Title: Book the Best Winchester FAMILY FRIENDLY Hotels from CA $71 - Kid-Friendly Hotels in Winchester, IN | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d6046207.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d6046207.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d6046207.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d6046207.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/family_friendly.jpeg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Family Hotels in Winchester, IN from CA $71 - ![](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 [Dec 25 - Dec 26](https://www.expedia.ca/Hotel-Search?regionId=6046207&startDate=2025-12-25&endDate=2025-12-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Tomorrow [Dec 26 - Dec 27](https://www.expedia.ca/Hotel-Search?regionId=6046207&startDate=2025-12-26&endDate=2025-12-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) This weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6046207&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6046207&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) ## Our top choices for Winchester family-friendly hotels ![Room, 1 King Bed, Accessible, Non Smoking (Mobility, Bathtub w/Grab Bars)](https://images.trvl-media.com/lodging/1000000/10000/4400/4345/97f2f944.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4400/4345/449ea658.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/10000/4400/4345/d1a94e5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/4400/4345/4f171030.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baymont by Wyndham Richmond I-70 [](https://www.expedia.ca/Richmond-Hotels-Comfort-Inn-Richmond-I-70.h4345.Hotel-Information) Richmond 8.4/10 Very good (1000) "Breakfast was fresh and good " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian CA $92 CA $103 total includes taxes & fees Dec 26 - Dec 27 [](https://www.expedia.ca/Richmond-Hotels-Comfort-Inn-Richmond-I-70.h4345.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/1000000/60000/50200/50102/bd1ec505.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/60000/50200/50102/a66e4fa5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/60000/50200/50102/fd5cd6eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/60000/50200/50102/e8a5ed00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel 6 Richmond, IN [](https://www.expedia.ca/Richmond-Hotels-Motel-6-Richmond.h50102.Hotel-Information) Richmond 7.8/10 Good (1000) "Yes the room was clean the staff was helpful and courteous and informative about the festivities that were going on in town" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $64 CA $71 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Richmond-Hotels-Motel-6-Richmond.h50102.Hotel-Information) ![Standard King Non Smoking](https://images.trvl-media.com/lodging/1000000/30000/25900/25869/ebc0f494.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/30000/25900/25869/212982c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/30000/25900/25869/bca78e68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee service](https://images.trvl-media.com/lodging/1000000/30000/25900/25869/b57a6af7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn and Conference Center [](https://www.expedia.ca/Richmond-Hotels-Quality-Inn-And-Conference-Center.h25869.Hotel-Information) Richmond 6.6/10 (1000) "The overnight clerk was very friendly and helpful. The room was clean and spacious." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica CA $64 CA $72 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/Richmond-Hotels-Quality-Inn-And-Conference-Center.h25869.Hotel-Information) ![Food court](https://images.trvl-media.com/lodging/1000000/260000/251600/251530/d93a0730.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/260000/251600/251530/451c7d70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/260000/251600/251530/0c112d6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking, Refrigerator & Microwave](https://images.trvl-media.com/lodging/1000000/260000/251600/251530/6c85147d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Richmond Indiana I-70 [](https://www.expedia.ca/Richmond-Hotels-Best-Western-Classic-Inn.h251530.Hotel-Information) Richmond 8.4/10 Very good (1000) "New facility, best hotel I’ve stayed in recently!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Antonia CA $128 CA $143 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Richmond-Hotels-Best-Western-Classic-Inn.h251530.Hotel-Information) ![Bathroom sink](https://images.trvl-media.com/lodging/1000000/800000/796900/796880/752ec8a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/800000/796900/796880/fb817b68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/800000/796900/796880/2a2456bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/800000/796900/796880/9c1e874b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Travelodge by Wyndham Richmond IN [](https://www.expedia.ca/Richmond-Hotels-Travelodge-By-Wyndham-Richmond-IN.h796880.Hotel-Information) Richmond 7.0/10 Good (440) "This motel/hotel was conveniently located off the highway and reasonably priced for what they provided." