Title: Book the Best BOUTIQUE Hotels in Winchester in 2025 | 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) ![](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Boutique Hotels in Winchester, VA from CA $317 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Winchester Boutique Hotels Tonight [Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-10-17&endDate=2025-10-18&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 18 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-10-18&endDate=2025-10-19&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-10-17&endDate=2025-10-19&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-10-24&endDate=2025-10-26&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winchester Boutique Hotels ![Free daily full breakfast](https://images.trvl-media.com/lodging/16000000/15740000/15733600/15733502/0869608f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/15740000/15733600/15733502/w1568h1045x16y15-fb28d00b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Private Bathroom (Bridal Suite Room 260)](https://images.trvl-media.com/lodging/16000000/15740000/15733600/15733502/3a3f9489.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/16000000/15740000/15733600/15733502/8659900e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Evergreen Haymarket 9.4/10 Exceptional (131) "Clean,very nice facility " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew P CA $278 CA $317 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Haymarket-Hotels-Inn-At-Evergreen.h15733502.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/14000000/13090000/13080700/13080658/be536478.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/14000000/13090000/13080700/13080658/8c477719.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/14000000/13090000/13080700/13080658/630ad6af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed (The Lucile) | Living area](https://images.trvl-media.com/lodging/14000000/13090000/13080700/13080658/f6bdb27e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Laurance Luray 9.0/10 Wonderful (156) "We loved this sweet hotel, especially its cozy common area full of amenities (i.e., cookies). " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Wistar CA $357 CA $448 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Luray-Hotels-Hotel-Laurance.h13080658.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-01&endDate=2025-11-02®ionId=6056879&adults=2&specialized_stays_group_explore=boutique_property&sort=RECOMMENDED&openPlayBack=true) ## Top Winchester Hotel Reviews ![La Quinta Inn & Suites by Wyndham Winchester](//images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_y.jpg) ### La Quinta Inn & Suites by Wyndham Winchester 10/10 Excellent "Was just one night with group of friends. Location was great, easy check in and out, good breakfast and comfy beds. Would highly recommend. " [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![The George Washington Hotel, A Wyndham Grand Hotel](//images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c_y.jpg) ### The George Washington Hotel, A Wyndham Grand Hotel 10/10 Excellent "Very nice hotel " [](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ## Frequently asked questions ### What's there to see and do in Winchester? > Visitors speak positively about this destination's major shopping centers, scenic landscape, and interesting historical sites. Activities and attractions to experience around Winchester include Bright Box Theater, Winchester Little Theater, and Museum of the Shenandoah Valley. You might also like to explore more of the area and take in additional sights like Shenandoah Valley Discovery Museum, Abram's Delight, and Wayside Theater while you're here. ### What kind of weather should I plan for when I travel to Winchester? > Having a good idea of the weather in Winchester will help you enjoy your stay to the fullest. The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 36°F. Average annual precipitation for Winchester is 46 inches. ### What's the best way to get to my boutique hotel in Winchester? > You have a few options for traveling to and around Winchester. The closest major airport is Martinsburg, WV (MRB-Eastern West Virginia Regional), which is located 18 mi (28.9 km) from the heart of the city. 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