Cheap Flights To Winchester 2026

Winchester Flights as Low as $90

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
Tue, Sep 29 - Tue, Oct 13
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$90
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Tue, Sep 29 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Oct 13, priced at $90 found 4 hours ago
Frontier Airlines
Frontier Airlines
Frontier Airlines
Southwest Airlines
Frontier Airlines
Frontier Airlines
Delta
Sat, Oct 3 - Tue, Oct 6
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$199
Roundtrip
just found
Select Delta flight, departing Sat, Oct 3 from Orlando Intl. to Ronald Reagan Washington National, returning Tue, Oct 6, priced at $199 just found
JetBlue Airways
American Airlines
Frontier Airlines
Sat, Aug 29 - Fri, Sep 11
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$209
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Aug 29 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Fri, Sep 11, priced at $209 found 1 day ago
Delta
Sat, Sep 5 - Mon, Sep 14
BDL
Bradley Intl.
DCA
Ronald Reagan Washington National
$238
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Sep 5 from Bradley Intl. to Ronald Reagan Washington National, returning Mon, Sep 14, priced at $238 found 1 day ago
JetBlue Airways
JetBlue Airways
Delta
Tue, Oct 20 - Tue, Oct 27
DAB
Daytona Beach Intl.
IAD
Washington Dulles Intl.
$343
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Oct 20 from Daytona Beach Intl. to Washington Dulles Intl., returning Tue, Oct 27, priced at $343 found 1 day ago
Delta
Tue, Oct 20 - Tue, Oct 27
DAB
Daytona Beach Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$357
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Oct 20 from Daytona Beach Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Oct 27, priced at $357 found 1 day ago

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
  • Car rentals
  • Flights
  • Waived booking fees on flights

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.