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 $155 - ![](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 [Nov 4 - Nov 5](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-11-04&endDate=2025-11-05&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 5 - Nov 6](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-11-05&endDate=2025-11-06&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-11-07&endDate=2025-11-09&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-11-14&endDate=2025-11-16&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=2025-11-18&endDate=2025-11-19®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) ![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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/a8e7d0d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/d6b37fa1.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 (1004) "Very nice hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul CA $177 CA $201 total includes taxes & fees Nov 20 - Nov 21 [](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) ![Private kitchen](https://images.trvl-media.com/lodging/76000000/75860000/75853400/75853307/6944d33b.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/d904aaa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pretty Little Apt by the Train II Old Town Winchester 9.6/10 Exceptional (5) "Great time. Love this city" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara B. CA $183 CA $304 total includes taxes & fees Nov 5 - Nov 6 [](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/76000000/75860000/75856800/75856721/547de25c.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) ![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) "We loved the character and personality kf both Winchester and" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jenna N. CA $205 CA $360 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Winchester-Hotels-Yellow-Submarine-Trendy-Basement-Apt-And-Courtyard.h75856721.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) ![Exterior detail](https://images.trvl-media.com/lodging/76000000/75860000/75856500/75856493/2c3dcc54.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) ![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) ### WonderClock House downtown vintage duplex w/ porches, steps to Handley Library Old Town Winchester 9.0/10 Wonderful (6) "This is a wonderful historic house in Old Town Winchester. The house is a duplex and is very room. It has the charm of a historic house, but modern amenities. It is very comfortable and check-in was extremely easy (we ended up arriving much later than we had planned, but had no problems accessing the house). The location is absolutely perfect, especially if you want to be in walking distance to all of the cute shops, cafes, and restaurants in the area. Our trip was very fast. We were in town... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wendy W. CA $288 CA $521 total includes taxes & fees Nov 12 - Nov 13 [](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) ![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) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/76000000/75860000/75853600/75853509/e0ae9bc5.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) "We stayed here overnight after our trip to Shenandoah. House had everything we needed for a peaceful night. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Subra S. CA $311 CA $549 total includes taxes & fees Nov 19 - Nov 20 [](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) ![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/ace40b05.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) ![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) "The apartment has an eclectic layout with great charm. Very clean and perfectly situated to Old Town. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Heather P. CA $260 CA $467 total includes taxes & fees Nov 5 - Nov 6 [](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/b8efa464.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) ![TV](https://images.trvl-media.com/lodging/120000000/119110000/119109900/119109888/bd1270e6.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 $548 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Winchester-Hotels-Magnolia-Wind-Elegant-3-BR-1BA-Loft-Apartment-Park-For-Free-And-Walk-Downtown.h119109888.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 (1056) "Excellent stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Haiyan CA $142 CA $155 total includes taxes & fees Nov 21 - Nov 22 [](https://www.expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/ffce1877.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/41cd029b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, desk, blackout drapes](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/d78ffc9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Winchester Winchester 9.2/10 Wonderful (2201) "One of the nicest places we’ve stayed " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $144 CA $157 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/737257e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/afbe118c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/w3837h2557x3y3-0ba96f9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/810f7f7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Front Royal Front Royal 9.0/10 Wonderful (1029) "Well located and very clean!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Odile CA $154 CA $172 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.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=2025-11-18&endDate=2025-11-19®ionId=6164092&adults=2&specialized_stays_group_explore=boutique_property&sort=RECOMMENDED&openPlayBack=true) ## Top Old Town Winchester Hotel Reviews ![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 "Service was great!!" [](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![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 "We had a pleasant stay, staff was really nice and the room was spotless. Easy check in, the breakfast in the morning was enjoyable. " [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.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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