Title: Winchester Vacation Packages & Trips 2026 from CA $696 | 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. ![Beacon Hotel & Corporate Quarters](https://images.trvl-media.com/lodging/1000000/10000/7100/7069/0681397f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Beacon Hotel & Corporate Quarters Downtown Washington D.C. CA $696 per person Apr 11 - Apr 13 found 1 day ago Roundtrip flight included Toronto (YTZ) to Washington (DCA) 7.6/10 Good! (1,021 reviews) There wasn't a good smell in the hallway Reviewed on Mar 10, 2026 ![Residence Inn Alexandria Old Town South at Carlyle](https://images.trvl-media.com/lodging/3000000/2200000/2193300/2193207/64120e8a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Residence Inn Alexandria Old Town South at Carlyle Eisenhower East CA $979 per person May 1 - May 6 found 1 day ago Roundtrip flight included Toronto (YYZ) to Washington (DCA) 8.8/10 Excellent! (1,006 reviews) Room was spotless and everyone was absolutely a delight. There is NO SERVICE in the parking garage, which could be an issue in case of an emergency. The hotel is in a wonderful area close to the capital! Reviewed on Feb 26, 2026 ![Placemakr Buzzard Point](https://images.trvl-media.com/lodging/114000000/113170000/113163000/113162985/4d19de4c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Placemakr Buzzard Point Southwest CA $1,316 per person May 15 - May 18 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Washington (DCA) 9.2/10 Wonderful! (149 reviews) I loved my stay there. The staff was so nice and helpful. I would definitely stay again. Reviewed on Mar 5, 2026 ![Global Luxury Suites at Capitol Hill](https://images.trvl-media.com/lodging/84000000/83570000/83561700/83561623/3fabf963_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Global Luxury Suites at Capitol Hill Northeast CA $1,534 per person May 15 - May 18 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Washington (DCA) 8.2/10 Very Good! (808 reviews) Very nice accommodations in nice area of DC. The unit was exactly as described. Minor toilet issue but on site maintenance was readily accessible and available until 10:30pm each night. Reviewed on Mar 10, 2026 ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_6056879) ### Things to do in and around Winchester Winchester, Virginia, is perfect for outdoor enthusiasts and adventure seekers alike. Visitors can enjoy various recreational opportunities, including scenic hikes and golf vacations. The area also offers educational experiences and options for skiing during the winter months. Whether you're seeking a relaxing getaway or an active trip, Winchester provides a range of activities to suit every traveller's interests. **Shopping** In Winchester, you can shop at Apple Blossom Mall for a variety of stores and entertainment. Apple Valley Square Shopping Center offers local businesses in a family-friendly atmosphere. If you're up for a drive, explore Nalls Farm Market for fresh produce and unique gifts outside the city. **Recreation** [Jim Barnett Park](https://www.expedia.ca/Jim-Barnett-Park-Winchester.d6164028.Vacation-Attraction) offers a tranquil escape with its lush green spaces and scenic walking trails, perfect for relaxation. For a bit more activity, head to [Appleland Sports Center](https://www.expedia.ca/Appleland-Sports-Center-Stephens-City.d553248621587477489.Vacation-Attraction), where you can enjoy various recreational facilities. Rock Harbor Golf Course provides a delightful outdoor experience for golf enthusiasts. **Adventure** Experience the thrill of racing at Summit Point Motorsports Park, located 17.7km from Winchester, where adrenaline meets speed. For a fun-filled outdoor experience, head to Watermelon Park Campground, 20.9km away, perfect for family camping and adventure. Engage in an exhilarating paintball battle at North Mountain Paintball, also 17.7km from Winchester. **Nightlife** Winchester's nightlife features a vibrant atmosphere with an array of pubs and live music venues. Visit the Loudoun Street Grill for hearty meals and local brews, or enjoy live performances at the Bright Box Theater. Don't miss the laid-back vibe at the Alamo Drafthouse for a unique cinema experience. