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Winchester

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Winchester Flights as Low as $66

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

Frontier Airlines
Sat, Apr 18 - Sat, May 2
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$66 Roundtrip, found 1 hour ago
$66
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Apr 18 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, May 2, priced at $66 found 1 hour ago
Spirit Airlines
Sat, May 2 - Tue, May 12
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$98 Roundtrip, found 5 days ago
$98
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Sat, May 2 from Logan Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, May 12, priced at $98 found 5 days ago
Frontier Airlines
Wed, Apr 29 - Wed, May 20
DEN
Denver Intl.
DCA
Ronald Reagan Washington National
$99 Roundtrip, found 6 days ago
$99
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Apr 29 from Denver Intl. to Ronald Reagan Washington National, returning Wed, May 20, priced at $99 found 6 days ago
Frontier Airlines
Sat, Apr 18 - Sat, May 2
BNA
Nashville Intl.
IAD
Washington Dulles Intl.
$170 Roundtrip, found 4 days ago
$170
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Apr 18 from Nashville Intl. to Washington Dulles Intl., returning Sat, May 2, priced at $170 found 4 days ago
JetBlue Airways
Tue, Mar 10 - Tue, Mar 10
BNA
Nashville Intl.
DCA
Ronald Reagan Washington National
$172 Roundtrip, found 15 hours ago
$172
Roundtrip
found 15 hours ago
Select JetBlue Airways flight, departing Tue, Mar 10 from Nashville Intl. to Ronald Reagan Washington National, returning Tue, Mar 10, priced at $172 found 15 hours ago
JetBlue Airways
Tue, Mar 31 - Tue, Mar 31
BOS
Logan Intl.
DCA
Ronald Reagan Washington National
$176 Roundtrip, found 2 days ago
$176
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Mar 31 from Logan Intl. to Ronald Reagan Washington National, returning Tue, Mar 31, priced at $176 found 2 days ago
Bargain Flight
Sat, Mar 7 - Tue, Mar 17
BOS
Logan Intl.
DCA
Ronald Reagan Washington National
$177 Roundtrip, found 15 hours ago
$177
Roundtrip
found 15 hours ago
Select Bargain Flight flight, departing Sat, Mar 7 from Logan Intl. to Ronald Reagan Washington National, returning Tue, Mar 17, priced at $177 found 15 hours ago
Frontier Airlines
Tue, Feb 17 - Tue, Mar 3
DFW
Dallas-Fort Worth Intl.
DCA
Ronald Reagan Washington National
$178 Roundtrip, found 6 days ago
$178
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, Feb 17 from Dallas-Fort Worth Intl. to Ronald Reagan Washington National, returning Tue, Mar 3, priced at $178 found 6 days ago
Frontier Airlines
Thu, Mar 5 - Thu, Mar 12
DFW
Dallas-Fort Worth Intl.
IAD
Washington Dulles Intl.
$178 Roundtrip, found 4 days ago
$178
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Mar 5 from Dallas-Fort Worth Intl. to Washington Dulles Intl., returning Thu, Mar 12, priced at $178 found 4 days ago
Spirit Airlines
Tue, May 12 - Tue, May 19
BNA
Nashville Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$189 Roundtrip, found 6 days ago
$189
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Tue, May 12 from Nashville Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, May 19, priced at $189 found 6 days ago
United
Mon, Mar 30 - Wed, Apr 1
BOS
Logan Intl.
IAD
Washington Dulles Intl.
$192 Roundtrip, found 2 days ago
$192
Roundtrip
found 2 days ago
Select United flight, departing Mon, Mar 30 from Logan Intl. to Washington Dulles Intl., returning Wed, Apr 1, priced at $192 found 2 days ago
Frontier Airlines
Mon, Mar 2 - Wed, Mar 18
DEN
Denver Intl.
IAD
Washington Dulles Intl.
$193 Roundtrip, found 5 days ago
$193
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Mar 2 from Denver Intl. to Washington Dulles Intl., returning Wed, Mar 18, priced at $193 found 5 days ago
Frontier Airlines
Tue, Mar 17 - Tue, Mar 24
DEN
Denver Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$205 Roundtrip, found 6 days ago
$205
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, Mar 17 from Denver Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Mar 24, priced at $205 found 6 days ago
Delta
Wed, Mar 25 - Wed, Apr 1
DAL
Love Field
IAD
Washington Dulles Intl.
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Mar 25 from Love Field to Washington Dulles Intl., returning Wed, Apr 1, priced at $217 found 1 day ago
Delta
Tue, Mar 3 - Tue, Mar 10
DAL
Love Field
DCA
Ronald Reagan Washington National
$242 Roundtrip, found 6 days ago
$242
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Mar 3 from Love Field to Ronald Reagan Washington National, returning Tue, Mar 10, priced at $242 found 6 days ago
Delta
Sat, Feb 28 - Sat, Feb 28
DAL
Love Field
BWI
Baltimore Washington Intl. Thurgood Marshall
$299 Roundtrip, found 4 days ago
$299
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Feb 28 from Love Field to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Feb 28, priced at $299 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 April, 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 $66, 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 $66 right now, why wait?

Winchester Flight Information
Destination airport
Baltimore Washington Intl. Thurgood Marshall
Destination airport IATA code
BWI
Roundtrip price
$66

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
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! (2,265 reviews)
Staff was very courteous and friendly throught our entire stay! Everything was updated and very clean. Kids LOVED the pool and breakfast.

Reviewed on Feb 10, 2026

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La Quinta Inn & Suites by Wyndham Winchester
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
Book a stay at this spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
9.2/10 Wonderful! (1,002 reviews)
Clean nice room Great location for restaurants

Reviewed on Jan 28, 2026

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The George Washington Hotel, A Wyndham Grand Hotel
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! (1,444 reviews)
The only thing that disappointed me is that the breakfast potatoes and omelets were quite spice. I was unable to eat them. However, the room was excellent.

Reviewed on Feb 10, 2026

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Microtel Inn & Suites by Wyndham 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 helpful staff and the clean rooms in our reviews. ...
8.4/10 Very Good! (1,083 reviews)
Room was good for the price, staff was friendly and helpful

Reviewed on Feb 4, 2026

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Travelodge by Wyndham Winchester
Quality Inn Winchester

Quality Inn Winchester

2.5 out of 5
1601 Martinsburg Pike Winchester VA
Stay at this hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
9.2/10 Wonderful! (1,001 reviews)
The staff (phenomenal), the cleanliness, the attention to detail! The lady overseeing breakfast was a machine. Everything tidied up and perfect. The front desk staff were amazing!! Best staff we've ever seen and we travel a LOT!! 100% recommend staying here. It was less than a mile from the concert ...

Reviewed on Jan 18, 2026

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Quality Inn Winchester
Candlewood Suites Winchester by IHG

Candlewood Suites Winchester by IHG

2.5 out of 5
1135 Millwood Pike Winchester VA
Book a stay at this business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and a fitness center. Popular attractions R-C Track and Apple Blossom ...
8.6/10 Excellent! (554 reviews)
No issues

Reviewed on Feb 6, 2026

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Candlewood Suites Winchester by IHG
Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA

2.5 out of 5
1204 Berryville Avenue 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 in our reviews. ...
9.2/10 Wonderful! (863 reviews)
The staff was wonderful!

Reviewed on Jan 30, 2026

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Hampton Inn Winchester N/Conference Center, 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! (1,000 reviews)
Pet friendly and they provided a goodie bag for my dog - very welcoming.

Reviewed on Jan 13, 2026

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Hampton Inn Winchester-University/Mall Area
See all 2,075 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.