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 $64, 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 $64 right now, why wait?

Winchester Flight Information
Destination airport
Baltimore Washington Intl. Thurgood Marshall
Destination airport IATA code
BWI
Roundtrip price
$64

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! (2,048 reviews)
"Needed a place to sleep for the night with two kids. Room was spacious, clean, comfy. Kids enjoyed the pool (even though it’s not heated) I was able to blast the AC - and use the black out shades. That’s my favorite part of hotels! La Quinta doesn’t disappoint"

Reviewed on Jun 12, 2025

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La Quinta 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! (1,000 reviews)
"It was at best average."

Reviewed on Jun 9, 2025

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Holiday Inn Winchester Se-Historic Gateway by IHG
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! (1,106 reviews)
"The property was old but it was clean, quiet and well maintained. Thanks!"

Reviewed on Jun 12, 2025

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Travelodge 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! (1,254 reviews)
"The hotel was clean and modern. Loved having a Sheetz next door!"

Reviewed on Jun 12, 2025

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Microtel Inn & Suites by Wyndham Winchester
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! (1,008 reviews)
"Convenient location! Great staff! Nice staff & amenities- we’ll be staying here again!"

Reviewed on Jun 9, 2025

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Comfort Inn & Suites
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! (1,000 reviews)
"Perfect hotel in a great location!!!"

Reviewed on Jun 4, 2025

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The George Washington Hotel, A Wyndham Grand Hotel
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! (1,000 reviews)
"Always very easy checkin and nice facility"

Reviewed on Jun 9, 2025

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Country Inn & Suites by Radisson, Winchester, VA
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)
"Easy access from the interstate. I recommend."

Reviewed on Jun 10, 2025

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Sleep Inn & Suites
See all 1,978 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.