Title: Visit Winchester: Best of Winchester Tourism | Expedia Travel Guide - 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)[Winchester Vacation Packages](https://expedia.ca/Winchester.d6056879.Destination-Travel-Guides) # Winchester ## Travel Guide ![Winchester](https://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![MAY 9, 2023 - WINCHESTER, KENTUCKY - aerial view of historic small town of Winchester with Town Clocktower and historic storefronts and buildings](https://images.trvl-media.com/place/6056879/31f89911-167f-41d8-88d6-62f9fb8763d2.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Handley Library ](https://images.trvl-media.com/place/6056879/dd3561a1-54d7-46cf-9e70-15a3b654b5eb.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Gardens at Glen Burnie House.](https://images.trvl-media.com/place/6056879/a8b6bc61-16a0-4bd7-8e9c-ba5025791cbb.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![A nice 3 block outdoor downtown shopping area with dining and bars also. ](https://images.trvl-media.com/place/6056879/3acc501a-a330-4063-b538-b2368ef6a4c5.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## Visit Winchester Where to stay Things to do ### Where to stay in Winchester ![The Courthouse in Winchester, Virginia.](https://images.trvl-media.com/place/6164092/74e89cff-4502-4b70-84ac-0bb3e6917b82.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Old Town Winchester Old Town Winchester is known for its ample dining options, and you can make a stop by Bright Box Theater and Shenandoah Valley Discovery Museum while in the area. [](https://expedia.ca/Winchester-Old-Town-Winchester.dx6164092) ![Buildings and streets in the historic part of the ancient city of Winchester in Virginia.](https://images.trvl-media.com/place/918789051029594112/06c2fe17-e2c5-4e1c-941c-f181c2f40c91.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Winchester Historic District While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Shenandoah Valley Discovery Museum. [](https://expedia.ca/Winchester-Winchester-Historic-District.dx918789051029594112) - Winchester Hotel Deals - Vacation Rentals in Winchester ![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 CA $107 CA $121 total Apr 5 - Apr 6 includes taxes & fees Book a stay at this business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ... 9/10 Wonderful! (1,005 reviews) Convenient location. The pool is clean and fitness facility is quite good. Breakfast is excellent and in good service. Reviewed on Mar 23, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%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 CA $147 CA $160 total Mar 26 - Mar 27 includes taxes & fees Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ... 9.2/10 Wonderful! (2,279 reviews) Room was clean, lobby and staff friendly. This is our second time staying so we always enjoy coming. Reviewed on Mar 23, 2026 [](https://expedia.ca/Hotel-Search?startDate=26%2F03%2F2026&endDate=27%2F03%2F2026&selected=2678524&PinnedHotelID=2678524&HadPinnedHotel=true®ionId=6056879) ![Sleep Inn & Suites Winchester near University](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/554af346_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sleep Inn & Suites Winchester near University 140 Costello Dr Winchester VA CA $110 CA $119 total Apr 13 - Apr 14 includes taxes & fees Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ... 7.8/10 Good! (1,002 reviews) The room was very clean. The staff are friendly. Nice place to stay. Reviewed on Mar 23, 2026 [](https://expedia.ca/Hotel-Search?startDate=13%2F04%2F2026&endDate=14%2F04%2F2026&selected=892882&PinnedHotelID=892882&HadPinnedHotel=true®ionId=6056879) [See all 2,033 properties in Winchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=25%2F03%2F2026&endDate=26%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. ![Cozy Bear Cottage! Hot Tub! Warm toasty fireplace!](https://images.trvl-media.com/lodging/43000000/42620000/42617400/42617315/32780271_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Cozy Bear Cottage! Hot Tub! Warm toasty fireplace! Luray VA Stay at this cabin in Luray. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Luray Caverns and Dukes of Hazzard Museum are located ... [](https://expedia.ca/Luray-Hotels-A-Cozy-Bear-Cottage-Clean-And-Secluded.h42617315.Hotel-Information) ![Dreamtime - Modern A-frame Cabin w/ Hot tub](https://images.trvl-media.com/lodging/73000000/72940000/72936100/72936072/9fcb6e62_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Dreamtime - Modern A-frame Cabin w/ Hot tub Berkeley Springs WV Stay at this cabin in Berkeley Springs. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Frog Valley Artisans, LTD and Colonial Springs Spa ... 10/10 Exceptional! (57 reviews) The house was beautiful and well taken care of. We had everything we needed to just hold up cozy in the house. The hot tub was a great ammenity. Reviewed on Jan 23, 2026 [](https://expedia.ca/Berkeley-Springs-Hotels-Dreamtime-Modern-A-Frame-Cabin-W-Hot-Tub.h72936072.Hotel-Information) ![Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo](https://images.trvl-media.com/lodging/27000000/26970000/26968400/26968349/88605fc6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo Front Royal VA Stay at this cabin in Front Royal. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Glen Manor Vineyards and Shenandoah River State Park ... 9.6/10 Exceptional! (343 reviews) The space was cozy and nice. The view of the river was absolutely breathtaking from the back porch! Quiet and relaxing. Reviewed on Mar 23, 2026 [](https://expedia.ca/Winchester-Hotels-Log-Cabin-With-A-Spectacular-View-Of-The-Shenandoah-River-And-The-Massanutten-Mo.h26968349.Hotel-Information) [See all properties in Winchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=6056879&sort=VACATION_RENTAL) 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. ## Check Winchester hotel availability [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6056879&startDate=2026-03-24&endDate=2026-03-25)[Mar 24 - Mar 25](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6056879&startDate=2026-03-24&endDate=2026-03-25) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6056879&startDate=2026-03-25&endDate=2026-03-26)[Mar 25 - Mar 26](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6056879&startDate=2026-03-25&endDate=2026-03-26) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6056879&startDate=27%2F03%2F2026&endDate=29%2F03%2F2026)[Mar 27 - Mar 29](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6056879&startDate=27%2F03%2F2026&endDate=29%2F03%2F2026) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6056879&startDate=03%2F04%2F2026&endDate=05%2F04%2F2026)[Apr 3 - Apr 5](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6056879&startDate=03%2F04%2F2026&endDate=05%2F04%2F2026) ### Popular places to visit ![Gardens at Glen Burnie House.](https://images.trvl-media.com/place/6056879/a8b6bc61-16a0-4bd7-8e9c-ba5025791cbb.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Museum of the Shenandoah Valley 5/5(1 review) You can spend time exploring the galleries in Museum of the Shenandoah Valley during your trip to Winchester. Check out the top-notch restaurants or charming coffeehouses in this walkable area. [](https://expedia.ca/Museum-Of-The-Shenandoah-Valley-Winchester.d6127313.Vacation-Attraction) ![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) #### Shenandoah University 4/5(1 review) Enjoy the collegiate vibe when you visit Shenandoah University, during your trip to Winchester. While in this walkable area, you can savor the top-notch restaurants. [](https://expedia.ca/Shenandoah-University-Winchester.d6127311.Vacation-Attraction) #### ValleyHealth Winchester Medical Center Though ValleyHealth Winchester Medical Center might be what brings you to town, perhaps you'll have a chance to explore more of Winchester while you are here. [](https://expedia.ca/Winchester-Medical-Center-Winchester.d6164057.Vacation-Attraction) #### Apple Blossom Mall You can enjoy retail therapy at Apple Blossom Mall during your visit to Winchester. While in this walkable area, you can savor the top-notch restaurants. [](https://expedia.ca/Apple-Blossom-Mall-Winchester.d6164018.Vacation-Attraction) #### Shenandoah Valley Discovery Museum You can take time to visit Shenandoah Valley Discovery Museum during your travels to Winchester. While in this walkable area, you can savor the top-notch restaurants. [](https://expedia.ca/Shenandoah-Valley-Discovery-Museum-Old-Town-Winchester.d553248621587527659.Vacation-Attraction) ## Cities near Winchester ![If you're looking for a laugh, be sure to stop at Dinosaur Land on your next road trip. Filled to the brim with "life-size" dinosaur models, it's sure to be a hit with everyone! #roadtrip](https://images.trvl-media.com/place/553248621532661835/cdb5927f-8c77-4585-aebf-e34a8972f2f5.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### White Post ### Other places like Winchester - Cities near Winchester - Places of interest [White Post](https://expedia.ca/White-Post.dx184119) - [Jim Barnett Park ](https://expedia.ca/Jim-Barnett-Park-Winchester.d6164028.Vacation-Attraction) ![](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. 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