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $70 CA $79 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Richmond-Hotels-Travelodge-By-Wyndham-Richmond-IN.h796880.Hotel-Information) ![Room, 1 King Bed, Non Smoking, Jetted Tub](https://images.trvl-media.com/lodging/1000000/70000/60600/60521/74d1da02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/70000/60600/60521/2d4f8dfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/70000/60600/60521/e4e82fa8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/70000/60600/60521/e2971d78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Greenville North [](https://www.expedia.ca/Sidney-Hotels-Quality-Inn-Greenville-North.h60521.Hotel-Information) Greenville 8.2/10 Very good (348) "Great value. I stay here once twice a year." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William CA $139 CA $164 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Sidney-Hotels-Quality-Inn-Greenville-North.h60521.Hotel-Information) ![Double Room, 2 Double Beds, Non Smoking, Kitchenette](https://images.trvl-media.com/lodging/3000000/2150000/2141800/2141769/6054e777.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Non Smoking](https://images.trvl-media.com/lodging/3000000/2150000/2141800/2141769/c0429424.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2150000/2141800/2141769/f09c6c47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, 2 Double Beds, Non Smoking, Kitchenette | Private kitchen](https://images.trvl-media.com/lodging/3000000/2150000/2141800/2141769/45b3e79e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Muncie Near University [](https://www.expedia.ca/Muncie-Hotels-Comfort-Inn-Suites-Muncie.h2141769.Hotel-Information) Muncie 8.4/10 Very good (724) "We had a good stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rodney CA $118 CA $132 total includes taxes & fees Dec 27 - Dec 28 [](https://www.expedia.ca/Muncie-Hotels-Comfort-Inn-Suites-Muncie.h2141769.Hotel-Information) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/6000000/5250000/5248500/5248460/3f656adc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking, Refrigerator & Microwave (with Sofabed)](https://images.trvl-media.com/lodging/6000000/5250000/5248500/5248460/127e8ced.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/6000000/5250000/5248500/5248460/53012ed4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5250000/5248500/5248460/a60c171c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Surestay By Best Western Greenville [](https://www.expedia.ca/Greenville-Hotels-Surestay-By-Best-Western-Greenville.h5248460.Hotel-Information) Greenville 7.8/10 Good (381) "Parking was good, room was clean but spatub didn’t work, area was clean and nice. Staff was great. But breakfast was subpar, no selection and can't even say its a continental breakfast. No protein only fruit and yogurt." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christina CA $111 CA $126 total includes taxes & fees Dec 27 - Dec 28 [](https://www.expedia.ca/Greenville-Hotels-Surestay-By-Best-Western-Greenville.h5248460.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/6000000/5260000/5259300/5259255/3db22d65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/6000000/5260000/5259300/5259255/90990d74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/6000000/5260000/5259300/5259255/cb1c6484.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily to-go breakfast (USD 10.00 per person)](https://images.trvl-media.com/lodging/6000000/5260000/5259300/5259255/7efa55fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Richmond by IHG [](https://www.expedia.ca/Richmond-Hotels-Holiday-Inn-Richmond.h5259255.Hotel-Information) Richmond 8.4/10 Very good (775) "It was great." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris CA $122 CA $136 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Richmond-Hotels-Holiday-Inn-Richmond.h5259255.Hotel-Information) ![Room, 2 Queen Beds](https://images.trvl-media.com/lodging/13000000/12760000/12755900/12755848/6aef882b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily to-go breakfast for a fee](https://images.trvl-media.com/lodging/13000000/12760000/12755900/12755848/79a5f4d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12760000/12755900/12755848/a38251f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/13000000/12760000/12755900/12755848/87c9935d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard Muncie at Horizon Convention Center [](https://www.expedia.ca/Muncie-Hotels-Courtyard-Muncie-At-Horizon-Convention-Center.h12755848.Hotel-Information) Muncie 9.0/10 Wonderful (863) "Everything was good" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julee CA $162 CA $181 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Muncie-Hotels-Courtyard-Muncie-At-Horizon-Convention-Center.h12755848.