Title: Highly Rated Hotels With Pool in New Windsor | Expedia.com [New Windsor Travel Guide](https://expedia.com/New-Windsor.dx10021)[Hotels in New Windsor](https://expedia.com/New-Windsor-Hotels.d10021.Travel-Guide-Hotels)[Vacation Rentals in New Windsor](https://expedia.com/New-Windsor-Vacation-Rentals.d10021.Travel-Guide-VacationRentals)[Flights to New Windsor](https://expedia.com/Cheap-Flights-To-New-Windsor.d10021.Travel-Guide-Flights)[Things to do in New Windsor](https://expedia.com/Things-To-Do-In-New-Windsor.d10021.Travel-Guide-Activities)[Car Rentals in New Windsor](https://expedia.com/Car-Rentals-In-New-Windsor.d10021.Car-Rental-Guide)[New Windsor Vacation Packages](https://expedia.com/New-Windsor.d10021.Destination-Travel-Guides) ![](https://images.trvl-media.com/place/6148010/b4469cf7-6c52-4383-a18b-1573522aca84.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Wanderlustfemale ![](https://images.trvl-media.com/place/6148010/b4469cf7-6c52-4383-a18b-1573522aca84.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Upfront pricing Our total price for your stay includes taxes and fees - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save 10% or more on over 100,000 hotels worldwide with Member Prices [Learn about One Key](https://www.expedia.com/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on New Windsor Hotels with a Pool Tonight [Mar 28 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=10021&startDate=2026-03-28&endDate=2026-03-29&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 29 - Mar 30](https://www.expedia.com/Hotel-Search?regionId=10021&startDate=2026-03-29&endDate=2026-03-30&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=10021&startDate=2026-04-03&endDate=2026-04-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=10021&startDate=2026-04-10&endDate=2026-04-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for New Windsor hotels with a pool ![Indoor pool](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/38c7288e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/6b6d035b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Check-in/check-out kiosk](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/cabaefdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 2 Queen Beds, Non Smoking, Lake View | Desk, iron/ironing board, free cribs/infant beds, rollaway beds](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/ae84ea2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point [](https://www.expedia.com/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) New Windsor 8.4/10 Very Good (1,000 reviews) "Superb place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Denessy $99 nightly $112 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1770000/1764800/1764709/e9b6c0b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1770000/1764800/1764709/945aae91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1770000/1764800/1764709/d07e2b65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business center](https://images.trvl-media.com/lodging/2000000/1770000/1764800/1764709/d51e63c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites Stewart Airport [](https://www.expedia.com/Newburgh-Hotels-Homewood-Suites-Stewart-Airport.h1764709.Hotel-Information) New Windsor 9.2/10 Wonderful (1,002 reviews) "Staff (particularly Kathleen) was lovely " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abby $147 nightly $166 total Apr 4 - Apr 5 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Homewood-Suites-Stewart-Airport.h1764709.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/383ffb6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/13890846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/8626bd92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/679bdd4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Overlook Lodge at Bear Mountain [](https://www.expedia.com/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) Bear Mountain 8.4/10 Very Good (1,001 reviews) "Great staff and clean rooms. Beautiful views." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Renee $99 nightly $113 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/2000000/1220000/1214400/1214332/d2d7994a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1220000/1214400/1214332/c4928040.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1220000/1214400/1214332/w4000h2662x0y0-aa463bc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1220000/1214400/1214332/5b25316b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Goshen Middletown [](https://www.expedia.com/Newburgh-Hotels-Fairfield-Inn-Suites-By-Marriott-Goshen-Middletown.h1214332.Hotel-Information) Goshen 8.8/10 Excellent (1,000 reviews) "Amazing staff Great breakfast Clean quiet rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) R $110 nightly $135 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Fairfield-Inn-Suites-By-Marriott-Goshen-Middletown.h1214332.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/fb63b6d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/5a64b5a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/0bd48f86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/ba2c672f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Middletown Goshen [](https://www.expedia.com/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.Hotel-Information) Middletown 8.6/10 Excellent (1,001 reviews) "Great stay!!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) diana $93 nightly $109 total Apr 2 - Apr 3 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/71000000/70420000/70415100/70415091/73a2acb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/71000000/70420000/70415100/70415091/ded4c5f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/71000000/70420000/70415100/70415091/814578fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ninjago Premium Themed | Desk, laptop workspace, free WiFi, bed sheets](https://images.trvl-media.com/lodging/71000000/70420000/70415100/70415091/aaa826cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### LEGOLAND Hotel NEW York [](https://www.expedia.com/Goshen-Hotels-LEGOLAND-Hotel-NEW-York.h70415091.Hotel-Information) Goshen 8.8/10 Excellent (38 reviews) "Room very clean, breakfast was great, staff were soo kind!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mercedes $427 nightly $504 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Goshen-Hotels-LEGOLAND-Hotel-NEW-York.h70415091.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/bd59d6cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/7df797b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/00367844.