Title: Book the Best Winchester FAMILY FRIENDLY Hotels from CA $93 - Kid-Friendly Hotels in Winchester, VA | 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 Family Hotels in Winchester, VA from CA $93 ![](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 Family Hotels Tonight [Oct 21 - Oct 22](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-10-21&endDate=2025-10-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Tomorrow [Oct 22 - Oct 23](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-10-22&endDate=2025-10-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) ## Top Winchester Family Hotels ![Lobby](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/e8922549.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) ![Lobby](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/5447905f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Microtel Inn & Suites by Wyndham Winchester Winchester 9.2/10 Wonderful (1344) "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/1000000/860000/855600/855557/10b5cc1e.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/5e0036d7.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 (1011) "Clean rooms friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ken 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/2000000/1660000/1652900/1652833/d0690cde.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/0f2ede5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/51a72e04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Winchester, VA Winchester 8.8/10 Excellent (1003) "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 2 - Nov 3 [](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) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/b96d495c.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) ![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) ### DoubleTree by Hilton Front Royal Blue Ridge Shadows Front Royal 9.0/10 Wonderful (1000) "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 Nov 2 - Nov 3 [](https://www.expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/e8983c22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/7e51069b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Winchester Winchester 9.2/10 Wonderful (1000) "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) ![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) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/ee4df7fa.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) ### Holiday Inn Winchester Se-Historic Gateway by IHG Winchester 9.0/10 Wonderful (1000) "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 10 - Nov 11 [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/be60c3ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Winchester N/Conference Center, VA Winchester 9.2/10 Wonderful (821) "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 Nov 2 - Nov 3 [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-NConference-Center.h424883.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2170000/2169500/2169428/689131eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily breakfast for a fee](https://images.trvl-media.com/lodging/3000000/2170000/2169500/2169428/a36008d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2170000/2169500/2169428/037b096c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2170000/2169500/2169428/a948cd9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Winchester Winchester 8.8/10 Excellent (499) "Great hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) DONNA D CA $134 CA $152 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Winchester-Hotels-Hilton-Garden-Inn-Winchester.h2169428.Hotel-Information) ![Coffee service](https://images.trvl-media.com/lodging/1000000/50000/43100/43087/f87cf676.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Laundry room](https://images.trvl-media.com/lodging/1000000/50000/43100/43087/3bfa30f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Laundry room](https://images.trvl-media.com/lodging/1000000/50000/43100/43087/7d3e25f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/50000/43100/43087/598f2666.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel 6 Winchester, VA Winchester 8.2/10 Very good (1012) "Well lit & clean with polite and attentive staff. Close to shops and eateries." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Zita CA $95 CA $108 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Winchester-Hotels-Motel-6-Winchester.h43087.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1100000/1090600/1090593/38caae92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1100000/1090600/1090593/326ab4b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1100000/1090600/1090593/424ee863.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room](https://images.trvl-media.com/lodging/2000000/1100000/1090600/1090593/91ceaee8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Winchester by IHG Winchester 9.0/10 Wonderful (789) "Great place to stay!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas CA $177 CA $192 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Express-Hotel-Suites-Winchester.h1090593.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=2025-11-05&endDate=2025-11-06®ionId=6056879&adults=2&travelerType=family_friendly&sort=RECOMMENDED&openPlayBack=true) ## Top Winchester Hotel Reviews ![Candlewood Suites Winchester by IHG](//images.trvl-media.com/lodging/2000000/1660000/1652900/1652870/0a2d8398_y.jpg) ### Candlewood Suites Winchester by IHG 10/10 Excellent "Megan is delightful" [](https://expedia.ca/Winchester-Hotels-Candlewood-Suites-Winchester.h1652870.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 "It was great the only thing bad .Breakfast only started at 7 am we had to leave at 6.30 am" [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Quality Inn Winchester](//images.trvl-media.com/lodging/1000000/180000/172900/172810/0fd2f943_y.jpg) ### Quality Inn Winchester 10/10 Excellent "Staff was super friendly and accommodating " [](https://expedia.ca/Winchester-Hotels-Quality-Inn.h172810.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 "Wonderful stay. " [](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![Spark by Hilton Winchester](//images.trvl-media.com/lodging/1000000/120000/117800/117743/ac575b89_y.jpg) ### Spark by Hilton Winchester 10/10 Excellent "Worked for me" [](https://expedia.ca/Winchester-Hotels-Spark-By-Hilton-Winchester.h117743.Hotel-Information) ![Travelodge by Wyndham Winchester](//images.trvl-media.com/lodging/1000000/10000/9600/9600/28616e5b_y.jpg) ### Travelodge by Wyndham Winchester 10/10 Excellent "Everything was fine just bed was a little soft for us." [](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![Courtyard by Marriott Winchester](//images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/8f242b36_y.jpg) ### Courtyard by Marriott Winchester 10/10 Excellent "The hotel is so clean and smells amazing. Staff was so helpful and pleasant. The room was clean and quite which was great for sleeping. Beds were comfortable. I will definitely stay there again. " [](https://expedia.ca/Winchester-Hotels-Courtyard-By-Marriott-Winchester.h1497898.Hotel-Information) ![Country Inn & Suites by Radisson, Winchester, VA](//images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/d0690cde_y.jpg) ### Country Inn & Suites by Radisson, Winchester, VA 10/10 Excellent "Always a great stay at this hotel. I highly recommend! " [](https://expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) ![Fairfield Inn & Suites by Marriott Winchester](//images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/w4000h2662x0y0-b556d792_y.jpg) ### Fairfield Inn & Suites by Marriott Winchester 10/10 Excellent "Everything was above par" [](https://expedia.ca/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.Hotel-Information) ## Frequently asked questions ### What's Winchester like for family-friendly vacations? > The historic destination of Winchester is a good choice if you've been thinking about a trip with your kids. The entertainment, soaring skyscrapers, and theaters are just a few things that make this an attractive family vacation spot. Arrange a flight into Martinsburg, WV (MRB-Eastern West Virginia Regional), which is located 18 mi (28.9 km) from the city center. ### What's the best hotel for a family vacation to Winchester? > [Microtel Inn & Suites by Wyndham Winchester](https://www.expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) is a hotel with an indoor pool and free parking, and it's a top choice on Expedia for families. Other good choices for your stay with the kids include [Country Inn & Suites by Radisson, Winchester, VA](https://www.expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) and [Quality Inn Winchester](https://www.expedia.ca/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information). ### How many family-friendly hotels should I expect to find in Winchester? > Expedia has 10 family-friendly hotels and other accommodations in Winchester. ### When's the best time to book a family-friendly vacation in Winchester? > 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 there to see and do with your family in Winchester? > While you are visiting Winchester, you and the family might want to check out some interesting spots such as Bright Box Theater, Winchester Little Theater, and Apple Blossom Mall. Make sure you have lots of time for activities like Handley Regional Library and Apple Valley Square Shopping Center. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - More ways to book - [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) - [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) - [Inns in Berryville](https://www.expedia.ca/Berryville-Inns.d184082-aaInns.Travel-Guide-Accommodation) - 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