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Find the best attractions in Winchester Winchester, Virginia, is an excellent destination for outdoor and adventure enthusiasts, offering stunning scenery and a rich cultural experience. Explore historic houses and places, enjoy the beauty of local lakes, and discover popular attractions such as Winchester Cathedral. Whether you're seeking family-friendly activities or a deep dive into the area's history, Winchester has something for everyone. Don't miss out on the chance to experience the charm and allure of this vibrant city. - **Shenandoah University:** Experience the vibrant atmosphere of Shenandoah University, a historic college nestled in Winchester. With its beautiful campus and rich cultural vibes, it's an ideal spot for leisurely strolls and soaking in the academic spirit. - **Museum of the Shenandoah Valley:** This artistic gem showcases the region's rich history and culture through captivating exhibits and stunning gardens. The museum's engaging displays make it a delightful destination for art enthusiasts and history buffs alike. - **Shenandoah Valley Discovery Museum:** Perfect for families, this children's museum offers interactive exhibits that ignite curiosity and creativity in young minds. It's a fun-filled environment where learning meets play, making it a memorable stop for visitors of all ages. ### Best time to go to Winchester The best time to visit Winchester is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, 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 - Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Winchester. - Consider traveling to Winchester during the low season (January to March) for more affordable options. - 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 ![Holiday Inn Winchester Se-Historic Gateway by IHG](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/c68804b2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Winchester Se-Historic Gateway by IHG 333 Front Royal Pike Winchester VA Fully refundable CA $120 CA $134 total Mar 15 - Mar 16 includes taxes & fees 9/10 Wonderful! (1,000 reviews) very nice hotel,very clean Reviewed on Mar 7, 2026 [](https://expedia.ca/Hotel-Search?startDate=15%2F03%2F2026&endDate=16%2F03%2F2026&selected=1889084&PinnedHotelID=1889084&HadPinnedHotel=true®ionId=6056879) ![La Quinta Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/9e66afda_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 $145 CA $158 total Mar 12 - Mar 13 includes taxes & fees 9.2/10 Wonderful! (2,277 reviews) The hotel was conveniently located in town, even for a guest without a car on hand! Staff was AMAZING! Breakfast was solid and on time! Clean rooms and easy to navigate. Reviewed on Mar 8, 2026 [](https://expedia.ca/Hotel-Search?startDate=12%2F03%2F2026&endDate=13%2F03%2F2026&selected=2678524&PinnedHotelID=2678524&HadPinnedHotel=true®ionId=6056879) ![The George Washington Hotel, A Wyndham Grand Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5707228d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The George Washington Hotel, A Wyndham Grand Hotel 103 E Piccadilly St Winchester VA CA $166 CA $188 total Mar 17 - Mar 18 includes taxes & fees 9.4/10 Exceptional! (1,005 reviews) We stay here often on our travels between NC and NJ. The hotel is adjacent to Old Winchester which is a closed off road with many shops and restaurants. The hotel rooms are very comfortable. Reviewed on Mar 11, 2026 [](https://expedia.ca/Hotel-Search?startDate=17%2F03%2F2026&endDate=18%2F03%2F2026&selected=1364026&PinnedHotelID=1364026&HadPinnedHotel=true®ionId=6056879) [See all 2,046 properties in Winchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=12%2F03%2F2026&endDate=13%2F03%2F2026®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](https://images.trvl-media.com/place/6056879/c975fc72-ad57-4298-afc1-a46af23cbed9.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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) ### What to do in Winchester ![Shenandoah National Park Self-Driving Audio Tour](https://mediaim.expedia.com/localexpert/5064646/0663a437-1683-4a58-a7d2-c8231df55767.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Shenandoah Tour: Self-Guided Drive CA $23 per traveller **96%** of travellers recommend [](https://expedia.ca/things-to-do/shenandoah-tour-self-guided-drive.a5064646.activity-details) [See all activities in Winchester](https://expedia.ca/things-to-do/search?rid=6056879) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - [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) - 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[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) - 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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