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) ![Winchester](https://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.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 ![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 CA $134 CA $146 total Feb 8 - Feb 9 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! (2,259 reviews) Clean, bright, and up-to-date hotel. Friendly staff, warm pool, nice little exercise room. Standard hotel breakfast fare, but it was good, and staff was very kind about the bit of mess our toddlers made while eating (we offered to tidy up, and they said it was no problem!). Great experience. Reviewed on Jan 31, 2026 [](https://expedia.ca/Hotel-Search?startDate=08%2F02%2F2026&endDate=09%2F02%2F2026&selected=2678524&PinnedHotelID=2678524&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 CA $96 CA $104 total Feb 8 - Feb 9 includes taxes & fees Stay at this motel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ... 8.4/10 Very Good! (1,076 reviews) Clean place, breakfast ok, warm and comfy, would stay again Reviewed on Jan 30, 2026 [](https://expedia.ca/Hotel-Search?startDate=08%2F02%2F2026&endDate=09%2F02%2F2026&selected=9600&PinnedHotelID=9600&HadPinnedHotel=true®ionId=6056879) ![The George Washington Hotel, A Wyndham Grand Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The George Washington Hotel, A Wyndham Grand Hotel 103 E Piccadilly St Winchester VA CA $173 CA $196 total Feb 17 - Feb 18 includes taxes & fees Book a stay at this spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ... 9.2/10 Wonderful! (1,000 reviews) Clean nice room Great location for restaurants Reviewed on Jan 28, 2026 [](https://expedia.ca/Hotel-Search?startDate=17%2F02%2F2026&endDate=18%2F02%2F2026&selected=1364026&PinnedHotelID=1364026&HadPinnedHotel=true®ionId=6056879) [See all 2,072 properties in Winchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=08%2F02%2F2026&endDate=09%2F02%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. ![Star view cabin-Riverfront ](https://images.trvl-media.com/lodging/31000000/30790000/30788500/30788475/2cb5e40f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Star view cabin-Riverfront Rileyville VA Stay at this cabin in Rileyville. Enjoy laundry facilities, tennis courts, and patios. Our guests praise the property condition in our reviews. Popular attractions ... 9.6/10 Exceptional! (310 reviews) We came during an unexpected snow storm and still had the best time. She came over to introduce herself to us and was absolutely amazing, welcoming, and accommodating to our needs during the storm and offered us an extra night if we got stuck. The cabin was the perfect size with the best Mountain ... Reviewed on Jan 25, 2026 [](https://expedia.ca/Rileyville-Hotels-Star-View-Cabin-Riverfront.h30788475.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 ... 9.8/10 Exceptional! (53 reviews) Lovely little cabin on a wooded lot. Loved the wood stove and the hot tub. Such a relaxing experience. Reviewed on Jan 18, 2026 [](https://expedia.ca/Berkeley-Springs-Hotels-Dreamtime-Modern-A-Frame-Cabin-W-Hot-Tub.h72936072.Hotel-Information) ![Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek. ](https://images.trvl-media.com/lodging/28000000/27140000/27132300/27132250/w4320h3258x0y0-de7068d1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek. Berkeley Springs WV Stay at this cabin in Berkeley Springs. Enjoy laundry facilities, patios, and cable/satellite TV service. Popular attractions Cacapon Golf Course and Colonial ... 9.8/10 Exceptional! (284 reviews) Jackie was exceptionally communicative and collaborative regarding our trip that would be disrupted by the recent snow storm. I really appreciate how detailed Jackie was, how she checked in with me regularly and worked with me so that I could still enjoy the beautiful rental for a night before the ... Reviewed on Jan 27, 2026 [](https://expedia.ca/Berkeley-Springs-Hotels-Romantic-Woodland-Retreat-With-Hot-Tub-Private-Forest-Views-NEWLY-RENOVATED.h27132250.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=2026-02-07&endDate=2026-02-08)[Feb 7 - Feb 8](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6056879&startDate=2026-02-07&endDate=2026-02-08) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6056879&startDate=2026-02-08&endDate=2026-02-09)[Feb 8 - Feb 9](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6056879&startDate=2026-02-08&endDate=2026-02-09) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6056879&startDate=13%2F02%2F2026&endDate=15%2F02%2F2026)[Feb 13 - Feb 15](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6056879&startDate=13%2F02%2F2026&endDate=15%2F02%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 charming coffeehouses or top-notch restaurants 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 top-notch restaurants or charming coffeehouses in this walkable area. [](https://expedia.ca/Jim-Barnett-Park-Winchester.d6164028.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) #### 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) #### Patsy Cline Historic House You can find out about the history of Winchester with a stop at Patsy Cline Historic House. While in this walkable area, you can savor the top-notch restaurants. [](https://expedia.ca/Patsy-Cline-Historic-House-Winchester.d553248621532661841.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) ## 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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