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Winchester

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Winchester Flights as Low as $47

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

Spirit Airlines
Tue, May 20 - Tue, May 27
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$47 Roundtrip, found 7 hours ago
$47
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Tue, May 20 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, May 27, priced at $47 found 7 hours ago
Frontier Airlines
Wed, Jun 11 - Wed, Jun 11
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$83 Roundtrip, found 7 hours ago
$83
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Wed, Jun 11 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Jun 11, priced at $83 found 7 hours ago
Frontier Airlines
Sat, Jul 5 - Sat, Jul 12
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$88 Roundtrip, found 7 hours ago
$88
Roundtrip
found 7 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 $88 found 7 hours ago
Spirit Airlines
Thu, May 29 - Sun, Jun 1
LAS
Harry Reid Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Thu, May 29 from Harry Reid Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Jun 1, priced at $119 found 1 day ago
Frontier Airlines
Tue, May 27 - Sun, Jun 1
LAS
Harry Reid Intl.
IAD
Washington Dulles Intl.
$137 Roundtrip, found 2 days ago
$137
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, May 27 from Harry Reid Intl. to Washington Dulles Intl., returning Sun, Jun 1, priced at $137 found 2 days ago
American Airlines
Thu, Jul 31 - Sun, Aug 3
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$157 Roundtrip, found 7 hours ago
$157
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Thu, Jul 31 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Sun, Aug 3, priced at $157 found 7 hours ago
Frontier Airlines
Mon, Jun 9 - Sat, Jun 14
BDL
Bradley Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$174 Roundtrip, found 15 hours ago
$174
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Mon, Jun 9 from Bradley Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Jun 14, priced at $174 found 15 hours ago
American Airlines
Thu, Jun 12 - Sun, Jun 15
BDL
Bradley Intl.
DCA
Ronald Reagan Washington National
$193 Roundtrip, found 15 hours ago
$193
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Thu, Jun 12 from Bradley Intl. to Ronald Reagan Washington National, returning Sun, Jun 15, priced at $193 found 15 hours ago
United
Thu, May 22 - Mon, May 26
BDL
Bradley Intl.
IAD
Washington Dulles Intl.
$193 Roundtrip, found 3 days ago
$193
Roundtrip
found 3 days ago
Select United flight, departing Thu, May 22 from Bradley Intl. to Washington Dulles Intl., returning Mon, May 26, priced at $193 found 3 days ago
Hawaiian Airlines
Tue, Jul 29 - Tue, Aug 5
LAS
Harry Reid Intl.
DCA
Ronald Reagan Washington National
$197 Roundtrip, found 5 days ago
$197
Roundtrip
found 5 days ago
Select Hawaiian Airlines flight, departing Tue, Jul 29 from Harry Reid Intl. to Ronald Reagan Washington National, returning Tue, Aug 5, priced at $197 found 5 days ago
Delta
Wed, Jun 18 - Tue, Jun 24
JAN
Evers Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$238 Roundtrip, just found
$238
Roundtrip
just found
Select Delta flight, departing Wed, Jun 18 from Evers Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Jun 24, priced at $238 just found
American Airlines
Tue, May 13 - Wed, May 14
JAN
Evers Intl.
DCA
Ronald Reagan Washington National
$352 Roundtrip, found 1 day ago
$352
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, May 13 from Evers Intl. to Ronald Reagan Washington National, returning Wed, May 14, priced at $352 found 1 day ago
Delta
Tue, May 13 - Wed, May 14
JAN
Evers Intl.
IAD
Washington Dulles Intl.
$361 Roundtrip, found 1 day ago
$361
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, May 13 from Evers Intl. to Washington Dulles Intl., returning Wed, May 14, priced at $361 found 1 day ago
Delta
Wed, May 14 - Mon, May 19
RAP
Rapid City Regional
BWI
Baltimore Washington Intl. Thurgood Marshall
$379 Roundtrip, found 15 hours ago
$379
Roundtrip
found 15 hours ago
Select Delta flight, departing Wed, May 14 from Rapid City Regional to Baltimore Washington Intl. Thurgood Marshall, returning Mon, May 19, priced at $379 found 15 hours ago
Delta
Tue, May 13 - Tue, May 13
RAP
Rapid City Regional
DCA
Ronald Reagan Washington National
$568 Roundtrip, found 13 hours ago
$568
Roundtrip
found 13 hours ago
Select Delta flight, departing Tue, May 13 from Rapid City Regional to Ronald Reagan Washington National, returning Tue, May 13, priced at $568 found 13 hours ago
United
Sat, May 10 - Mon, May 12
RAP
Rapid City Regional
IAD
Washington Dulles Intl.
$609 Roundtrip, found 15 hours ago
$609
Roundtrip
found 15 hours ago
Select United flight, departing Sat, May 10 from Rapid City Regional to Washington Dulles Intl., returning Mon, May 12, priced at $609 found 15 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 May, 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 $47, 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 $47 right now, why wait?

Winchester Flight Information
Destination airport
Baltimore Washington Intl. Thurgood Marshall
Destination airport IATA code
BWI
Roundtrip price
$47

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 $102 per night from May 11 to May 12
$102
includes taxes & fees
May 11 - May 12
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! (1,973 reviews)
"Friendly staff. Nice room. Great value"

Reviewed on May 1, 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 $100 per night from Jun 1 to Jun 2
$100
includes taxes & fees
Jun 1 - Jun 2
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! (1,010 reviews)
"Both check in and check out was great. Kevin was so kind checking us in at a late hour. It was a quiet and clean room. My husband slept so well and so late. We will definitely recommend and return this place in the future."

Reviewed on Apr 29, 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 $135 per night from May 11 to May 12
$135
includes taxes & fees
May 11 - May 12
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)
"Me and my daughters recently stayed 1 night to explore the Winchester area. We loved how close it was to the walking mall with all the shops and dining options. The girls really enjoyed the pool and hot tub - such a unique pool! The beds were super comfy, room very clean, staff very friendly. We ..."

Reviewed on Apr 28, 2025

The George Washington Hotel, A Wyndham Grand Hotel
Sleep Inn & Suites
Sleep Inn & Suites
2.5 out of 5
140 Costello Dr, Winchester, VA
The price is $78 per night from Jun 1 to Jun 2
$78
includes taxes & fees
Jun 1 - Jun 2
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! (1,001 reviews)
"great place"

Reviewed on Apr 30, 2025

Sleep Inn & Suites
Travelodge by Wyndham Winchester
Travelodge by Wyndham Winchester
2.5 out of 5
160 Front Royal Pike, Winchester, VA
The price is $70 per night from Jun 1 to Jun 2
$70
includes taxes & fees
Jun 1 - Jun 2
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! (1,104 reviews)
"Stayed for a night halfway through a 20 hour road trip. Very convenient location right off the highway. Lots of restaurants close by. Breakfast was good. Room was clean & comfortable."

Reviewed on Apr 30, 2025

Travelodge 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! (1,002 reviews)
"No issues"

Reviewed on Apr 29, 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
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 May 6 to May 7
$92
includes taxes & fees
May 6 - May 7
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! (1,207 reviews)
"Clean, well kept, well lit, staff friendly, Rocky very helpful"

Reviewed on May 1, 2025

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
The price is $72 per night from Jun 1 to Jun 2
$72
includes taxes & fees
Jun 1 - Jun 2
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! (1,000 reviews)
Recommend
"My go-to in Winchester Va Great stay!"

Reviewed on Apr 19, 2025

Red Roof Inn Winchester, VA
See all 1,981 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.