Title: Cheap Flights to Winchester , VA from CA $179 - Expedia.ca ![](https://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_flights_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Cheap Flights to Winchester , VA from CA $179 [View CA $179 flight on Fri, Oct 24, 2025](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YYC,to:DCA,departure:24/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:178.23&airProductToken=AQpkCjAIwYYBEgMzMTYYmBYgmF0o7pf7AjDemfsCOEdAAFgBagVCQVNJQ3IIR05BNUEyQkEKMAjBhgESBDg4MjEYmF0gQyiumvsCMJyb-wI4R0ABWAFqBUJBU0lDcghHTkE1QTJCQRIKCAEQARgBKgJBQxgBIgQIARABKAIoAygEMA0) - [Roundtrip](?flightType=roundtrip) - [One-way](?flightType=oneway) - [Multi-city](?flightType=multicity) ### Travellers Adults ChildrenAges 2 to 17 InfantsYounger than 2 EconomyPremium economyBusiness classFirst class Leaving from Going to Departing Returning Add a place to stay Add a car Direct flights only [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d6056879.Travel-Guide-Hotels)[Things to do in Winchester](https://expedia.ca/Things-To-Do-In-Winchester.d6056879.Travel-Guide-Activities)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d6056879.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d6056879.Destination-Travel-Guides) ## Popular airlines to Winchester - ![American Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Winchester, Virginia, United States of America,departure:09/10/2025TANYT&leg2=from:Winchester, Virginia, United States of America,to:CMH,departure:16/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![Delta](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Winchester, Virginia, United States of America,departure:09/10/2025TANYT&leg2=from:Winchester, Virginia, United States of America,to:CMH,departure:16/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![United](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Winchester, Virginia, United States of America,departure:09/10/2025TANYT&leg2=from:Winchester, Virginia, United States of America,to:CMH,departure:16/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![Southwest Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Winchester, Virginia, United States of America,departure:09/10/2025TANYT&leg2=from:Winchester, Virginia, United States of America,to:CMH,departure:16/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![Frontier Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg) Frontier Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Winchester, Virginia, United States of America,departure:09/10/2025TANYT&leg2=from:Winchester, Virginia, United States of America,to:CMH,departure:16/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![Alaska Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Winchester, Virginia, United States of America,departure:09/10/2025TANYT&leg2=from:Winchester, Virginia, United States of America,to:CMH,departure:16/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) - ![Spirit Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_NK.svg) Spirit Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Winchester, Virginia, United States of America,departure:09/10/2025TANYT&leg2=from:Winchester, Virginia, United States of America,to:CMH,departure:16/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"NK"}}]) ![notification illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__notification.svg) ### Be in the know Get alerts if flight prices drop or rise\* ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Book smarter Save up to 30% on select hotels after you book a flight\* ![trophy illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Earn twice Earn your airline miles on top of our rewards [Sign