Title: Winchester Vacation Packages & Trips 2025/2026 from CA $814 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d6056879.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d6056879.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.ca/Cheap-Flights-To-Winchester.d6056879.Travel-Guide-Flights)[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) ![](https://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Winchester Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence ### Better together Save up to CA $1,096 when you book a flight and hotel together\* ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package ### Rest easy Plan, book, and manage your trip all in one place #### Your Winchester Vacation The rich history and small-town feel are just the start of the things Winchester has on offer. Experience the best of this city your way with a tailor-made Winchester vacation package. You'll want to do some exploring during your trip to Winchester. Find time for big-name attractions such as [Shenandoah University](https://www.expedia.ca/Shenandoah-University-Winchester.d6127311.Vacation-Attraction), [Museum of the Shenandoah Valley](https://www.expedia.ca/Museum-Of-The-Shenandoah-Valley-Winchester.d6127313.Vacation-Attraction) and [Apple Blossom Mall](https://www.expedia.ca/Apple-Blossom-Mall-Winchester.d6164018.Vacation-Attraction). Whatever your travel plans or the size of your budget, organizing your ultimate tailored Winchester vacation is easy with Expedia. ## Top Winchester Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Lyle Washington D.C.](https://images.trvl-media.com/lodging/1000000/10000/6700/6619/e9a034ed_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Lyle Washington D.C. Northwest CA $814 per person Nov 12 - Nov 15 found 8 hours ago Roundtrip flight included Toronto (YYZ) to Washington (DCA) 9.4/10 Exceptional! (1,540 reviews) Very comfortable rooms. Helpful staff. Reviewed on Oct 6, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-12/2025-11-15/?FromAirport=YYZ&Destination=DCA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=6619&paandie=true&dealMarker=eO70H6xPmfaeB10sPf0jdnUj7oNmN72jNSltfhgNMZ2LsxOvqLgLN2FIungmc6ur) ![Sagamore Pendry Baltimore](https://images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/45fde7f6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sagamore Pendry Baltimore Fells Point CA $1,161 per person Nov 13 - Nov 16 found 1 day ago Roundtrip flight included Toronto (YYZ) to Baltimore (BWI) 9.4/10 Exceptional! (1,002 reviews) We paid an upgrade with balcony but you cannot use it because the waterfront is so smelly. You do not want to sit outside. The hotel is nice but so NOISY. It is a very young area with lost of partying and limited nicer restaurants around. We got woken up at midnight 3:00am and 5:30 am by partners screaming. NO thank you The hotel breakfast was the worse salmon Florentine, it tasted like vineger. I didn't,t even eat my salad. 77$ for 7 breakfast was a waste. Reviewed on Oct 6, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-13/2025-11-16/?FromAirport=YYZ&Destination=BWI&NumRoom=1&NumAdult=2&NumChild=0&hotelId=17395897&paandie=true&dealMarker=73w_BNPqGYLQRy9HgIHmh198L3O3ts1uk6qU19WpMVsX53ELmhQZiqnopQh_VjFB) ![Rosewood Washington, D.C.](https://images.trvl-media.com/lodging/6000000/5490000/5487000/5486908/760b0e05_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Rosewood Washington, D.C. Georgetown CA $1,766 per person Nov 13 - Nov 16 found 1 day ago Roundtrip flight included Toronto (YYZ) to Washington (DCA) 9.2/10 Wonderful! (191 reviews) I want to move in! Perfect location and property for picky guests! Staff was incredible. The restaurant was amazing and beautiful. Try the giant shrimp cocktail! I wish I had time to enjoy the rooftop pool. Reviewed on Sep 26, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-13/2025-11-16/?FromAirport=YYZ&Destination=DCA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=5486908&paandie=true&dealMarker=73w_BNPqGYLQRy9HgIHmh198L3O3ts1uk6qU19WpMVtKEKWMoYpcuEssqLvxIENA) ![Sheraton Baltimore North Hotel](https://images.trvl-media.com/lodging/1000000/20000/13900/13890/dc4fe95a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sheraton Baltimore North Hotel CA $986 per person Nov 18 - Nov 23 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Baltimore (BWI) 8.2/10 Very Good! (1,002 reviews) Easy