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=2026-01-08&endDate=2026-01-09®ionId=6046207&adults=2&travelerType=family_friendly&sort=RECOMMENDED&openPlayBack=true) ## Top Winchester Hotel Reviews ![Hampton Inn & Suites Richmond, IN](https://images.trvl-media.com/lodging/2000000/1600000/1590100/1590037/1e53a5db_y.jpg) ### Hampton Inn & Suites Richmond, IN 10/10 Excellent "Breakfast is consistently fresh. Rooms are clean and quiet. Pet friendly!" [](https://expedia.ca/Richmond-Hotels-Hampton-Inn-Suites-Richmond.h1590037.Hotel-Information) ![Baymont by Wyndham Richmond I-70](https://images.trvl-media.com/lodging/1000000/10000/4400/4345/97f2f944_y.jpg) ### Baymont by Wyndham Richmond I-70 10/10 Excellent "Debbie was at the front desk and she was awesome ! Friendly, fast and courteous ! " [](https://expedia.ca/Richmond-Hotels-Comfort-Inn-Richmond-I-70.h4345.Hotel-Information) ![Baymont by Wyndham Muncie Near Ball State University](https://images.trvl-media.com/lodging/1000000/10000/3300/3204/39faaa1f_y.jpg) ### Baymont by Wyndham Muncie Near Ball State University 10/10 Excellent "yes" [](https://expedia.ca/Muncie-Hotels-Baymont-By-Wyndham-Muncie-Near-Ball-State-University.h3204.Hotel-Information) ![Motel 6 Richmond, IN](https://images.trvl-media.com/lodging/1000000/60000/50200/50102/3e0f69fd_y.jpg) ### Motel 6 Richmond, IN 10/10 Excellent "VERY NICE" [](https://expedia.ca/Richmond-Hotels-Motel-6-Richmond.h50102.Hotel-Information) ![Hampton Inn & Suites Muncie](https://images.trvl-media.com/lodging/3000000/2050000/2041500/2041430/9c9f9d6d_y.jpg) ### Hampton Inn & Suites Muncie 10/10 Excellent "Fast check in good location " [](https://expedia.ca/Muncie-Hotels-Hampton-Inn-Suites-Muncie.h2041430.Hotel-Information) ![Best Western Plus Richmond Indiana I-70](https://images.trvl-media.com/lodging/1000000/260000/251600/251530/d93a0730_y.jpg) ### Best Western Plus Richmond Indiana I-70 10/10 Excellent "Yes" [](https://expedia.ca/Richmond-Hotels-Best-Western-Classic-Inn.h251530.Hotel-Information) ![Holiday Inn Express Hotel & Suites Greenville by IHG](https://images.trvl-media.com/lodging/1000000/870000/861300/861235/292b4768_y.jpg) ### Holiday Inn Express Hotel & Suites Greenville by IHG 10/10 Excellent "Caring staff. Wonderful swim in the pool. Facility is very clean and bright with beautiful holiday decorations. Thanks so much. Will stay again on my next trip. " [](https://expedia.ca/Sidney-Hotels-Holiday-Inn-Express-Hotel-Suites-Greenville.h861235.Hotel-Information) ![Holiday Inn Express Richmond by IHG](https://images.trvl-media.com/lodging/6000000/5260000/5259300/5259255/3db22d65_y.jpg) ### Holiday Inn Express Richmond by IHG 10/10 Excellent "They greeted me like a long lost friend. When we went to our room we were blown away at how spacious it was. Made us to feel really special." [](https://expedia.ca/Richmond-Hotels-Holiday-Inn-Richmond.h5259255.Hotel-Information) ![Comfort Inn & Suites Muncie Near University](https://images.trvl-media.com/lodging/3000000/2150000/2141800/2141769/6054e777_y.jpg) ### Comfort Inn & Suites Muncie Near University 10/10 Excellent "The room was clean and the staff very courteous. " [](https://expedia.ca/Muncie-Hotels-Comfort-Inn-Suites-Muncie.h2141769.Hotel-Information) ## Frequently asked questions ### What's Winchester like for family-friendly vacations? ### When's the best time to book a family-friendly vacation in Winchester? ### What's there to see and do with your family in Winchester? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [5 Star Hotels in East Central Indiana ](https://www.expedia.ca/5Star-East-Central-Indiana-Hotels.s50-0-d6233870.Travel-Guide-Filter-Hotels) - [Apartments in Albany ](https://www.expedia.ca/Albany-Apartments.d553248634983410143-aaApartments.Travel-Guide-Accommodation) - [Cheap Hotels in Albany ](https://www.expedia.ca/Albany-Hotels-Cheap-Hotels.0-0-d553248634983410143-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Albany ](https://www.expedia.ca/Albany-Hotels-Hotel-With-Pool.0-0-d553248634983410143-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Albany Hotels ](https://www.expedia.ca/Albany-Hotels.d553248634983410143.Travel-Guide-Hotels) - 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