in](https://www.expedia.ca/login) ## How much is the cheapest flight to Winchester? Prices were available within the past 7 days and start at CA $179 for one-way flights and CA $300 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Thu, Oct 23 - Sat, Oct 25 YYC Calgary IAD Washington CA $300 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:IAD,departure:23/10/2025TANYT&leg2=from:IAD,to:YYC,departure:25/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:299.57&airProductToken=AQpDCiAI1YIBEgQxNjU1GJgWIK4cKP6R-wIw0pP7AjhOQABYAQofCNWCARIDMjEzGK4cIIgYKMyV-wIwxZb7AjhOQAFYAQpDCiAI1YIBEgQyNzQ4GIgYIK4cKNak-wIw2aX7AjhOQABYAQofCNWCARIDNzY0GK4cIJgWKJum-wIwgqj7AjhOQAFYARIKCAEQARgBKgJVQRgBIgQIARABKAQwAQ) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Wed, Oct 22 - Sat, Oct 25 YYC Calgary DCA Washington CA $300 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:DCA,departure:22/10/2025TANYT&leg2=from:DCA,to:YYC,departure:25/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:299.64&airProductToken=AQpkCjEIwYIBEgQyMzg5GJgWIK4cKJGH-wIw3oj7AjhCQABYAWoFQkFTSUNyCE9XQUNaTkJWCi8IwYIBEgM4ODgYrhwgQyivifsCMKeK-wI4QkABWAFqBUJBU0lDcghPV0FDWk5CVgplCjAIwYIBEgQyMzA0GEMgrhwo86T7AjD-pfsCOEJAAFgBagVCQVNJQ3IIT1dBQ1pOQlYKMQjBggESBDIzODkYrhwgmBYo2ab7AjC6qPsCOEJAAVgBagVCQVNJQ3IIT1dBQ1pOQlYSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Sat, Nov 8 - Mon, Nov 10 YYZ Toronto IAD Washington CA $318 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:IAD,departure:08/11/2025TANYT&leg2=from:IAD,to:YYZ,departure:10/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:317.89&airProductToken=AQo0CjIIwYYBEgQ4NjE2GJjOASCIGCi7yPwCMJbJ_AI4R0AAWAFqBUJBU0lDcghHTkEyQTlCQQpmCjEIwYYBEgQ4NzI2GIgYIJhdKNXa_AIwvtv8AjhHQABYAWoFQkFTSUNyCEdOQTJBOUJBCjEIwYYBEgM0MTUYmF0gmM4BKNTc_AIwst38AjhHQAFYAWoFQkFTSUNyCEdOQTJBOUJBEgoIAhABGAIqAkFDGAEiBAgBEAEoAigDKAQwAQ) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Wed, Oct 29 - Sun, Nov 9 YUL Montreal IAD Washington CA $402 Roundtrip found 19 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YUL,to:IAD,departure:29/10/2025TANYT&leg2=from:IAD,to:YUL,departure:09/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:401.87&airProductToken=AQpGCiEI0IgBEgQyNDcyGJhdIPjMASiE1fsCMNnV-wI4VkAAWAEKIQjQiAESBDI3MjMY-MwBIIgYKIHW-wIw2tb7AjhWQAFYAQpGCiEI0IgBEgQyNzIyGIgYIPjMASio0PwCMILR_AI4VkAAWAEKIQjQiAESBDI0NzMY-MwBIJhdKLnR_AIwhNL8AjhWQAFYARIKCAEQARgBKgJQRBgBIgQIARABKAQwAQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Tue, Oct 21 - Sat, Oct 25 YVR Vancouver IAD Washington CA $424 Roundtrip found 10 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:IAD,departure:21/10/2025TANYT&leg2=from:IAD,to:YVR,departure:25/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:423.54&airProductToken=AQpfCi4IwaYBEgM5MjYYuI0BIJIBKMD8-gIwg_36AjhYQABYAWoCU1ZyCEdIMk9YSkJOCi0IwaYBEgMzNDgYkgEgiBgo2P36AjCHgPsCOFhAAVgBagJTVnIIR0gyT1hKQk4KXwotCMGmARIDMzUxGIgYIJIBKNGk-wIwqKf7AjhYQABYAWoCU1ZyCEdIMk9YSkJOCi4IwaYBEgM5MjUYkgEguI0BKL-o-wIwhKn7AjhYQAFYAWoCU1ZyCEdIMk9YSkJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ## Find the cheapest month to fly from Columbus (CMH) to Washington (DCA) ### August is typically the cheapest month to fly From CA $136 - CA $498 per traveller. Expedia.ca gives you the best tools to secure great deals on flights to Winchester. Use our easy and convenient booking engine to browse nonstop flights and convenient departure points every day of the year. Search airfares from the top airlines to book your perfect flight to Winchester. Whatever your travel needs, you can always rely on Expedia.ca to help you find cheap flights to Winchester. Using our booking engine is simple - just type in your points of travel and preferred dates and Expedia.ca does the rest! If your