Title: Orange County Hotels with a Pool : Book the Right Hotels with a Pool Room in Orange County, New York - Expedia.ca [Orange County Hotels](https://expedia.ca/Destinations-In-Orange-County.d553248635083901431.Hotel-Destinations)[Vacation Rentals in Orange County](https://expedia.ca/Destinations-In-Orange-County.d553248635083901431.Vacation-Rental-Destinations)[Orange County Car Rentals](https://expedia.ca/Destinations-In-Orange-County.d553248635083901431.Car-Rental-Destinations)[Orange County Vacations](https://expedia.ca/Orange-County.d553248635083901431.Destination-Travel-Guides) ![West Point Cadet Chapel, in upstate NY - open to the public daily - tours offered - beautiful!! ](https://images.trvl-media.com/place/9700/a15e9f8e-9431-4121-965f-6fb3d703bf4e.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by crissibeth # Orange 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 Orange County ![Newburgh showing a marina and boating](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/59000/59968-Newburgh-And-Vicinity.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Newburgh [](https://expedia.ca/Newburgh-Hotels-Hotel-With-Pool.0-0-d6023343-tHotelwithPool.Travel-Guide-Filter-Hotels) ![](https://mediaim.expedia.com/destination/2/b3592d5854c5ebf058517b7fb1df474d.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Middletown [](https://expedia.ca/Middletown-Hotels-Hotel-With-Pool.0-0-d8864-tHotelwithPool.Travel-Guide-Filter-Hotels) ![](https://mediaim.expedia.com/destination/2/b3592d5854c5ebf058517b7fb1df474d.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Goshen [](https://expedia.ca/Goshen-Hotels-Hotel-With-Pool.0-0-d8005-tHotelwithPool.Travel-Guide-Filter-Hotels) ## Check availability on Orange County Hotels with a Pool Tonight [Dec 8 - Dec 9](https://www.expedia.ca/Hotel-Search?regionId=553248635083901431&startDate=2025-12-08&endDate=2025-12-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 9 - Dec 10](https://www.expedia.ca/Hotel-Search?regionId=553248635083901431&startDate=2025-12-09&endDate=2025-12-10&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635083901431&startDate=2025-12-12&endDate=2025-12-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635083901431&startDate=2025-12-19&endDate=2025-12-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Orange 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-Orange-County-Hotel-With-Pool.0-0-d553248635083901431-tHotelwithPool.Hotel-Filter-Destinations)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Orange-County-Hotel-With-Pool.0-0-d553248635083901431-tHotelwithPool.Hotel-Filter-Destinations) ## Top Orange County Hotel Reviews ![The Thayer Hotel at West Point](https://images.trvl-media.com/lodging/6000000/5800000/5792300/5792279/c0c1b35f_y.jpg) ### The Thayer Hotel at West Point 10/10 Excellent "Well renovated, well-maintained historical and charming hotel right on campus of West Point. Staff were helpful, & each room featured a different veteran’s biography. Overlooks the Hudson River. On site restaurant. We greatly enjoyed our stay." [](https://expedia.ca/Newburgh-Hotels-Thayer-Hotel.h5792279.Hotel-Information) ![Hampton Inn by Hilton Middletown](https://images.trvl-media.com/lodging/1000000/290000/282000/281932/8c9a3fbd_y.jpg) ### Hampton Inn by Hilton Middletown 10/10 Excellent "Great kind staff and clean facility. The staff really take pride in what they do. Would highly recommend!" [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-By-Hilton-Middletown.h281932.Hotel-Information) ![Howard Johnson by Wyndham Newburgh/West Point](https://images.trvl-media.com/lodging/1000000/10000/7700/7652/8a35f36a_y.jpg) ### Howard Johnson by Wyndham Newburgh/West Point 10/10 Excellent "Excellent " [](https://expedia.ca/Newburgh-Hotels-Howard-Johnson-By-Wyndham-NewburghWest-Point.h7652.Hotel-Information) ![Overlook Lodge at Bear Mountain](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/670b74a6_y.jpg) ### Overlook Lodge at Bear Mountain 10/10 Excellent "Staff was incredibly kind and the room was super cozy. The inn is beautiful and there is enough to do around. " [](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![Hampton Inn Harriman Woodbury](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/c7d384a9_y.jpg) ### Hampton Inn Harriman Woodbury 10/10 Excellent "Staff great room very clean " [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ![Sleep Inn & Suites Monroe - Woodbury](https://images.trvl-media.com/lodging/21000000/20600000/20597600/20597588/0db56af9_y.jpg) ### Sleep Inn & Suites Monroe - Woodbury 10/10 Excellent "Yes" [](https://expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Monroe-Woodbury.h20597588.Hotel-Information) ![Holiday Inn Express & Suites Montgomery by IHG](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/98944f60_y.jpg) ### Holiday Inn Express & Suites Montgomery by IHG 10/10 Excellent "Room was clean a d spacious. Staff courteous and helpful." [](https://expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Suites-Montgomery.h7814618.Hotel-Information) ![Sleep Inn & Suites Middletown - Goshen](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/1b0779e7_y.jpg) ### Sleep Inn & Suites Middletown - Goshen 10/10 Excellent "The stay was excellent. The pool was a perfect temp for all to unwind after a long drive. We enjoyed the breakfast. The staff was very friendly and helpful. " [](https://expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information) ![Holiday Inn Express Hotel & Suites Chester by IHG](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/02f3df9e_y.jpg) ### Holiday Inn Express Hotel & Suites Chester by IHG 10/10 Excellent "Great , no complaints. 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