parking and quiet area. Reviewed on Sep 30, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-18/2025-11-23/?FromAirport=YYZ&Destination=BWI&NumRoom=1&NumAdult=2&NumChild=0&hotelId=13890&paandie=true&dealMarker=f7ItZE713fY5k-vqiJsZn6lJFr0_gu2x88WyTeFl2WvtSUWK4KOdbmJlfG98blaJ) ![Comfort Suites Columbia Gateway](https://images.trvl-media.com/lodging/2000000/1160000/1155100/1155026/37cd357c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Comfort Suites Columbia Gateway CA $1,089 per person Nov 18 - Nov 23 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Baltimore (BWI) 8.2/10 Very Good! (1,004 reviews) The lobby smelled like dirty mop. The parking lot is very small and can’t accommodate guest parking at night (after 11pm). The rooms lighting was extremely dim. Reviewed on Oct 5, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-18/2025-11-23/?FromAirport=YYZ&Destination=BWI&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1155026&paandie=true&dealMarker=o-VptUOyo6Gfx1un066UMFcLARGLITSE7QiXA_V5Xq7ExpDzmGhrPRPm97fOkmh-) ### Things to do in and around Winchester Winchester, Virginia, is perfect for outdoor enthusiasts and adventure seekers alike, offering a range of activities such as golfing, skiing, and various recreation opportunities. Visitors can explore scenic landscapes and engage in exciting shore excursions, making it an ideal spot for memorable Winchester trips. Whether you're looking for a relaxing getaway or an action-packed adventure, Winchester has something to suit every traveller's taste. **Shopping** For a delightful shopping experience in Winchester, visit [Apple Blossom Mall](https://www.expedia.ca/Apple-Blossom-Mall.d6164018.Vacation-Attraction) for a variety of stores and entertainment. [Nalls Farm Market](https://www.expedia.ca/Nalls-Farm-Market.d553248621532661846.Vacation-Attraction) offers local goods, while Apple Valley Square Shopping Center combines business and family vibes. If you're up for a drive, explore nearby shopping options for even more choices. **Recreation** Enjoy a round of golf at [Rock Harbor Golf Course](https://www.expedia.ca/Rock-Harbor-Golf-Course.d553248621561864838.Vacation-Attraction), where you can embrace the outdoor vibes amidst beautiful landscapes. For relaxation, visit [Jim Barnett Park](https://www.expedia.ca/Jim-Barnett-Park.d6164028.Vacation-Attraction), perfect for unwinding in nature. Don't miss a show at [Bright Box Theater](https://www.expedia.ca/Bright-Box-Theater.d553248621561864843.Vacation-Attraction), offering a charming atmosphere for culture and family entertainment. **Adventure** [Summit Point Motorsports Park](https://www.expedia.ca/Summit-Point-Motorsports-Park.d6164103.Vacation-Attraction) offers thrilling motor racing experiences, located 17.7km from Winchester, perfect for adrenaline seekers. For a family-friendly adventure, [Watermelon Park Campground](https://www.expedia.ca/Watermelon-Park-Campground.d553248621532661928.Vacation-Attraction), 20.9km away, provides an outdoor haven. [Tuckers Lane Trailhead](https://www.expedia.ca/Tuckers-Lane-Trailhead.d553248633992585760.Vacation-Attraction), 32.2km from town, invites hikers to explore scenic trails amidst nature. **Nightlife** Winchester offers a charming nightlife with venues like the vibrant Loudoun Street, perfect for a casual stroll. Try the lively atmosphere at the recently renovated 50/50 Taphouse or enjoy live music at the Bright Box Theater for a delightful evening out. *\*Distances are measured in a straight line; actual driving distances may vary depending on the route.* ### Find the best attractions in Winchester Winchester, Virginia, offers a delightful blend of outdoor adventures and rich history, making it perfect for family-friendly vacations. Explore historic houses and scenic lakes, and immerse yourself in the local culture at various attractions. Whether you're interested in discovering Winchester's storied past or enjoying its beautiful landscapes, there's something for everyone. Don't miss out on the popular attractions and resorts in the area to enhance your visit. - **[Shenandoah University:](https://www.expedia.ca/Shenandoah-University.d6127311.Vacation-Attraction)** Immerse yourself in the vibrant atmosphere of Shenandoah University, a historic institution that showcases the rich educational culture of Winchester. Explore its charming campus, filled with local art and events that reflect