Cheap Flights To Winchester 2025

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Winchester Flights as Low as $201

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.

Delta
Tue, Jun 3 - Tue, Jun 10
CHS
Charleston Intl.
IAD
Washington Dulles Intl.
$201 Roundtrip, found 3 days ago
$201
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Jun 3 from Charleston Intl. to Washington Dulles Intl., returning Tue, Jun 10, priced at $201 found 3 days ago
Spirit Airlines
Sun, May 25 - Wed, May 28
CHS
Charleston Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$224 Roundtrip, found 4 days ago
$224
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Sun, May 25 from Charleston Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, May 28, priced at $224 found 4 days ago
United
Sat, May 24 - Tue, May 27
CMH
John Glenn Columbus Intl.
IAD
Washington Dulles Intl.
$228 Roundtrip, found 1 day ago
$228
Roundtrip
found 1 day ago
Select United flight, departing Sat, May 24 from John Glenn Columbus Intl. to Washington Dulles Intl., returning Tue, May 27, priced at $228 found 1 day ago
American Airlines
Sun, May 25 - Wed, May 28
CHS
Charleston Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$237 Roundtrip, found 4 days ago
$237
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sun, May 25 from Charleston Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, May 28, priced at $237 found 4 days ago
Delta
Fri, May 9 - Thu, May 15
HSV
Huntsville Intl.
DCA
Ronald Reagan Washington National
$279 Roundtrip, found 1 day ago
$279
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, May 9 from Huntsville Intl. to Ronald Reagan Washington National, returning Thu, May 15, priced at $279 found 1 day ago
United
Fri, May 9 - Sun, May 11
HSV
Huntsville Intl.
IAD
Washington Dulles Intl.
$289 Roundtrip, found 1 day ago
$289
Roundtrip
found 1 day ago
Select United flight, departing Fri, May 9 from Huntsville Intl. to Washington Dulles Intl., returning Sun, May 11, priced at $289 found 1 day ago
American Airlines
Fri, May 9 - Sun, May 11
HSV
Huntsville Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$309 Roundtrip, found 1 day ago
$309
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, May 9 from Huntsville Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, May 11, priced at $309 found 1 day ago
Hawaiian Airlines
Tue, Sep 9 - Tue, Sep 23
STS
Sonoma County
BWI
Baltimore Washington Intl. Thurgood Marshall
$361 Roundtrip, found 22 hours ago
$361
Roundtrip
found 22 hours ago
Select Hawaiian Airlines flight, departing Tue, Sep 9 from Sonoma County to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Sep 23, priced at $361 found 22 hours ago
Hawaiian Airlines
Mon, Sep 8 - Sat, Sep 20
STS
Sonoma County
IAD
Washington Dulles Intl.
$406 Roundtrip, found 22 hours ago
$406
Roundtrip
found 22 hours ago
Select Hawaiian Airlines flight, departing Mon, Sep 8 from Sonoma County to Washington Dulles Intl., returning Sat, Sep 20, priced at $406 found 22 hours ago
Alaska Airlines
Wed, Sep 10 - Mon, Sep 22
STS
Sonoma County
IAD
Washington Dulles Intl.
$467 Roundtrip, found 22 hours ago
$467
Roundtrip
found 22 hours ago
Select Alaska Airlines flight, departing Wed, Sep 10 from Sonoma County to Washington Dulles Intl., returning Mon, Sep 22, priced at $467 found 22 hours ago
Alaska Airlines
Wed, Sep 10 - Mon, Sep 22
STS
Sonoma County
DCA
Ronald Reagan Washington National
$472 Roundtrip, found 22 hours ago
$472
Roundtrip
found 22 hours ago
Select Alaska Airlines flight, departing Wed, Sep 10 from Sonoma County to Ronald Reagan Washington National, returning Mon, Sep 22, priced at $472 found 22 hours ago
American Airlines
Sun, May 4 - Sun, May 11
CHS
Charleston Intl.
DCA
Ronald Reagan Washington National
$568 Roundtrip, found 5 days ago
$568
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sun, May 4 from Charleston Intl. to Ronald Reagan Washington National, returning Sun, May 11, priced at $568 found 5 days ago
United
Mon, Sep 22 - Mon, Oct 13
CEB
Mactan - Cebu Intl.
IAD
Washington Dulles Intl.
$874 Roundtrip, found 1 day ago
$874
Roundtrip
found 1 day ago
Select United flight, departing Mon, Sep 22 from Mactan - Cebu Intl. to Washington Dulles Intl., returning Mon, Oct 13, priced at $874 found 1 day ago
Philippine Airlines
Mon, Sep 22 - Mon, Oct 13
CEB
Mactan - Cebu Intl.
DCA
Ronald Reagan Washington National
$943 Roundtrip, found 1 day ago
$943
Roundtrip
found 1 day ago
Select Philippine Airlines flight, departing Mon, Sep 22 from Mactan - Cebu Intl. to Ronald Reagan Washington National, returning Mon, Oct 13, priced at $943 found 1 day ago
EVA Airways
Mon, Sep 22 - Tue, Oct 14
CEB
Mactan - Cebu Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$1,056 Roundtrip, found 1 day ago
$1,056
Roundtrip
found 1 day ago
Select EVA Airways flight, departing Mon, Sep 22 from Mactan - Cebu Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Oct 14, priced at $1,056 found 1 day ago
Qatar Airways
Mon, Sep 22 - Tue, Oct 14
CEB
Mactan - Cebu Intl.
IAD
Washington Dulles Intl.
$1,440 Roundtrip, found 1 day ago
$1,440
Roundtrip
found 1 day ago
Select Qatar Airways flight, departing Mon, Sep 22 from Mactan - Cebu Intl. to Washington Dulles Intl., returning Tue, Oct 14, priced at $1,440 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
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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.