travel times are flexible, you can find even better bargains by adjusting your flight dates. Browse connecting flights to increase your chances of finding even lower fares. Thanks to Expedia's Best Price Guarantee, you can book your Winchester flights with full confidence knowing that you've found the best deal online. Expedia.ca makes the booking process easy and stress-free by offering support along the entire way. Our friendly staff is available 24 hours a day to provide assistance and help you book your ticket. Call us toll-free at 1-888-397-3342 to answer any questions that you may have about your trip to Winchester. Looking to save even more? Get additional savings by bundling your Winchester flight with a hotel and/or car rental to create a bargain travel package. Early birds can discover terrific savings by booking in advance while last minute travelers can enjoy great last minute deals. With Expedia.ca, there's no shortage of options to save even more on your Winchester trip! Flights to Winchester information | Destination airport | Washington Dulles Intl. | | --- | --- | | Destination airport IATA code | IAD | | Destination city name | Washington | | Roundtrip price | CA $300 | ## Need more than a Flight to Winchester? Heading to Winchester? Explore Winchester with Expedia's Travel Guides to find the best hotels, vacation packages, car rental deals and more! [Winchester Hotels](https://expedia.ca/Winchester-Hotels.d6056879.Travel-Guide-Hotels)[Winchester Vacation Rentals](https://expedia.ca/Winchester-Vacation-Rentals.d6056879.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d6056879.Car-Rental-Guide)[Winchester Vacations](https://expedia.ca/Winchester.d6056879.Destination-Travel-Guides)[Things to do in Winchester](https://expedia.ca/Things-To-Do-In-Winchester.d6056879.Travel-Guide-Activities) ## Trending flights to Winchester Prices were available within the past 7 days and start at CA $179 for one-way flights and CA $300 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Thu, Oct 23 - Sat, Oct 25 YYC Calgary IAD Washington CA $300 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:IAD,departure:23/10/2025TANYT&leg2=from:IAD,to:YYC,departure:25/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:299.57&airProductToken=AQpDCiAI1YIBEgQxNjU1GJgWIK4cKP6R-wIw0pP7AjhOQABYAQofCNWCARIDMjEzGK4cIIgYKMyV-wIwxZb7AjhOQAFYAQpDCiAI1YIBEgQyNzQ4GIgYIK4cKNak-wIw2aX7AjhOQABYAQofCNWCARIDNzY0GK4cIJgWKJum-wIwgqj7AjhOQAFYARIKCAEQARgBKgJVQRgBIgQIARABKAQwAQ) ## Explore a world of travel with Expedia - Lodging - Flights - Packages ### Lodging - [3 Star Hotels in Old Town Winchester](https://www.expedia.ca/3Star-Old-Town-Winchester-Winchester-Hotels.s30-n6164092-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Stephens City](https://www.expedia.ca/4Star-Stephens-City-Hotels.s40-0-d12076.Travel-Guide-Filter-Hotels) - 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[Pet-Friendly Hotels in Old Town Winchester](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Pet-Friendly-Hotel.0-n6164092-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Old Town Winchester](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Spa-Hotel.0-n6164092-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Old Town Winchester Hotels](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels.0-n6164092-0.Travel-Guide-Filter-Hotels) - [Hotels near Patsy Cline Historic House](https://www.expedia.ca/Patsy-Cline-Historic-House-Hotels.0-l553248621532661841-0.Travel-Guide-Filter-Hotels) - [Hotels near Rock Harbor Golf Course](https://www.expedia.ca/Rock-Harbor-Golf-Course-Hotels.0-l553248621561864838-0.Travel-Guide-Filter-Hotels) - [Hotels near Shenandoah