the community's spirit. - **[Museum of the Shenandoah Valley:](https://www.expedia.ca/Museum-Of-The-Shenandoah-Valley.d6127313.Vacation-Attraction)** Experience a captivating blend of art and history at the Museum of the Shenandoah Valley. This art museum features stunning exhibitions that highlight the region's cultural heritage, making it a perfect spot for art enthusiasts. - **[Shenandoah Valley Discovery Museum:](https://www.expedia.ca/Shenandoah-Valley-Discovery-Museum.d553248621587527659.Vacation-Attraction)** Delight in family-friendly fun at the Shenandoah Valley Discovery Museum, designed for children. Engage in interactive exhibits that inspire curiosity and learning, fostering a love for exploration in young minds. ### Best time to go to Winchester The best time to visit Winchester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Winchester falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Winchester falls in January, visitor numbers are slightly low and weather is mostly sunny with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | --- | --- | --- | --- | --- | --- | | January | 31.3°F (-0.4°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | February | 34.7°F (1.5°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | March | 42.3°F (5.7°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | April | 52.9°F (11.6°C) | Light Rain | Mostly Sunny | Average | Average | | May | 62.4°F (16.9°C) | Light Rain | Mostly Sunny | Average | Slightly High | | June | 70.9°F (21.6°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | July | 75.9°F (24.4°C) | Light Rain | Mostly Sunny | Slightly High | Average | | August | 73.8°F (23.2°C) | Light Rain | Mostly Sunny | Average | Average | | September | 66.9°F (19.4°C) | Light Rain | Mostly Sunny | Average | Average | | October | 55.8°F (13.2°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | November | 43.5°F (6.4°C) | Light Rain | Mostly Sunny | Average | Average | | December | 36.7°F (2.6°C) | Light Rain | Mostly Sunny | Slightly Low | Average | ### Tips to save on your trip to Winchester - Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings. - Consider traveling during the off-peak season (typically January to March) for more affordable package holidays to Winchester. - Use the *Price per traveler* filter on Expedia to find a package deal that suits your budget. - Check the *VIP Access properties* filter to discover outstanding hotels with added member perks at select properties. ## Ready to book your vacation to Winchester? Choose your dates ## Winchester Hotel Deals ![Hampton Inn Winchester-University/Mall Area](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn Winchester-University/Mall Area 640 East Jubal Early Drive, Winchester, VA Fully refundableReserve now, pay when you stay CA $148 CA $168 total Nov 2 - Nov 3 includes taxes & fees 9/10 Wonderful! (1,007 reviews) "Gym did not have disinfecting wipes to use in the equipment but otherwise great!" Reviewed on Oct 4, 2025 [](https://expedia.ca/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=19971&PinnedHotelID=19971&HadPinnedHotel=true®ionId=6056879) ![La Quinta Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### La Quinta Inn & Suites by Wyndham Winchester 1055 Millwood Pike, Route 50 East, Winchester, VA Fully refundableReserve now, pay when you stay CA $143 CA $156 total Oct 29 - Oct 30 includes taxes & fees 9.2/10 Wonderful! (2,171 reviews) "Great location." Reviewed on Oct 6, 2025 [](https://expedia.ca/Hotel-Search?startDate=29%2F10%2F2025&endDate=30%2F10%2F2025&selected=2678524&PinnedHotelID=2678524&HadPinnedHotel=true®ionId=6056879) ![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/28616e5b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Travelodge by Wyndham Winchester 160 Front Royal Pike, Winchester, VA Fully refundableReserve now, pay when you stay CA $96 CA $105 total Oct 29 - Oct 30 includes taxes & fees 8.4/10 Very Good! (1,073 reviews) "Excellent staff" Reviewed on Oct 4, 2025 [](https://expedia.ca/Hotel-Search?startDate=29%2F10%2F2025&endDate=30%2F10%2F2025&selected=9600&PinnedHotelID=9600&HadPinnedHotel=true®ionId=6056879) [See all 2,018 properties in Winchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=11%2F10%2F2025&endDate=12%2F10%2F2025®ionId=6056879) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Discover the most popular places to visit in Winchester #### Jim Barnett