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Winchester

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Winchester Flights as Low as $122

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

Spirit Airlines
Sun, Jun 1 - Thu, Jun 5
RDU
Raleigh - Durham Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$122 Roundtrip, found 9 hours ago
$122
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Sun, Jun 1 from Raleigh - Durham Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, Jun 5, priced at $122 found 9 hours ago
Spirit Airlines
Thu, May 29 - Thu, Jun 5
RDU
Raleigh - Durham Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$132 Roundtrip, found 9 hours ago
$132
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Thu, May 29 from Raleigh - Durham Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, Jun 5, priced at $132 found 9 hours ago
Frontier Airlines
Fri, May 16 - Sat, May 17
GRR
Gerald R. Ford Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$170 Roundtrip, found 1 day ago
$170
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, May 16 from Gerald R. Ford Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, May 17, priced at $170 found 1 day ago
Frontier Airlines
Tue, Apr 15 - Mon, Apr 28
RDU
Raleigh - Durham Intl.
IAD
Washington Dulles Intl.
$171 Roundtrip, found 6 days ago
$171
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, Apr 15 from Raleigh - Durham Intl. to Washington Dulles Intl., returning Mon, Apr 28, priced at $171 found 6 days ago
American Airlines
Fri, May 16 - Tue, May 20
GRR
Gerald R. Ford Intl.
DCA
Ronald Reagan Washington National
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, May 16 from Gerald R. Ford Intl. to Ronald Reagan Washington National, returning Tue, May 20, priced at $177 found 1 day ago
United
Wed, Oct 8 - Sat, Oct 11
RDU
Raleigh - Durham Intl.
IAD
Washington Dulles Intl.
$179 Roundtrip, found 5 days ago
$179
Roundtrip
found 5 days ago
Select United flight, departing Wed, Oct 8 from Raleigh - Durham Intl. to Washington Dulles Intl., returning Sat, Oct 11, priced at $179 found 5 days ago
Delta
Fri, May 30 - Sun, Jun 8
RDU
Raleigh - Durham Intl.
DCA
Ronald Reagan Washington National
$182 Roundtrip, found 9 hours ago
$182
Roundtrip
found 9 hours ago
Select Delta flight, departing Fri, May 30 from Raleigh - Durham Intl. to Ronald Reagan Washington National, returning Sun, Jun 8, priced at $182 found 9 hours ago
Delta
Fri, May 16 - Tue, May 20
GRR
Gerald R. Ford Intl.
IAD
Washington Dulles Intl.
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, May 16 from Gerald R. Ford Intl. to Washington Dulles Intl., returning Tue, May 20, priced at $197 found 1 day ago
Delta
Fri, May 16 - Tue, May 20
LAN
Capital Region Intl.
DCA
Ronald Reagan Washington National
$199 Roundtrip, found 10 hours ago
$199
Roundtrip
found 10 hours ago
Select Delta flight, departing Fri, May 16 from Capital Region Intl. to Ronald Reagan Washington National, returning Tue, May 20, priced at $199 found 10 hours ago
American Airlines
Fri, May 23 - Tue, May 27
ABI
Abilene Regional
DCA
Ronald Reagan Washington National
$303 Roundtrip, found 1 day ago
$303
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, May 23 from Abilene Regional to Ronald Reagan Washington National, returning Tue, May 27, priced at $303 found 1 day ago
Delta
Tue, Jul 1 - Tue, Jul 8
PSC
Tri-Cities
IAD
Washington Dulles Intl.
$319 Roundtrip, found 20 hours ago
$319
Roundtrip
found 20 hours ago
Select Delta flight, departing Tue, Jul 1 from Tri-Cities to Washington Dulles Intl., returning Tue, Jul 8, priced at $319 found 20 hours ago
Delta
Wed, Jul 2 - Sat, Jul 12
PSC
Tri-Cities
DCA
Ronald Reagan Washington National
$319 Roundtrip, found 20 hours ago
$319
Roundtrip
found 20 hours ago
Select Delta flight, departing Wed, Jul 2 from Tri-Cities to Ronald Reagan Washington National, returning Sat, Jul 12, priced at $319 found 20 hours ago
Delta
Wed, Jul 2 - Tue, Jul 8
PSC
Tri-Cities
BWI
Baltimore Washington Intl. Thurgood Marshall
$331 Roundtrip, found 20 hours ago
$331
Roundtrip
found 20 hours ago
Select Delta flight, departing Wed, Jul 2 from Tri-Cities to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Jul 8, priced at $331 found 20 hours ago
Alaska Airlines
Wed, Jul 2 - Tue, Jul 8
PSC
Tri-Cities
IAD
Washington Dulles Intl.
$398 Roundtrip, found 20 hours ago
$398
Roundtrip
found 20 hours ago
Select Alaska Airlines flight, departing Wed, Jul 2 from Tri-Cities to Washington Dulles Intl., returning Tue, Jul 8, priced at $398 found 20 hours ago
JetBlue Airways
Mon, Jun 2 - Thu, Jun 5
RDU
Raleigh - Durham Intl.
DCA
Ronald Reagan Washington National
$413 Roundtrip, found 9 hours ago
$413
Roundtrip
found 9 hours ago
Select JetBlue Airways flight, departing Mon, Jun 2 from Raleigh - Durham Intl. to Ronald Reagan Washington National, returning Thu, Jun 5, priced at $413 found 9 hours ago
Hawaiian Airlines
Thu, Jul 3 - Thu, Jul 10
PSC
Tri-Cities
IAD
Washington Dulles Intl.
$435 Roundtrip, found 20 hours ago
$435
Roundtrip
found 20 hours ago
Select Hawaiian Airlines flight, departing Thu, Jul 3 from Tri-Cities to Washington Dulles Intl., returning Thu, Jul 10, priced at $435 found 20 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 June, 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 $122, 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 $122 right now, why wait?