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/a9b4d40a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn by Hilton New Paltz [](https://www.expedia.com/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.Hotel-Information) New Paltz 9.4/10 Exceptional (1,003 reviews) "The service is excellent and the room is very clean" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wai Peng $139 nightly $155 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/40a70d08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/e0fcb0f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One King Bed Studio | Living area | 55-inch LCD TV with cable channels, TV, pay movies](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/7a9acd26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/9631af0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Harriman Woodbury [](https://www.expedia.com/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) Central Valley 9.2/10 Wonderful (1,078 reviews) "Hotel was very clean and well maintained " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephen $106 nightly $130 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/117000000/116370000/116362400/116362325/e25829b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116370000/116362400/116362325/8d663c7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116370000/116362400/116362325/1ae526bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/117000000/116370000/116362400/116362325/1616e5db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Cabin with Pool & Fire Pit [](https://www.expedia.com/Montgomery-Hotels-Cozy-Cabin-Gateway-I-15-Acres-W-Pool-Firepit.h116362325.Hotel-Information) Montgomery 10/10 Exceptional (3 reviews) "This little cabin was exactly what we needed for our stay in NY. It looks just as described, was clean, and the location was perfect for all of the places we wanted to visit. Overall it was very cozy and relaxing and we can't wait to stay again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah A. $182 nightly $205 total Mar 30 - Mar 31 Total with taxes and fees [](https://www.expedia.com/Montgomery-Hotels-Cozy-Cabin-Gateway-I-15-Acres-W-Pool-Firepit.h116362325.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/64788546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/1a5890e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/2d8c93f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/308be1ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Chester by IHG [](https://www.expedia.com/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) Chester 8.6/10 Excellent (1,003 reviews) "We have been several times during the past few years the hotel is in very good condition and the coffee is really good available 24 hours a day the breakfast has several choices that are good the rooms are clean the A/C and heat work great overall great place to stay we come sometimes for a quick weekend getaway from New York City will continue to come back. Great local diner and restaurants." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kenneth $105 nightly $124 total Apr 1 - Apr 2 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.com/Hotel-Search?startDate=2026-04-11&endDate=2026-04-12®ionId=10021&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in New Windsor Breakfast included Hot tub 4 stars 5 stars Spa ## Top New Windsor Hotel Reviews ![Hampton Inn & Suites Poughkeepsie](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/ee108dad_y.jpg) ### Hampton Inn & Suites Poughkeepsie 4/10 Poor "The breakfast menu was fresh and the coffee at all times was a nice perk. The staff at checkout was rude and even though we had asked for adjoining rooms, we were not provided that at check in. We were instead given rooms on opposite floors. There was something spilled on the side table and something on the bottom of the bathroom door. " [](https://expedia.com/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information) ![Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/38c7288e_y.jpg) ### Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point 8/10 Good "Convenient, clean and friendly.. " [](https://expedia.com/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ![Courtyard by Marriott Poughkeepsie](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/990080f2_y.jpg) ### Courtyard by Marriott Poughkeepsie 8/10 Good "NA" [](https://expedia.com/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.Hotel-Information) ![Hampton Inn by Hilton New Paltz](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/dab27d3b_y.jpg) ### Hampton Inn by Hilton New Paltz 10/10 Excellent "Loved the breakfast, different items each day. Also, the bed was so comfortable! " [](https://expedia.com/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.Hotel-Information) ![Overlook Lodge at Bear Mountain](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/679bdd4c_y.jpg) ### Overlook Lodge at Bear Mountain 10/10 Excellent "Very good experience " [](https://expedia.com/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![Homewood Suites Stewart Airport](https://images.trvl-media.com/lodging/2000000/1770000/1764800/1764709/e9b6c0b3_y.jpg) ### Homewood Suites Stewart Airport 10/10 Excellent "Lovely front desk staff (Kathy), excellent breakfast!" [](https://expedia.com/Newburgh-Hotels-Homewood-Suites-Stewart-Airport.h1764709.Hotel-Information) ![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 "Very clean " [](https://expedia.com/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.Hotel-Information) ![Inn on the Hudson](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148858/b1419d47_y.jpg) ### Inn on the Hudson 4/10 Poor "When you walk in and there are ear plugs on the desk, you get an idea of the state of the property. It was a rough stay. " [](https://expedia.com/White-Plains-Hotels-Inn-On-The-Hudson.h1148858.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 8/10 Good "Parking was easy- lady at the front desk was great. Room was good " [](https://expedia.com/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in New Windsor? ### What is there to see and do in New Windsor? ### When is the best time to book a hotel with a pool in New Windsor? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [New York Hotels ](https://www.expedia.com/New-York-Hotels.d178293.Travel-Guide-Hotels) - [Hotels near Motorcyclepedia Museum ](https://www.expedia.com/Motorcyclepedia-Museum-Hotels.0-l553248621532664656-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Newburgh ](https://www.expedia.com/Newburgh-Hotels-Cheap-Hotels.0-0-d6023343-tCheapHotels.Travel-Guide-Filter-Hotels) - [Newburgh Hotels ](https://www.expedia.com/Newburgh-Hotels.d6023343.Travel-Guide-Hotels) - [Luxury Hotels in Newburgh ](https://www.expedia.com/Newburgh-Hotels-Luxury-Hotel.0-0-d6023343-tLuxuryHotel.Travel-Guide-Filter-Hotels) - 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