University](https://www.expedia.ca/Shenandoah-University-Hotels.0-l6127311-0.Travel-Guide-Filter-Hotels) - [B&B in Stephens City](https://www.expedia.ca/Stephens-City-Bed-And-Breakfast.d12076-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hotels & Resorts for Couples in Stephens City](https://www.expedia.ca/Stephens-City-Hotels-Couples-Resorts-Hotels.0-0-d12076-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Historic Hotels in Stephens City](https://www.expedia.ca/Stephens-City-Hotels-Historic-Hotel.0-0-d12076-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Stephens City](https://www.expedia.ca/Stephens-City-Hotels-Pet-Friendly-Hotel.0-0-d12076-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Stephens City Hotels](https://www.expedia.ca/Stephens-City-Hotels.d12076.Travel-Guide-Hotels) - [Hotels near Valerie Hill Winery](https://www.expedia.ca/Valerie-Hill-Winery-Hotels.0-l553248621532661834-0.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in White Post](https://www.expedia.ca/White-Post-Hotels-Honeymoon-Hotels.0-0-d184119-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [White Post Hotels](https://www.expedia.ca/White-Post-Hotels.d184119.Travel-Guide-Hotels) - [Hotels near Winchester-Frederick County Convention & Visitors Bureau](https://www.expedia.ca/Winchester-Frederick-County-Convention-Visitors-Bureau-Hotels.0-l553248621561864842-0.Travel-Guide-Filter-Hotels) - [Hotels with Bar in Winchester Historic District](https://www.expedia.ca/Winchester-Historic-District-Winchester-Hotels-Hotels-With-Bar.0-n918789051029594112-0-tHotelswithBar.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Winchester Historic District](https://www.expedia.ca/Winchester-Historic-District-Winchester-Hotels-Pet-Friendly-Hotel.0-n918789051029594112-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Winchester Historic District](https://www.expedia.ca/Winchester-Historic-District-Winchester-Hotels-Spa-Hotel.0-n918789051029594112-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Hotels near Winchester Medical Center](https://www.expedia.ca/Winchester-Medical-Center-Hotels.0-l6164057-0.Travel-Guide-Filter-Hotels) ### Flights - [Flights to Ashburn](https://www.expedia.ca/Cheap-Flights-To-Ashburn.d6035055.Travel-Guide-Flights) - [Flights to Banco](https://www.expedia.ca/Cheap-Flights-To-Banco.d3000355006.Travel-Guide-Flights) - [Flights to Blue Ridge](https://www.expedia.ca/Cheap-Flights-To-Blue-Ridge.d553248635976006713.Travel-Guide-Flights) - [Flights to Boston](https://www.expedia.ca/Cheap-Flights-To-Boston.d177514.Travel-Guide-Flights) - [Flights to Boyce](https://www.expedia.ca/Cheap-Flights-To-Boyce.d184084.Travel-Guide-Flights) - [Flights to Bristow](https://www.expedia.ca/Cheap-Flights-To-Bristow.d3000459833.Travel-Guide-Flights) - [Flights to Centreville](https://www.expedia.ca/Cheap-Flights-To-Centreville.d603264.Travel-Guide-Flights) - [Flights to Chantilly](https://www.expedia.ca/Cheap-Flights-To-Chantilly.d8638.Travel-Guide-Flights) - [Flights to Culpeper](https://www.expedia.ca/Cheap-Flights-To-Culpeper.d10640.Travel-Guide-Flights) - [Flights to Fairfax](https://www.expedia.ca/Cheap-Flights-To-Fairfax.d8062.Travel-Guide-Flights) - [Flights to Front Royal](https://www.expedia.ca/Cheap-Flights-To-Front-Royal.d7312.Travel-Guide-Flights) - [Flights to Gainesville](https://www.expedia.ca/Cheap-Flights-To-Gainesville.d6060136.Travel-Guide-Flights) - [Flights to Greenville](https://www.expedia.ca/Cheap-Flights-To-Greenville.d110800.Travel-Guide-Flights) - [Flights to Hamilton](https://www.expedia.ca/Cheap-Flights-To-Hamilton.d6319482.Travel-Guide-Flights) - [Flights to Herndon](https://www.expedia.ca/Cheap-Flights-To-Herndon.d7596.Travel-Guide-Flights) - [Flights to