Title: Book the Best Winchester Historic District FAMILY FRIENDLY Hotels - Kid-Friendly Hotels in Winchester Historic District, Winchester | Expedia.ca [Winchester Historic District Travel Guide](https://expedia.ca/Winchester-Winchester-Historic-District.dx918789051029594112)[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 Historic District Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester-Historic-District.d918789051029594112.Car-Rental-Guide)[Winchester Historic District Vacations](https://expedia.ca/Winchester-Historic-District.d918789051029594112.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Family Hotels in Winchester Historic District, Winchester ![](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 Historic District Family Hotels Tonight [Oct 19 - Oct 20](https://www.expedia.ca/Hotel-Search?regionId=918789051029594112&startDate=2025-10-19&endDate=2025-10-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Tomorrow [Oct 20 - Oct 21](https://www.expedia.ca/Hotel-Search?regionId=918789051029594112&startDate=2025-10-20&endDate=2025-10-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=918789051029594112&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=918789051029594112&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) ## Top Winchester Historic District Family Hotels ![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) ![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) ![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) ### 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. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric N. CA $205 CA $361 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Winchester-Hotels-Yellow-Submarine-Trendy-Basement-Apt-Wcourtyard.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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75856500/75856493/cf8e60e5.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. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angela S. CA $287 CA $519 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Winchester-Hotels-WonderClock-House-Downtown-Vintage-Duplex-W-Porches.h75856493.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) ![Dining](https://images.trvl-media.com/lodging/76000000/75860000/75853900/75853887/1984db96.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." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) derric3k CA $161 CA $270 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Winchester-Hotels-The-Blue-Door-Steps-From-Handley-Library.h75853887.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/5447905f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/8897f4a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/3e194222.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Microtel Inn & Suites by Wyndham Winchester Winchester 9.2/10 Wonderful (1341) "Great place with very cute rooms!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) kristy CA $113 CA $123 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/d0690cde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/e0021d58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/0f2ede5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/b06f3533.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Winchester, VA Winchester 8.8/10 Excellent (1021) "Our third stay here. Very nice and convenient to 81. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dawn CA $128 CA $139 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/204cbf3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/ad5604d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/9cf3d079.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/b96d495c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Front Royal Blue Ridge Shadows Front Royal 9.0/10 Wonderful (1006) "Nice place. Good bar." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gerald CA $160 CA $180 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/c68804b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/b6f40366.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/7ff8d7be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed (Additional Living Area)](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/aeec97ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Winchester Se-Historic Gateway by IHG Winchester 9.0/10 Wonderful (1008) "Great stay value" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy CA $123 CA $138 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/10b5cc1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/a71565c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/325feec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/4c979d71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Front Royal Front Royal 7.6/10 Good (1008) "We have stayed here many of times love it!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tina CA $83 CA $93 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Winchester-Hotels-Super-8-By-Wyndham-Front-Royal.h855557.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/c7da6581.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/9e37f17d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/cd85ec17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/e8983c22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Winchester Winchester 9.2/10 Wonderful (1018) "Staff was super friendly and accommodating " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $109 CA $119 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information) ![Snack bar](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/cba33bb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/be60c3ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/b2c8e1ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One king study sofabed non smoking](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/311c50f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Winchester N/Conference Center, VA Winchester 9.2/10 Wonderful (819) "Great place to stay. Super clean and comfortable beds." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roy Allen CA $148 CA $168 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-NConference-Center.h424883.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=2025-11-02&endDate=2025-11-03®ionId=918789051029594112&adults=2&travelerType=family_friendly&sort=RECOMMENDED&openPlayBack=true) ## Top Winchester Historic District Hotel Reviews ## Frequently asked questions ### What's Winchester Historic District like for family-friendly vacations? > If you've been thinking about a vacation with your kids, Winchester Historic District is a good choice. There are some entertaining activities you and the family might enjoy. Arrange a flight into Martinsburg, WV (MRB-Eastern West Virginia Regional), which is located 18 mi (28.9 km) from the center of Winchester Historic District. ### What's there to see and do with your family in Winchester Historic District? > Bright Box Theater, Winchester Little Theater, and Handley Regional Library are interesting attractions you and your family will enjoy exploring while you are staying in Winchester Historic District. Make sure you have lots of time for activities like Apple Blossom Mall and Dinosaur Land. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - [3 Star Hotels in Old Town Winchester](https://www.expedia.ca/3Star-Old-Town-Winchester-Winchester-Hotels.s30-n6164092-0.Travel-Guide-Filter-Hotels) - [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) - [Berryville Hotels](https://www.expedia.ca/Berryville-Hotels.d184082.Travel-Guide-Hotels) - [Inns in Berryville](https://www.expedia.ca/Berryville-Inns.d184082-aaInns.Travel-Guide-Accommodation) - [Apartments in Boyce](https://www.expedia.ca/Boyce-Apartments.d184084-aaApartments.Travel-Guide-Accommodation) - 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[Flights from Toronto (YYZ) to Winchester (WGO)](https://www.expedia.ca/lp/flights/yyz/wgo/toronto-to-winchester) - [Appleland Sports Center](https://www.expedia.ca/Appleland-Sports-Center-Stephens-City.d553248621587477489.Vacation-Attraction) - [Jim Barnett Park](https://www.expedia.ca/Jim-Barnett-Park-Winchester.d6164028.Vacation-Attraction) - [Winchester Vacations](https://www.expedia.ca/Winchester.d6056879.Destination-Travel-Guides) - [Budget Rental Cars in Winchester](https://www.expedia.ca/Budget-Car-Rentals-In-Winchester.d6056879-c39.Car-Rental-Guide-Suppliers) - [Car rental Winchester](https://www.expedia.ca/Car-Rentals-In-Winchester.d6056879.Car-Rental-Guide) - [National Car Rental Rental Cars in Winchester](https://www.expedia.ca/National-Car-Rental-Car-Rentals-In-Winchester.d6056879-c42.Car-Rental-Guide-Suppliers) - [Winchester Vacation Rentals](https://www.expedia.ca/Winchester-Vacation-Rentals.d6056879.Travel-Guide-VacationRentals) - [Things to do in Winchester](https://www.expedia.ca/Things-To-Do-In-Winchester.d6056879.Travel-Guide-Activities)