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 ![](https://images.trvl-media.com/place/9700/a15e9f8e-9431-4121-965f-6fb3d703bf4e.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 ![Route 17 in ny is a great road to view the fall foliage](https://images.trvl-media.com/place/8005/8b2c54c4-af30-4521-9b56-3bdf0a8d1a15.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) ![Newburgh showing a marina and boating](https://images.trvl-media.com/place/6023343/45f8df4a-bc8f-41a1-ab60-8fd59fcf5c7d.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) ![the Millrace](https://images.trvl-media.com/place/8005/3b1c0b95-e385-4e17-84fb-ec95384bb3c1.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) ![Pittsford, NY, USA - 02-01-2025: Winter afternoon aerial photo of the Village of Pittsford four corners with snow on the ground. ](https://images.trvl-media.com/place/6171715/3531be1f-15d9-4b32-ba1e-4f29805eb228.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Monroe [](https://expedia.ca/Monroe-Hotels-Hotel-With-Pool.0-0-d6171715-tHotelwithPool.Travel-Guide-Filter-Hotels) ![Hudson River and the Hudson Highlands from New Windsor, New York](https://images.trvl-media.com/place/10021/c7e47857-5297-4fca-a2da-20a9979aa9f1.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### New Windsor [](https://expedia.ca/New-Windsor-Hotels-Hotel-With-Pool.0-0-d10021-tHotelwithPool.Travel-Guide-Filter-Hotels) ![George W. Perkins Memorial Drive with Hudson River and Bear Mountain Bridge, NY](https://images.trvl-media.com/place/183639/985ee9c0-c331-4997-9abd-dfd80d6d3cf2.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Bear Mountain [](https://expedia.ca/Bear-Mountain-Hotels-Hotel-With-Pool.0-0-d183639-tHotelwithPool.Travel-Guide-Filter-Hotels) ![Hudson Valley Grass Fed Beef Farm Silos](https://images.trvl-media.com/place/8728/4b97bae2-8d0c-44a5-85ba-ea005576c5a5.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Montgomery [](https://expedia.ca/Montgomery-Hotels-Hotel-With-Pool.0-0-d8728-tHotelwithPool.Travel-Guide-Filter-Hotels) ## Check availability on Orange County Hotels with a Pool Tonight [Mar 10 - Mar 11](https://www.expedia.ca/Hotel-Search?regionId=553248635083901431&startDate=2026-03-10&endDate=2026-03-11&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 11 - Mar 12](https://www.expedia.ca/Hotel-Search?regionId=553248635083901431&startDate=2026-03-11&endDate=2026-03-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=553248635083901431&startDate=2026-03-13&endDate=2026-03-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=553248635083901431&startDate=2026-03-20&endDate=2026-03-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AFFINITY_SPRING_PROMO_553248635083901431) ![](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 ![Courtyard by Marriott Middletown Goshen](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/5a64b5a6_y.jpg) ### Courtyard by Marriott Middletown Goshen 10/10 Excellent "Great stay!!! " [](https://expedia.ca/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.Hotel-Information) ![Tru by Hilton Middletown](https://images.trvl-media.com/lodging/37000000/36250000/36247800/36247736/ea33701a_y.jpg) ### Tru by Hilton Middletown 10/10 Excellent "Beautiful, new and clean!!" [](https://expedia.ca/Newburgh-Hotels-Tru-By-Hilton-Middletown.h36247736.Hotel-Information) ![Hampton Inn & Suites Newburgh Stewart Airport](https://images.trvl-media.com/lodging/18000000/17270000/17262200/17262186/3df08b3c_y.jpg) ### Hampton Inn & Suites Newburgh Stewart Airport 10/10 Excellent "Wonderful accommodations!!" [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-Suites-Newburgh-Stewart-Airport.h17262186.Hotel-Information) ![Holiday Inn Express Hotel & Suites Chester by IHG](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/8648b91b_y.jpg) ### Holiday Inn Express Hotel & Suites Chester by IHG 10/10 Excellent "Excellent location of hotel. The room was clean (no issues). From check-in to check out the staff was accommodating, courteous, friendly & helpful. Wi-Fi connected efficiently and breakfast was good. I believe guests would be satisfied staying at the hotel." [](https://expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) ![Courtyard by Marriott Newburgh Stewart Airport](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/7494afa4_y.jpg) ### Courtyard by Marriott Newburgh Stewart Airport 10/10 Excellent "The room was very clean and spacious. This is one of the main reasons that I love booking at this location" [](https://expedia.ca/Newburgh-Hotels-Courtyard-By-Marriott-Newburgh-Stewart-Airport.h42673.Hotel-Information) ![Hampton Inn Harriman Woodbury](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/e0fcb0f3_y.jpg) ### Hampton Inn Harriman Woodbury 6/10 Okay "Hotel is a bit dated, king size bed was hard, didn’t sleep well. " [](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/de7f38a7_y.jpg) ### Sleep Inn & Suites Monroe - Woodbury 10/10 Excellent "Clean and great staff" [](https://expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Monroe-Woodbury.h20597588.Hotel-Information) ![Sleep Inn & Suites Middletown - Goshen](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/aeade474_y.jpg) ### Sleep Inn & Suites Middletown - Goshen 10/10 Excellent "Hotel was in a good location for our needs. Staff is friendly and helpful. We would recommend. " [](https://expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information) ![Hampton Inn by Hilton Middletown](https://images.trvl-media.com/lodging/1000000/290000/282000/281932/88d2ecc5_y.jpg) ### Hampton Inn by Hilton Middletown 8/10 Good "Room was comfortable temperature wise" [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-By-Hilton-Middletown.h281932.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - More ways to book - [Cheap Hotels in Campbell Hall ](https://www.expedia.ca/Campbell-Hall-Hotels-Cheap-Hotels.0-0-d6338665-tCheapHotels.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Central New York City ](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Adults-Only-Resorts.0-n553248633938969338-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Central New York City ](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Beach-Hotel.0-n553248633938969338-0-tBeachHotel.Travel-Guide-Filter-Hotels) - 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