Title: Book the Best BOUTIQUE Hotels in Old Town Winchester in 2025 | Expedia.ca [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)[Old Town Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Old-Town-Winchester.d6164092.Car-Rental-Guide)[Old Town Winchester Vacations](https://expedia.ca/Old-Town-Winchester.d6164092.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Boutique Hotels in Old Town Winchester, VA from CA $148 ![](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 Old Town Winchester Boutique Hotels Tonight [Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=6164092&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=6164092&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=6164092&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=6164092&startDate=2025-10-24&endDate=2025-10-26&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Old Town Winchester Boutique Hotels We don't have any properties that match your exact search [See all properties in Old Town Winchester](https://expedia.ca/Hotel-Search?startDate=2025-11-01&endDate=2025-11-02®ionId=6164092&adults=2) ## Recommended hotels in Old Town Winchester ![2 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/a8e7d0d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/bff9ad76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5707228d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The George Washington Hotel, A Wyndham Grand Hotel Old Town Winchester 9.4/10 Exceptional (1018) "Very nice hotel " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul CA $178 CA $201 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75853400/75853307/4d85dcf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/76000000/75860000/75853400/75853307/ccd1e83b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/76000000/75860000/75853400/75853307/0531b121.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/76000000/75860000/75853400/75853307/d904aaa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pretty Little Apt by the Train II Old Town Winchester 10/10 Exceptional (4) "Great time. Love this city" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara B. CA $182 CA $302 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Winchester-Hotels-Pretty-Little-Apt-By-The-Train-II.h75853307.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75860000/75856800/75856721/765a953b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75856800/75856721/85465173.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75856800/75856721/547de25c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/76000000/75860000/75856800/75856721/f2a89cc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Yellow Submarine trendy basement apt and courtyard Old Town Winchester 9.0/10 Wonderful (2) "Very clean and comfortable. Really cool furniture pieces. Nice kitchen, dining room, living room. Will stay here again when in the area. " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric N. CA $205 CA $364 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Winchester-Hotels-Yellow-Submarine-Trendy-Basement-Apt-Wcourtyard.h75856721.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/108000000/107900000/107895800/107895789/w1117h810x5y0-b88c2c12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107900000/107895800/107895789/0da8d534.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107900000/107895800/107895789/288bbbf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/108000000/107900000/107895800/107895789/w1025h1046x4y3-ad71c285.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Morocco Loft 2BR overlooking city walking mall Old Town Winchester 10/10 Exceptional (2) "Great property with all the comforts of home" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristen R. CA $250 CA $450 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Winchester-Hotels-Morocco-Loft-2BR-Overlooking-City-Walking-Mall.h107895789.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/76000000/75860000/75856500/75856493/80b59f6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/76000000/75860000/75856500/75856493/w1413h1055x0y0-6561893b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75856500/75856493/31a46244.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/76000000/75860000/75856500/75856493/2c3dcc54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### WonderClock House downtown vintage duplex w/ porches, steps to Handley Library Old Town Winchester 9.0/10 Wonderful (6) "Our Wonder Clock stay was great. Everything was as expected. Location to downtown was awesome and very easily walkable. Our stay was cut short unexpectedly, but we would stay here again! The host was very responsive to one concern we had and was willing to fix immediately. " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Angela S. CA $287 CA $519 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Winchester-Hotels-WonderClock-House-Downtown-Vintage-Duplex-W-Porches.h75856493.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/76000000/75860000/75853600/75853509/49b61b8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/76000000/75860000/75853600/75853509/b3502d94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/76000000/75860000/75853600/75853509/aac25142.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75860000/75853600/75853509/facc3b4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Scarborough Fair walk to downtown two story apt Old Town Winchester 9.6/10 Exceptional (4) "Charming home! Lovely decor. Was perfect for our stay. Great location, walkable to the historical district. Host was very friendly and communicative. " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephanie L. CA $311 CA $554 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Winchester-Hotels-Scarborough-Fair-Walk-To-Downtown-Two-Story-Apt.h75853509.Hotel-Information) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/434367ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/b00d8fd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/4cf065b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/2359633a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Nostalgia Lane in the heart of the city Old Town Winchester 8.8/10 Excellent (13) "Great location in the heart of Winchester. Walking distance to everything. " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew N. CA $259 CA $454 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Winchester-Hotels-Nostalgia-Lane-In-The-Heart-Of-The-City.h75852258.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/120000000/119110000/119109900/119109888/bb213bf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/120000000/119110000/119109900/119109888/685d4771.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/120000000/119110000/119109900/119109888/bd1270e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119110000/119109900/119109888/23f512b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown Old Town Winchester CA $309 CA $543 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Winchester-Hotels-Magnolia-Wind-Elegant-3-BR-1BA-Loft-Apartment-Park-For-Free-And-Walk-Downtown.h119109888.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/76000000/75860000/75853900/75853887/11bbc02b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75853900/75853887/5351846f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75853900/75853887/81902a90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75853900/75853887/9e695565.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Blue Door steps from Handley Library Old Town Winchester 5.4/10 (3) "Perfect. Met all expectations. Small but Great." ![](https://a.travel-assets.com/egds/marks/flags/us.svg) derric3k CA $161 CA $270 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Winchester-Hotels-The-Blue-Door-Steps-From-Handley-Library.h75853887.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/6a36301f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/6a37f73c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/f8e3941a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Winchester Winchester 9.4/10 Exceptional (1029) "The breakfast was good and a quiet place to stay " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Lawrence CA $136 CA $148 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.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=6164092&adults=2&specialized_stays_group_explore=boutique_property&sort=RECOMMENDED&openPlayBack=true) ## Top Old Town 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 Old Town Winchester? > The bars, shopping, and restaurants are just some of the things to enjoy while you're in the area. Attractions and activities to experience around Old Town Winchester include Bright Box Theater, Shenandoah Valley Discovery Museum, and Handley Regional Library. While you're here, you might also like to explore more of the area and take in additional sights like Winchester Little Theater, Patsy Cline Historic House, and Museum of the Shenandoah Valley. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [4 Star Hotels in Stephens City](https://www.expedia.ca/4Star-Stephens-City-Hotels.s40-0-d12076.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Winchester](https://www.expedia.ca/4Star-Winchester-Hotels.s40-0-d6056879.Travel-Guide-Filter-Hotels) - [Hotels near Apple Blossom Mall](https://www.expedia.ca/Apple-Blossom-Mall-Hotels.0-l6164018-0.Travel-Guide-Filter-Hotels) - [Historic Hotels in Berryville](https://www.expedia.ca/Berryville-Hotels-Historic-Hotel.0-0-d184082-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Berryville](https://www.expedia.ca/Berryville-Hotels-Luxury-Hotel.0-0-d184082-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Berryville Hotels](https://www.expedia.ca/Berryville-Hotels.d184082.Travel-Guide-Hotels) - 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