Cheap Flights To Winchester 2026

Winchester Flights as Low as $71

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Frontier Airlines
Wed, Nov 18 - Tue, Dec 1
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$76
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, Nov 18 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Dec 1, priced at $76 found 5 days ago
Frontier Airlines
Sat, Dec 5 - Fri, Dec 11
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$108
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Dec 5 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Fri, Dec 11, priced at $108 found 4 days ago
Frontier Airlines
Delta
Tue, Nov 17 - Wed, Dec 2
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$137
Roundtrip
found 16 hours ago
Select Delta flight, departing Tue, Nov 17 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Wed, Dec 2, priced at $137 found 16 hours ago
Frontier Airlines
Mon, Nov 2 - Wed, Nov 4
RDU
Raleigh - Durham Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$143
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Mon, Nov 2 from Raleigh - Durham Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Nov 4, priced at $143 found 23 hours ago
United
Wed, Dec 16 - Mon, Dec 21
RDU
Raleigh - Durham Intl.
IAD
Washington Dulles Intl.
$157
Roundtrip
found 3 days ago
Select United flight, departing Wed, Dec 16 from Raleigh - Durham Intl. to Washington Dulles Intl., returning Mon, Dec 21, priced at $157 found 3 days ago
United
Sat, Nov 14 - Sun, Nov 15
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$157
Roundtrip
found 7 hours ago
Select United flight, departing Sat, Nov 14 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Sun, Nov 15, priced at $157 found 7 hours ago
American Airlines
Thu, Dec 10 - Mon, Dec 14
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$169
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Thu, Dec 10 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Mon, Dec 14, priced at $169 found 2 hours ago
Southwest Airlines
Thu, Dec 10 - Mon, Dec 14
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$169
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Thu, Dec 10 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Mon, Dec 14, priced at $169 found 2 hours ago
Delta
Tue, Nov 24 - Mon, Nov 30
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$172
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Nov 24 from Orlando Intl. to Ronald Reagan Washington National, returning Mon, Nov 30, priced at $172 found 6 days ago
Frontier Airlines
Southwest Airlines
Delta
Wed, Nov 4 - Mon, Nov 9
SBA
Santa Barbara Municipal
BWI
Baltimore Washington Intl. Thurgood Marshall
$377
Roundtrip
found 11 hours ago
Select Delta flight, departing Wed, Nov 4 from Santa Barbara Municipal to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Nov 9, priced at $377 found 11 hours ago
Delta
Southwest Airlines

Flights to

If is calling your name, then book your next flight to (airport). And with the AARP Travel Center Powered by Expedia®, this trip isn't too far out of reach. With the best rates from Expedia combined with members-only discounts, AARP Travel offers members the best price in travel, guaranteed.

AARP members get exclusive rates on:

  • Hotels
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  • Flights
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Whether it's a weekend getaway, tropical vacation, backpacking adventure, ski escape or another trip you're dreaming of, we'll help you get there (without breaking the bank).

Transportation at the Airport

Once you have reserved plane tickets to , you may want to book a car so you can get around on your own. You can request car rentals under our cars tab and hop into the driver's seat as soon as you step outside. For more information, check out the Winchester (and vicinity) Car Rentals Guide.

Things to Do in

Not sure where to start? Not to worry—there's plenty to do in this city. No matter what you decide to do with your time, you're sure to have fun in this city.

If you're looking for some fun activities to do in , make sure you look at our "Things to Do in Winchester (and vicinity)" page for excursions and activities for the whole clan.

Book Your Hotel in

has hotel to choose from, make sure you check out our hotel listings tab for some great recommendations from past visitors. No matter where you stay, just remember that you'll get the best price out there when you stay with AARP Travel.

Booking Your Flight

Once you have planned your travel dates, allow us here at AARP Travel to connect you with inexpensive tickets to . Do not wait a moment longer—book your airfare today and land in tomorrow.