Title: Winchester Vacation Packages & Trips 2026 from CA $822 | 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. ![The Melrose Georgetown Hotel](https://images.trvl-media.com/lodging/1000000/30000/23000/22903/bbc66681_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Melrose Georgetown Hotel Northwest CA $822 per person Mar 17 - Mar 20 found 16 hours ago Roundtrip flight included Toronto (YYZ) to Washington (DCA) 8.8/10 Excellent! (2,515 reviews) Staff is always the best Reviewed on Jan 23, 2026 ![Arlo Washington DC](https://images.trvl-media.com/lodging/107000000/106090000/106087200/106087178/8cf67881_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Arlo Washington DC Northwest CA $1,123 per person Mar 17 - Mar 20 found 16 hours ago Roundtrip flight included Toronto (YYZ) to Washington (DCA) 9.2/10 Wonderful! (1,093 reviews) Amazing staff and hotel room! We had a great time. Reviewed on Jan 24, 2026 ![Sofitel Washington DC Lafayette Square](https://images.trvl-media.com/lodging/1000000/860000/856600/856597/4877e6b4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sofitel Washington DC Lafayette Square Downtown Washington D.C. CA $1,832 per person Apr 6 - Apr 10 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Washington (DCA) 9/10 Wonderful! (1,084 reviews) Did not eat at the hotel. Reviewed on Jan 21, 2026 ![Tysons Corner Marriott](https://images.trvl-media.com/lodging/1000000/30000/23500/23487/0b8b0ac4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Tysons Corner Marriott CA $1,216 per person Apr 6 - Apr 10 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Washington (IAD) 9/10 Wonderful! (1,001 reviews) Very friendly staff and I especially appreciated how clean the room was and how the updates made an older hotel feel very fresh Reviewed on Jan 12, 2026 ![YOTEL Washington DC](https://images.trvl-media.com/lodging/1000000/20000/10600/10576/04246907_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### YOTEL Washington DC Northwest CA $870 per person Mar 17 - Mar 20 found 16 hours ago Roundtrip flight included Toronto (YYZ) to Washington (IAD) 8.2/10 Very Good! (2,262 reviews) Good location, comfortable room, good food. Reviewed on Jan 24, 2026 ### 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 ![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 $126 CA $137 total Jan 26 - Jan 27 includes taxes & fees 9.2/10 Wonderful! (2,248 reviews) Clean room. Friendly and helpful staff. Reviewed on Jan 21, 2026 [](https://expedia.ca/Hotel-Search?startDate=26%2F01%2F2026&endDate=27%2F01%2F2026&selected=2678524&PinnedHotelID=2678524&HadPinnedHotel=true®ionId=6056879) ![Microtel Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Microtel Inn & Suites by Wyndham Winchester 150 Faraday Plaza Winchester VA Fully refundableReserve now, pay when you stay CA $114 CA $124 total Feb 2 - Feb 3 includes taxes & fees 9/10 Wonderful! (1,438 reviews) Perfect for a single night, relatively clean, very friendly staff and decent breakfast. Reviewed on Jan 18, 2026 [](https://expedia.ca/Hotel-Search?startDate=02%2F02%2F2026&endDate=03%2F02%2F2026&selected=70921061&PinnedHotelID=70921061&HadPinnedHotel=true®ionId=6056879) ![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/9d44a9b1_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 $104 total Jan 26 - Jan 27 includes taxes & fees 8.4/10 Very Good! (1,066 reviews) Yes! Reviewed on Jan 18, 2026 [](https://expedia.ca/Hotel-Search?startDate=26%2F01%2F2026&endDate=27%2F01%2F2026&selected=9600&PinnedHotelID=9600&HadPinnedHotel=true®ionId=6056879) [See all 2,063 properties in Winchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=26%2F01%2F2026&endDate=27%2F01%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 top-notch restaurants or charming coffeehouses in this walkable area. 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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