Park Explore the great outdoors at Jim Barnett Park, a lovely green space in Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area. [](https://expedia.ca/Jim-Barnett-Park-Winchester.d6164028.Vacation-Attraction) ## 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) - [Hotels near Apple Blossom Mall](https://www.expedia.ca/Apple-Blossom-Mall-Hotels.0-l6164018-0.Travel-Guide-Filter-Hotels) - [Apartments in Boyce](https://www.expedia.ca/Boyce-Apartments.d184084-aaApartments.Travel-Guide-Accommodation) - [B&B in Boyce](https://www.expedia.ca/Boyce-Bed-And-Breakfast.d184084-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Boutique Hotels in Boyce](https://www.expedia.ca/Boyce-Hotels-Boutique-Hotel.0-0-d184084-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Boyce Hotels](https://www.expedia.ca/Boyce-Hotels.d184084.Travel-Guide-Hotels) - 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[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 Boyce](https://www.expedia.ca/Cheap-Flights-To-Boyce.d184084.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) - [Banco Vacations](https://www.expedia.ca/Banco.d3000355006.Destination-Travel-Guides) - [Ben Lomond Manor House & Old Rose Garden](https://www.expedia.ca/Ben-Lomond-Manor-House-Old-Rose-Garden-Manassas.d553248621532661892.Vacation-Attraction) - [Blue Ridge Vacations](https://www.expedia.ca/Blue-Ridge.d553248635976006713.Destination-Travel-Guides) - [Bryce Ski Resort](https://www.expedia.ca/Bryce-Ski-Resort-Mount-Jackson.d6219474.Vacation-Attraction) - [Cana Vineyards and Winery](https://www.expedia.ca/Cana-Vineyards-And-Winery-Middleburg.d553248621532661900.Vacation-Attraction) - [Dulles Town Center](https://www.expedia.ca/Dulles-Town-Center-Sterling.d553248621560871589.Vacation-Attraction) - [Elizabeth Mills Riverfront Park and Kephart Bridge Landing](https://www.expedia.ca/Elizabeth-Mills-Riverfront-Park-And-Kephart-Bridge-Landing-Leesburg.d553248621532662016.Vacation-Attraction) - [Front Royal Entrance Shenandoah National Park](https://www.expedia.ca/Front-Royal-Entrance-Shenandoah-National-Park-Front-Royal.d6129961.Vacation-Attraction) - [Jim Barnett Park](https://www.expedia.ca/Jim-Barnett-Park-Winchester.d6164028.Vacation-Attraction) - [Luray Caverns](https://www.expedia.ca/Luray-Caverns-Luray.d6093221.Vacation-Attraction) - [Manassas Vacations](https://www.expedia.ca/Manassas.d8779.Destination-Travel-Guides) - [Mary's Rock Summit Trailhead](https://www.expedia.ca/Marys-Rock-Summit-Trailhead-Luray.d553248621532661700.Vacation-Attraction) - [Naked Mountain Winery & Vineyards](https://www.expedia.ca/Naked-Mountain-Winery-Vineyards-Delaplane.d553248621532661859.Vacation-Attraction) - [National Conference Center](https://www.expedia.ca/National-Conference-Center-Leesburg.d6249239.Vacation-Attraction) - [National Firearms Museum](https://www.expedia.ca/National-Firearms-Museum-Fairfax.d6083577.Vacation-Attraction) - [New Market Vacations](https://www.expedia.ca/New-Market.d9037.Destination-Travel-Guides) - [Northern Virginia Vacations](https://www.expedia.ca/Northern-Virginia.d6057018.Destination-Travel-Guides) - [Old Jail Museum](https://www.expedia.ca/Old-Jail-Museum-Warrenton.d6212070.Vacation-Attraction) - [Potomac Crossing Park](https://www.expedia.ca/Potomac-Crossing-Park-Leesburg.d553248621532662004.Vacation-Attraction) - [Rose River Falls](https://www.expedia.ca/Rose-River-Falls-Syria.d553248621587527634.Vacation-Attraction) - [Round Hill Vacations](https://www.expedia.ca/Round-Hill.d3000460647.Destination-Travel-Guides) - [Skyland Vacations](https://www.expedia.ca/Skyland.d3000008006.Destination-Travel-Guides) - [Skyline Caverns](https://www.expedia.ca/Skyline-Caverns-Front-Royal.d6093201.Vacation-Attraction) - [Splash Down Water Park](https://www.expedia.ca/Splash-Down-Water-Park-Manassas.d6093231.Vacation-Attraction) - [Stanley Vacations](https://www.expedia.ca/Stanley.d184111.Destination-Travel-Guides) - [Sterling Vacations](https://www.expedia.ca/Sterling.d9843.Destination-Travel-Guides) - [Steven F. Udvar-Hazy Center](https://www.expedia.ca/Steven-F-Udvar-Hazy-Center-Chantilly.d6083575.Vacation-Attraction) - [Syria Vacations](https://www.expedia.ca/Syria.d184113.Destination-Travel-Guides) - [Wisteria Farm and Vineyard](https://www.expedia.ca/Wisteria-Farm-And-Vineyard-Stanley.d553248621532661739.Vacation-Attraction) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)