Title: Windsor County Hotels with a Pool : Book the Right Hotels with a Pool Room in Windsor County, Vermont - 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) # Windsor County Hotels with a Pool ![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 ## Top Cities in Windsor County ![Ludlow showing street scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/94000/94298-Ludlow.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Ludlow [](https://expedia.ca/Ludlow-Hotels-Hotel-With-Pool.0-0-d8496-tHotelwithPool.Travel-Guide-Filter-Hotels) ![Woodstock featuring a house](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/94000/94311-Woodstock.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Woodstock [](https://expedia.ca/Woodstock-Hotels-Hotel-With-Pool.0-0-d10868-tHotelwithPool.Travel-Guide-Filter-Hotels) ![](https://mediaim.expedia.com/destination/2/212ecbf3b606238229538e223f3f57eb.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### White River Junction [](https://expedia.ca/White-River-Junction-Hotels-Hotel-With-Pool.0-0-d6294-tHotelwithPool.Travel-Guide-Filter-Hotels) ![Quechee featuring a river or creek, a bridge and tranquil scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/93000/93816-Central-Vermont.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Quechee [](https://expedia.ca/Quechee-Hotels-Hotel-With-Pool.0-0-d9580-tHotelwithPool.Travel-Guide-Filter-Hotels) ![](https://mediaim.expedia.com/destination/2/e6f5a135e5990faead3b19a2481c6d2b.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Windsor [](https://expedia.ca/Windsor-Hotels-Hotel-With-Pool.0-0-d7881-tHotelwithPool.Travel-Guide-Filter-Hotels) ![Central Vermont showing a house](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/94000/94646-Calvin-Coolidge-Historic-Site.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Plymouth [](https://expedia.ca/Plymouth-Hotels-Hotel-With-Pool.0-0-d146918-tHotelwithPool.Travel-Guide-Filter-Hotels) ![Weston](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/94000/94317-Weston.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Weston [](https://expedia.ca/Weston-Hotels-Hotel-With-Pool.0-0-d177460-tHotelwithPool.Travel-Guide-Filter-Hotels) ## Check availability on Windsor County Hotels with a Pool Tonight [Sep 22 - Sep 23](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2025-09-22&endDate=2025-09-23&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 23 - Sep 24](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2025-09-23&endDate=2025-09-24&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2025-09-26&endDate=2025-09-28&adults=2&amenities=POOL&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&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Windsor County Hotels with a Pool ![](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-Hotel-With-Pool.0-0-d553248635976432508-tHotelwithPool.Hotel-Filter-Destinations)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Windsor-County-Hotel-With-Pool.0-0-d553248635976432508-tHotelwithPool.Hotel-Filter-Destinations) ## Top Windsor County Hotel Reviews ![Align Inn Vermont](//images.trvl-media.com/lodging/1000000/10000/1200/1108/996cad8e_y.jpg) ### Align Inn Vermont 10/10 Excellent "Best hotel in the area, feels like home, the staff are so warm and welcoming, especially Chelsea. She gave us so many local recommendations, the Mexican restaurant next door is excellent. The rooms and cozy and clean. " [](https://expedia.ca/Quechee-Hotels-Quality-Inn-At-Quechee-Gorge.h1108.Hotel-Information) ![The Shire Woodstock](//images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg) ### The Shire Woodstock 10/10 Excellent "." [](https://expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information) ![The Quechee Inn at Marshland Farm](//images.trvl-media.com/lodging/2000000/1930000/1924800/1924710/c8372335_y.jpg) ### The Quechee Inn at Marshland Farm 10/10 Excellent "Beautiful property and large spacious room" [](https://expedia.ca/Quechee-Hotels-The-Quechee-Inn-At-Marshland-Farm.h1924710.Hotel-Information) ![Sleep Woodstock Motel](//images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/7b3a7c11_y.jpg) ### Sleep Woodstock Motel 10/10 Excellent "I come to area for medical visits often and Sleep Woodstock is my new favorite stay!" [](https://expedia.ca/Woodstock-Hotels-Sleep-Woodstock-Motel.h9658860.Hotel-Information) ![Jackson Gore Village](//images.trvl-media.com/lodging/3000000/2420000/2417100/2417009/7193c148_y.jpg) ### Jackson Gore Village 10/10 Excellent "The hotel was peaceful and clean, perfect for the weekend getaway." [](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 "Beautiful property and rooms are modern amenities in a quaint environment. " [](https://expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information) ![Hotel Coolidge](//images.trvl-media.com/lodging/2000000/1110000/1100200/1100199/w2880h2170x0y0-a69a5404_y.jpg) ### Hotel Coolidge 10/10 Excellent "Great location with great New England vibe. " [](https://expedia.ca/White-River-Junction-Hotels-Hotel-Coolidge.h1100199.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 "Friendly people " [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![Woodstock Inn & Resort](//images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff_y.jpg) ### Woodstock Inn & Resort 10/10 Excellent "What a wonderful inn. Same class as The Greenbrier and The Homestead. Old world charm." 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