Leesburg](https://www.expedia.ca/Cheap-Flights-To-Leesburg.d8575.Travel-Guide-Flights) - [Flights to Luray](https://www.expedia.ca/Cheap-Flights-To-Luray.d6056892.Travel-Guide-Flights) - [Flights to Manassas](https://www.expedia.ca/Cheap-Flights-To-Manassas.d8779.Travel-Guide-Flights) - [Flights to Millwood](https://www.expedia.ca/Cheap-Flights-To-Millwood.d3000460156.Travel-Guide-Flights) - [Flights to New Market](https://www.expedia.ca/Cheap-Flights-To-New-Market.d9037.Travel-Guide-Flights) - [Flights to Nokesville](https://www.expedia.ca/Cheap-Flights-To-Nokesville.d6136847.Travel-Guide-Flights) - [Flights to Northern Virginia](https://www.expedia.ca/Cheap-Flights-To-Northern-Virginia.d6057018.Travel-Guide-Flights) - [Flights to Paris](https://www.expedia.ca/Cheap-Flights-To-Paris.d6050691.Travel-Guide-Flights) - [Flights to Reston](https://www.expedia.ca/Cheap-Flights-To-Reston.d10437.Travel-Guide-Flights) - [Flights to Skyland](https://www.expedia.ca/Cheap-Flights-To-Skyland.d3000008006.Travel-Guide-Flights) - [Flights to Stanley](https://www.expedia.ca/Cheap-Flights-To-Stanley.d184111.Travel-Guide-Flights) - [Flights to Sterling](https://www.expedia.ca/Cheap-Flights-To-Sterling.d9843.Travel-Guide-Flights) - [Flights to Syria](https://www.expedia.ca/Cheap-Flights-To-Syria.d184113.Travel-Guide-Flights) - [Flights to Warrenton](https://www.expedia.ca/Cheap-Flights-To-Warrenton.d7344.Travel-Guide-Flights) - [Flights to Washington Dulles Intl.](https://www.expedia.ca/Cheap-Flights-To-Washington-Dulles-Intl.d4473161.Travel-Guide-Flights) - [Flights from Winchester Regional](https://www.expedia.ca/lp/airports/wgo/flights-from-winchester-regional-airport) - [Flights from Clear Brook](https://www.expedia.ca/lp/flights/553248635975870250/flights-from-clear-brook) - [Flights from Blacksburg (BCB) to Winchester (WGO)](https://www.expedia.ca/lp/flights/bcb/wgo/blacksburg-to-winchester) - [Flights from Hartford (BDL) to Winchester (WGO)](https://www.expedia.ca/lp/flights/bdl/wgo/hartford-to-winchester) - [Flights from Baltimore (BWI) to Winchester (WGO)](https://www.expedia.ca/lp/flights/bwi/wgo/baltimore-to-winchester) - [Flights from Denver (DEN) to Winchester (WGO)](https://www.expedia.ca/lp/flights/den/wgo/denver-to-winchester) - [Flights from Dallas (DFW) to Winchester (WGO)](https://www.expedia.ca/lp/flights/dfw/wgo/dallas-to-winchester) - [Flights from El Paso (ELP) to Winchester (WGO)](https://www.expedia.ca/lp/flights/elp/wgo/el-paso-to-winchester) - [Flights from Fort Lauderdale (FLL) to Winchester (WGO)](https://www.expedia.ca/lp/flights/fll/wgo/fort-lauderdale-to-winchester) - [Flights from Greenville (GSP) to Winchester (WGO)](https://www.expedia.ca/lp/flights/gsp/wgo/greenville-to-winchester) - [Flights from Jacksonville (JAX) to Winchester (WGO)](https://www.expedia.ca/lp/flights/jax/wgo/jacksonville-to-winchester) - [Flights from Melbourne (MEL) to Winchester (WGO)](https://www.expedia.ca/lp/flights/mel/wgo/melbourne-to-winchester) - [Flights from Sarasota (SRQ) to Winchester (WGO)](https://www.expedia.ca/lp/flights/srq/wgo/sarasota-to-winchester) - [Flights from Syracuse (SYR) to Winchester (WGO)](https://www.expedia.ca/lp/flights/syr/wgo/syracuse-to-winchester) - [Flights from Calgary (YYC) to Winchester (WGO)](https://www.expedia.ca/lp/flights/yyc/wgo/calgary-to-winchester) - [Flights from Toronto (YYZ) to Winchester (WGO)](https://www.expedia.ca/lp/flights/yyz/wgo/toronto-to-winchester) ### Packages - [Appleland Sports Center](https://www.expedia.ca/Appleland-Sports-Center-Stephens-City.d553248621587477489.Vacation-Attraction) - [Jim Barnett Park](https://www.expedia.ca/Jim-Barnett-Park-Winchester.d6164028.Vacation-Attraction) \*Available to Expedia members.