Title: 10 Best Family & Kid Friendly Resorts in Windsor County for 2025 - Expedia.ca [Windsor County Hotels](https://expedia.ca/Destinations-In-Windsor-County.d553248635976432508.Hotel-Destinations)[Vacation Rentals in Windsor County](https://expedia.ca/Destinations-In-Windsor-County.d553248635976432508.Vacation-Rental-Destinations)[Windsor County Car Rentals](https://expedia.ca/Destinations-In-Windsor-County.d553248635976432508.Car-Rental-Destinations)[Windsor County Vacations](https://expedia.ca/Windsor-County.d553248635976432508.Destination-Travel-Guides) ![Weston showing interior views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/93000/93824-Central-Vermont.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Kid & Family Friendly Resorts in Windsor County ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Windsor County Family Hotels Tonight [Sep 27 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2025-09-27&endDate=2025-09-28&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 28 - Sep 29](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2025-09-28&endDate=2025-09-29&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2025-10-03&endDate=2025-10-05&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2025-10-10&endDate=2025-10-12&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Windsor County Family Hotels ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Windsor-County-Family-Hotel.0-0-d553248635976432508-tFamilyHotel.Hotel-Filter-Destinations)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Windsor-County-Family-Hotel.0-0-d553248635976432508-tFamilyHotel.Hotel-Filter-Destinations) ## Top Windsor County Hotel Reviews ![The Shire Woodstock](//images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg) ### The Shire Woodstock 10/10 Excellent "Great little motel. Clean, well appointed, friendly staff and walkable location. We did not have good weather, but great fire pits and chairs near river. " [](https://expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information) ![Woodstock Inn & Resort](//images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff_y.jpg) ### Woodstock Inn & Resort 10/10 Excellent "Clean room. Staff very polite and helpful " [](https://expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information) ![Align Inn Vermont](//images.trvl-media.com/lodging/1000000/10000/1200/1108/996cad8e_y.jpg) ### Align Inn Vermont 10/10 Excellent "The perfect hotel, Rachael the owner is beyond nice, she is always helpful and accommodating. Chelsea and Bill at the front desk could not be more helpful and kind. The rooms are impeccably clean and comfortable. " [](https://expedia.ca/Quechee-Hotels-Quality-Inn-At-Quechee-Gorge.h1108.Hotel-Information) ![Best Western Springfield Hotel](//images.trvl-media.com/lodging/1000000/20000/17800/17753/f0e2c480_y.jpg) ### Best Western Springfield Hotel 10/10 Excellent "Overall there were no issues with my stay. " [](https://expedia.ca/Springfield-Hotels-Best-Western-Springfield-Hotel.h17753.Hotel-Information) ![Jackson Gore Village](//images.trvl-media.com/lodging/3000000/2420000/2417100/2417009/7193c148_y.jpg) ### Jackson Gore Village 10/10 Excellent "The property was beautiful and well-maintained, and the staff were helpful and friendly. I had a great stay and will definitely be returning in the future. " [](https://expedia.ca/Ludlow-Hotels-Jackson-Gore-Village.h2417009.Hotel-Information) ![The Jackson ](//images.trvl-media.com/lodging/1000000/190000/181400/181337/f642c888_y.jpg) ### The Jackson 10/10 Excellent "Excellent Vintage style B&B. " [](https://expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information) ![Pointe at Castle Hill Resort](//images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/6a80e6c5_y.jpg) ### Pointe at Castle Hill Resort 10/10 Excellent "One day stay all went well" [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![Lincoln Inn & Gallery](//images.trvl-media.com/lodging/114000000/113900000/113896300/113896234/5d2c48fa_y.jpg) ### Lincoln Inn & Gallery 10/10 Excellent "Loved our stay here! Beautiful!" [](https://expedia.ca/Woodstock-Hotels-Lincoln-Inn-Gallery.h113896234.Hotel-Information) ![Sleep Woodstock Motel](//images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/7b3a7c11_y.jpg) ### Sleep Woodstock Motel 10/10 Excellent "Very hospitable and well appointed motel, 5 minute drive into woodstock. Very cute. spotlessly clean and had everything you couild need. Note - cannabis dispensary directly next door just FYI" [](https://expedia.ca/Woodstock-Hotels-Sleep-Woodstock-Motel.h9658860.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [Hotels near Billings Farm and Museum](https://www.expedia.ca/Billings-Farm-And-Museum-Hotels.0-l6175222-0.Travel-Guide-Filter-Hotels) - [Farmstay in Bridgewater](https://www.expedia.ca/Bridgewater-Agritourism.d553248635975851833-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Bridgewater](https://www.expedia.ca/Bridgewater-Apart-Hotels.d553248635975851833-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Bridgewater](https://www.expedia.ca/Bridgewater-Bed-And-Breakfast.d553248635975851833-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Condo Resorts in Bridgewater](https://www.expedia.ca/Bridgewater-Condominium-Resort.d553248635975851833-aaCondominiumResort.Travel-Guide-Accommodation) - [Guest Houses in Bridgewater](https://www.expedia.ca/Bridgewater-Guest-Houses.d553248635975851833-aaGuestHouses.Travel-Guide-Accommodation) - 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