Search Cheap Flights to
Winchester

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Winchester Flights as Low as $109

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

Frontier Airlines
Thu, Jan 15 - Sun, Jan 18
DFW
Dallas-Fort Worth Intl.
IAD
Washington Dulles Intl.
$109 Roundtrip, found 1 day ago
$109
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Jan 15 from Dallas-Fort Worth Intl. to Washington Dulles Intl., returning Sun, Jan 18, priced at $109 found 1 day ago
Frontier Airlines
Fri, Nov 21 - Mon, Nov 24
DTW
Detroit Metropolitan Wayne County
BWI
Baltimore Washington Intl. Thurgood Marshall
$110 Roundtrip, found 4 days ago
$110
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, Nov 21 from Detroit Metropolitan Wayne County to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Nov 24, priced at $110 found 4 days ago
Frontier Airlines
Mon, Nov 17 - Mon, Nov 17
DFW
Dallas-Fort Worth Intl.
DCA
Ronald Reagan Washington National
$121 Roundtrip, found 5 days ago
$121
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Nov 17 from Dallas-Fort Worth Intl. to Ronald Reagan Washington National, returning Mon, Nov 17, priced at $121 found 5 days ago
Spirit Airlines
Thu, Nov 13 - Sun, Nov 16
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$124 Roundtrip, found 5 days ago
$124
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Thu, Nov 13 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Nov 16, priced at $124 found 5 days ago
Spirit Airlines
Sun, Dec 14 - Sun, Dec 21
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$133 Roundtrip, found 1 day ago
$133
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sun, Dec 14 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Dec 21, priced at $133 found 1 day ago
Frontier Airlines
Fri, Dec 5 - Mon, Dec 8
JAX
Jacksonville Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$136 Roundtrip, found 1 day ago
$136
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Dec 5 from Jacksonville Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Dec 8, priced at $136 found 1 day ago
Bargain Flight
Mon, Nov 24 - Thu, Nov 27
DTW
Detroit Metropolitan Wayne County
DCA
Ronald Reagan Washington National
$180 Roundtrip, found 5 days ago
$180
Roundtrip
found 5 days ago
Select Bargain Flight flight, departing Mon, Nov 24 from Detroit Metropolitan Wayne County to Ronald Reagan Washington National, returning Thu, Nov 27, priced at $180 found 5 days ago
American Airlines
Sat, Dec 13 - Sun, Dec 14
JAX
Jacksonville Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$182 Roundtrip, found 1 day ago
$182
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Dec 13 from Jacksonville Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Dec 14, priced at $182 found 1 day ago
Delta
Thu, Nov 27 - Tue, Dec 2
DTW
Detroit Metropolitan Wayne County
IAD
Washington Dulles Intl.
$193 Roundtrip, found 3 days ago
$193
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Nov 27 from Detroit Metropolitan Wayne County to Washington Dulles Intl., returning Tue, Dec 2, priced at $193 found 3 days ago
American Airlines
Thu, Nov 27 - Wed, Dec 3
JAX
Jacksonville Intl.
DCA
Ronald Reagan Washington National
$212 Roundtrip, found 7 hours ago
$212
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Thu, Nov 27 from Jacksonville Intl. to Ronald Reagan Washington National, returning Wed, Dec 3, priced at $212 found 7 hours ago
Delta
Tue, Dec 16 - Wed, Dec 17
DAL
Love Field
BWI
Baltimore Washington Intl. Thurgood Marshall
$221 Roundtrip, found 1 day ago
$221
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Dec 16 from Love Field to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Dec 17, priced at $221 found 1 day ago
Delta
Wed, Dec 17 - Wed, Dec 17
DAL
Love Field
DCA
Ronald Reagan Washington National
$266 Roundtrip, found 1 day ago
$266
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Dec 17 from Love Field to Ronald Reagan Washington National, returning Wed, Dec 17, priced at $266 found 1 day ago
United
Wed, Nov 26 - Sun, Nov 30
JAX
Jacksonville Intl.
IAD
Washington Dulles Intl.
$284 Roundtrip, found 6 days ago
$284
Roundtrip
found 6 days ago
Select United flight, departing Wed, Nov 26 from Jacksonville Intl. to Washington Dulles Intl., returning Sun, Nov 30, priced at $284 found 6 days ago
Delta
Sat, Nov 15 - Mon, Nov 24
DAL
Love Field
IAD
Washington Dulles Intl.
$286 Roundtrip, found 1 day ago
$286
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Nov 15 from Love Field to Washington Dulles Intl., returning Mon, Nov 24, priced at $286 found 1 day ago
Spirit Airlines
Sat, Nov 15 - Sun, Nov 23
BOG
El Dorado Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$345 Roundtrip, found 18 hours ago
$345
Roundtrip
found 18 hours ago
Select Spirit Airlines flight, departing Sat, Nov 15 from El Dorado Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Nov 23, priced at $345 found 18 hours ago
Copa
Sat, Nov 15 - Sun, Nov 23
BOG
El Dorado Intl.
IAD
Washington Dulles Intl.
$451 Roundtrip, found 18 hours ago
$451
Roundtrip
found 18 hours ago
Select Copa flight, departing Sat, Nov 15 from El Dorado Intl. to Washington Dulles Intl., returning Sun, Nov 23, priced at $451 found 18 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 January, 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 $109, 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 $109 right now, why wait?

Winchester Flight Information
Destination airport
Washington Dulles Intl.
Destination airport IATA code
IAD
Roundtrip price
$59

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! (1,122 reviews)
Every thing wAs good

Reviewed on Nov 3, 2025

Get rates
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 ...
9.2/10 Wonderful! (2,200 reviews)
This hotel is so nice and very clean, excellent location and staff is very friendly. I will continue to stay here when I come to Winchester!

Reviewed on Nov 4, 2025

Get rates
La Quinta Inn & Suites by Wyndham Winchester
Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

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! (1,057 reviews)
Yes

Reviewed on Nov 4, 2025

Get rates
Comfort Inn & Suites Winchester
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)
Breakfast great, heating fine

Reviewed on Nov 5, 2025

Get rates
Country Inn & Suites by Radisson, Winchester, VA
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! (1,357 reviews)
Bed was comfortable, room was small and clean, no highway noise, quiet part of town, good selection of places to eat within 5 min drive, staff helpful, breakfast ok - plenty to eat, parking safe and convenient.

Reviewed on Nov 2, 2025

Get rates
Microtel Inn & Suites by Wyndham Winchester
Red Roof Inn Winchester, VA

Red Roof Inn Winchester, VA

2 out of 5
991 Millwood Pike, Winchester, VA
Stay at this hotel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the clean rooms in our reviews. Popular attractions ...
7.4/10 Good! (1,001 reviews)
Good Stay
Good stay for an overnight trip. Kumar treated us like very special people! Clean and very comfortable. Only problem - ADA shower very difficult to use for someone less then 5’4. Reaching the shower head was impossible. Would not recommend this place for special needs.

Reviewed on Oct 22, 2025

Get rates
Red Roof Inn Winchester, VA
Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area

2.5 out of 5
640 East Jubal Early Drive, 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! (1,001 reviews)
Nice room, good breakfast and friendly staff.

Reviewed on Nov 4, 2025

Get rates
Hampton Inn Winchester-University/Mall Area
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)
Clean, nice breaksfast service

Reviewed on Nov 4, 2025

Get rates
Holiday Inn Winchester Se-Historic Gateway by IHG
See all 2,054 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.