Winchester Flight Information
Destination airport
Baltimore Washington Intl. Thurgood Marshall
Destination airport IATA code
BWI
Roundtrip price
$121

Last Minute Hotel Deals in Winchester

La Quinta Inn & Suites by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester
2.5 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
The price is $114 per night from Apr 20 to Apr 21
$114
includes taxes & fees
Apr 20 - Apr 21
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 ...
9/10 Wonderful! (1,922 reviews)
Great, except for the breakfasts
"La Quinta is great overall, but not their breakfasts. I appreciate that they offer it, but I couldn’t eat it."

Reviewed on Apr 10, 2025

La Quinta Inn & Suites by Wyndham Winchester
Comfort Inn & Suites
Comfort Inn & Suites
2.5 out of 5
195 Kernstown Commons Blvd, Winchester, VA
The price is $99 per night from Apr 20 to Apr 21
$99
includes taxes & fees
Apr 20 - Apr 21
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)
"Very clean hotel!! Front desk staff was friendly. Bed was quite firm, so if you're used to something soft it might be uncomfortable for you. I do wish there had been a fan setting on the heating/cooling unit. I like to have a little white noise to drown out exterior noise while I sleep. The area ..."

Reviewed on Apr 10, 2025

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
The price is $143 per night from Apr 20 to Apr 21
$143
includes taxes & fees
Apr 20 - Apr 21
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)
"Really nice value in the Historic area walking distance to shops and restaurants."

Reviewed on Apr 11, 2025

The George Washington Hotel, A Wyndham Grand Hotel
Spark by Hilton Winchester
Spark by Hilton Winchester
3 out of 5
150 Wingate Dr, Winchester, VA
The price is $105 per night from May 11 to May 12
$105
includes taxes & fees
May 11 - May 12
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and ...
8.8/10 Excellent! (1,001 reviews)
"Very clean and updated."

Reviewed on Apr 8, 2025

Spark by Hilton Winchester
Sleep Inn & Suites
Sleep Inn & Suites
2.5 out of 5
140 Costello Dr, Winchester, VA
The price is $79 per night from May 12 to May 13
$79
includes taxes & fees
May 12 - May 13
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! (999 reviews)
"Pleasant staff and nice accommodations"

Reviewed on Apr 6, 2025

Sleep Inn & Suites
Microtel Inn & Suites by Wyndham Winchester
Microtel Inn & Suites by Wyndham Winchester
2.5 out of 5
150 Faraday Plaza, Winchester, VA
The price is $92 per night from Apr 20 to Apr 21
$92
includes taxes & fees
Apr 20 - Apr 21
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! (1,177 reviews)
"I asked if it was possible to get an early check in and they said come now, noon. My only quibble was the pool was cold and the water looked a little mrky. The room was nice though"

Reviewed on Apr 9, 2025

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
The price is $100 per night from May 11 to May 12
$100
includes taxes & fees
May 11 - May 12
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)
"Nice place with great staff restaurant on site"

Reviewed on Apr 5, 2025

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
The price is $72 per night from Apr 22 to Apr 23
$72
includes taxes & fees
Apr 22 - Apr 23
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! (1,105 reviews)
"Great location right off 81 Clean helpful front desk Decor was dated but clean Would stay here again Cracker Barrel next door Downtown not to be missed about 1 1:2 mile away"

Reviewed on Apr 12, 2025

Travelodge by Wyndham Winchester
See all 1,977 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.