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) ![Woodstock showing heritage architecture](https://images.trvl-media.com/place/10868/954ac78e-5f6e-477c-83db-652840be94bb.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Windsor County Hotels with a Pool - ![](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 ## 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) ![](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) ![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) ![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 [Nov 11 - Nov 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2025-11-11&endDate=2025-11-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 12 - Nov 13](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2025-11-12&endDate=2025-11-13&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2025-11-14&endDate=2025-11-16&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635976432508&startDate=2025-11-21&endDate=2025-11-23&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 ![The Vesper ](//images.trvl-media.com/lodging/104000000/103420000/103415500/103415437/ae1d5a64_y.jpg) ### The Vesper 10/10 Excellent "A Perfect Stay in the Heart of Woodstock Vesper Bed and Breakfast is a gem in downtown Woodstock. The location couldn’t be better—just a short walk to all the shops, restaurants, and local sights, yet tucked away enough to feel peaceful and private. The rooms are spotless, minimalist, and thoughtfully designed for comfort without unnecessary fuss—simple, cozy, and just right after a day exploring town. Host Jessica is absolutely wonderful—warm, welcoming, and genuinely invested in making your stay easy and enjoyable. Everything about the place feels calm, easy, and well cared for. If you’re looking for a relaxed, comfortable stay in the perfect spot, this is it. We’ll definitely be back—and you should stay here too." [](https://expedia.ca/Woodstock-Hotels-The-Vesper.h103415437.Hotel-Information) ![The Shire Woodstock](//images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg) ### The Shire Woodstock 10/10 Excellent "Large, clean room with nice view. Unique. " [](https://expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.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 "Clean room Staff went over and above" [](https://expedia.ca/Springfield-Hotels-Best-Western-Springfield-Hotel.h17753.Hotel-Information) ![Align Inn Vermont](//images.trvl-media.com/lodging/1000000/10000/1200/1108/996cad8e_y.jpg) ### Align Inn Vermont 10/10 Excellent "The room was clean and comfortable, the front desk staff was friendly (especially considering we arrived really late at night), and the breakfast was solid. " [](https://expedia.ca/Quechee-Hotels-Quality-Inn-At-Quechee-Gorge.h1108.Hotel-Information) ![Hotel Coolidge](//images.trvl-media.com/lodging/2000000/1110000/1100200/1100199/w2880h2170x0y0-a69a5404_y.jpg) ### Hotel Coolidge 10/10 Excellent "As always, a real pleasure.. and we've stayed there many times in the last 20 years! Clean rooms, cheerful & helpful staff. Yay!" [](https://expedia.ca/White-River-Junction-Hotels-Hotel-Coolidge.h1100199.Hotel-Information) ![On The River Inn](//images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/528a7f5b_y.jpg) ### On The River Inn 10/10 Excellent "Staff were fantastic " [](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.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 "Nice clean room and friendly staff. I was there off season (early November) so some restaurants weren’t open but there were still plenty of options. " [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![Holiday Inn Club Vacations Mount Ascutney Resort by IHG](//images.trvl-media.com/lodging/1000000/430000/425200/425171/fead325a_y.jpg) ### Holiday Inn Club Vacations Mount Ascutney Resort by IHG 10/10 Excellent "Everything was well stocked. Great job, Holiday Inn Club vacations!" [](https://expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information) ![The Jackson ](//images.trvl-media.com/lodging/1000000/190000/181400/181337/f642c888_y.jpg) ### The Jackson 10/10 Excellent "Loved the casual, comfortable, easy atmosphere. Homey and welcoming but never overbearing. Staff were all wonderful and personable. 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