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 30 - Mar 31](https://www.expedia.com/Hotel-Search?regionId=10021&startDate=2026-03-30&endDate=2026-03-31&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 31 - Apr 1](https://www.expedia.com/Hotel-Search?regionId=10021&startDate=2026-03-31&endDate=2026-04-01&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This 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) Next weekend [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) ![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) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/6b6d035b.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 (1,004 reviews) "Superb place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Denessy $99 nightly $112 total Mar 31 - Apr 1 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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1770000/1764800/1764709/0e18f638.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) ### Homewood Suites Stewart Airport [](https://www.expedia.com/Newburgh-Hotels-Homewood-Suites-Stewart-Airport.h1764709.Hotel-Information) New Windsor 9.2/10 Wonderful (1,003 reviews) "Staff (particularly Kathleen) was lovely " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abby $145 nightly $164 total Apr 6 - Apr 7 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) ![Reception](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/679bdd4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/7384700a.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) ### 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 (1,002 reviews) "Great staff and clean rooms. Beautiful views." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Renee $97 nightly $110 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 6 - Apr 7 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) ![Property amenity](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/ba2c672f.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) ### Courtyard by Marriott Middletown Goshen [](https://www.expedia.com/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.Hotel-Information) Middletown 8.6/10 Excellent (1,002 reviews) "Great stay!!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) diana $105 nightly $125 total Apr 26 - Apr 27 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.Hotel-Information) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/290000/282000/281932/cf710d60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/290000/282000/281932/88d2ecc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/290000/282000/281932/8c9a3fbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/290000/282000/281932/d055a3f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn by Hilton Middletown [](https://www.expedia.com/Newburgh-Hotels-Hampton-Inn-By-Hilton-Middletown.h281932.Hotel-Information) Middletown 8.6/10 Excellent (1,000 reviews) "It was a beautiful experience. Clean and 5 star service. The staff so friendly and helpful. Peaceful fun experience. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda $92 nightly $108 total Apr 14 - Apr 15 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Hampton-Inn-By-Hilton-Middletown.h281932.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/71000000/70420000/70415100/70415091/814578fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/71000000/70420000/70415100/70415091/67107f0f.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 $459 nightly $541 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, sun loungers](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/64788546.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) ![Reception](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/2d8c93f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/8648b91b.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 (1,007 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 $121 nightly $143 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/111000000/110790000/110784600/110784547/320bd4a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110790000/110784600/110784547/be0aeba4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110790000/110784600/110784547/c06f2598.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, towels, soap, toilet paper](https://images.trvl-media.com/lodging/111000000/110790000/110784600/110784547/2a0deaa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 1-bedroom apartment in Carmel with WiFi, AC [](https://www.expedia.com/Carmel-Hotels-Charming-1-Bedroom-Apartment-In-Carmel-With-WiFi.h110784547.Hotel-Information) Carmel Hamlet 9.0/10 Wonderful (2 reviews) "Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emmett $257 nightly $279 total Mar 31 - Apr 1 Total with taxes and fees [](https://www.expedia.com/Carmel-Hotels-Charming-1-Bedroom-Apartment-In-Carmel-With-WiFi.h110784547.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 (1,006 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 $135 nightly $152 total Apr 29 - Apr 30 Total with taxes and fees [](https://www.expedia.com/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.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=2026-04-13&endDate=2026-04-14®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 ![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 "My stay was enjoyable. My family and I were comfortable. Parking can be a bit busy " [](https://expedia.com/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.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 4/10 Poor "Clean room house keeping ladies were and is an amazing staff, nice hotel but key cards didn’t work and checking out girl was terrible front desk deanna I think her name she was inhospitable , she’s rude doesn’t know how to talk to people I guess that’s why she doesn’t answer the phones and noncompliant when we ask about late checkout her answer was no we busy full !!! , the breakfast was terrible, the noise from the highway and the next door slamming the door our room shook I pay one night for a business meeting that was delayed a bit and we asked for a couple more hours and was turned down . I’m glad because we won’t be going back!!" [](https://expedia.com/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) ![Courtyard by Marriott Poughkeepsie](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/990080f2_y.jpg) ### Courtyard by Marriott Poughkeepsie 10/10 Excellent "Hotel was very clean and check in and out was quick and effecient. Compimentary breakfast or at least coffee would have been nice, as most similar hotels offer. Also the bar did not open til 6pm....we would have liked to have had a cocktail when we checked in at 4 or 5 prior to leaving for the function we had to go to. Overall very nice hotel." [](https://expedia.com/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.Hotel-Information) ![Inn on the Hudson](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148858/b1419d47_y.jpg) ### Inn on the Hudson 2/10 Terrible "It was dirty (since had old toothpaste still in it, toilet had hairs on it, bed smelled of a woman's perfume). No comfortable, just two old sheets with a fleece blanket in between. I reserved it for 3 nights and left after 1\. When checking out, the receptionist immediately gave us the Expedia contact number indicating this often happens. It was gross. I felt bad having my wife stay here. I'm OK with old; but there's no excuse for dirty/unclean." [](https://expedia.com/White-Plains-Hotels-Inn-On-The-Hudson.h1148858.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 "Very nice environment, staff was pleasant, and breakfast was delicious!!" [](https://expedia.com/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.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 "Great breakfast buffet" [](https://expedia.com/Newburgh-Hotels-Homewood-Suites-Stewart-Airport.h1764709.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 "The staff was very courteous & friendly. The room was clean & the breakfast menu was great serving different options every morning. We will stay here again the next time we are in New Paltz." [](https://expedia.com/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.Hotel-Information) ![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) ![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) ## 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) - 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