Title: Book the Best Hotels with POOL in New Windsor in 2025 | Expedia.ca [Hotels in New Windsor](https://expedia.ca/New-Windsor-Hotels.d10021.Travel-Guide-Hotels)[Vacation Rentals in New Windsor](https://expedia.ca/New-Windsor-Vacation-Rentals.d10021.Travel-Guide-VacationRentals)[Things to do in New Windsor](https://expedia.ca/Things-To-Do-In-New-Windsor.d10021.Travel-Guide-Activities)[New Windsor Car Rentals](https://expedia.ca/Car-Rentals-In-New-Windsor.d10021.Car-Rental-Guide)[New Windsor Vacation Packages](https://expedia.ca/New-Windsor.d10021.Destination-Travel-Guides) ![Gloomy cloud over Storm King sunset. Landscape architecture juxtaposed in the Northeast's Autumn. #GoldenHour](https://images.trvl-media.com/place/6148010/b4469cf7-6c52-4383-a18b-1573522aca84.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Wanderlustfemale # Find Hotels with a Pool in New Windsor, NY from CA $130 - ![](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 ## Check availability on New Windsor Hotels with a Pool Tonight [Nov 21 - Nov 22](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2025-11-21&endDate=2025-11-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 22 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2025-11-22&endDate=2025-11-23&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2025-11-21&endDate=2025-11-23&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2025-11-28&endDate=2025-11-30&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top New Windsor Hotels with a Pool ![Indoor pool](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/e8f6eb1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/1047d873.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Accessible, Non Smoking](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/38401260.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/51570973.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point New Windsor 8.4/10 Very good (1008) "Fast check in, great parking area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Helene [](https://www.expedia.ca/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) ![Blackout drapes, iron/ironing board, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/2000000/1770000/1764800/1764709/771d3275.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1770000/1764800/1764709/945aae91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites Stewart Airport New Windsor 9.2/10 Wonderful (1000) "We’ve stayed here once before and the service continues to be excellent. Breakfast buffet is great, staff is friendly and the rooms are clean and comfortable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $179 CA $202 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Newburgh-Hotels-Homewood-Suites-Stewart-Airport.h1764709.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/71000000/70420000/70415100/70415091/2396df2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/71000000/70420000/70415100/70415091/a7704166.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/71000000/70420000/70415100/70415091/6da85435.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/71000000/70420000/70415100/70415091/5555dde6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### LEGOLAND Hotel NEW York Goshen 8.6/10 Excellent (22) "We loved everything from the staff to the stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Arnassia CA $158 CA $357 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Goshen-Hotels-LEGOLAND-Hotel-NEW-York.h70415091.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/a79c4292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/b02bdf9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/56f73483.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Accessible, Non Smoking](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/47fa2e85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Poughkeepsie Crown Heights 8.8/10 Excellent (1000) "Everything about this hotel was great would absolutely stay again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda CA $139 CA $162 total includes taxes & fees Nov 29 - Nov 30 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.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/2000000/1200000/1194400/1194365/92dbf0a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/02f3df9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Chester by IHG Chester 8.4/10 Very good (1001) "Great for a quick stay 👍" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jerry CA $110 CA $130 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) ![Sports facility](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/2f2f704a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/459515b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/239951b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/e1e7e350.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Fishkill Fishkill 8.6/10 Excellent (1003) "It was a great place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda CA $133 CA $150 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hilton-Garden-Inn-Fishkill.h890436.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/35000000/34330000/34323400/34323334/5883f255.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snack bar](https://images.trvl-media.com/lodging/35000000/34330000/34323400/34323334/cb9fb634.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34330000/34323400/34323334/0368b452.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34330000/34323400/34323334/9adcfc3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites by Hilton Poughkeepsie Poughkeepsie 9.6/10 Exceptional (1002) "Rooms were clean, comfortable and spacious." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MARIA CA $145 CA $168 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Poughkeepsie-Hotels-Homewood-Suites-By-Hilton-Poughkeepsie.h34323334.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) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/bdaa6450.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) ![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 New Paltz 9.4/10 Exceptional (1004) "Clean, comfortable, wonderful staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicole CA $156 CA $175 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.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) ![Room, 1 Queen Bed, Non Smoking (Stone Cottages at Bear Mountain)](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/42067525.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/4000000/3430000/3425800/3425772/314aa890.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Overlook Lodge at Bear Mountain Bear Mountain 8.4/10 Very good (1011) "Parking was very easy, beautiful area, very nice staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth CA $145 CA $165 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/4100/4098/0a5108cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4100/4098/77a42b8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/4100/4098/633769f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/10000/4100/4098/fed7909a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Middletown-Goshen Middletown 9.4/10 Exceptional (916) "great staff, clean rooms, nice breakfast .. overall a pleasant & safe atmosphere !" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emerson CA $154 CA $182 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Middletown-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Middletown.h4098.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.ca/Hotel-Search?startDate=2025-12-05&endDate=2025-12-06®ionId=10021&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AFFINITY_BF_PROMO_10021) ## Top New Windsor Hotel Reviews ![Americas Best Value Inn New Paltz](https://images.trvl-media.com/lodging/1000000/900000/897900/897882/1c07aec9_y.jpg) ### Americas Best Value Inn New Paltz 10/10 Excellent "Excellent ! " [](https://expedia.ca/Poughkeepsie-Hotels-Americas-Best-Value-Inn-New-Paltz.h897882.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 "Great experience highly recommend. " [](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.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 for a quick stay 👍" [](https://expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.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 "Clean room" [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ![Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/e8f6eb1b_y.jpg) ### Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point 10/10 Excellent "Never stayed at a Red Roof before. I was pleasantly surprise. Had a good night sleep and hot shower. The people at the front desk were very helpful and friendly. " [](https://expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ![Hampton Inn & Suites Poughkeepsie](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/47fa2e85_y.jpg) ### Hampton Inn & Suites Poughkeepsie 10/10 Excellent "Easy che kin nice, newly refurbished rooms. " [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information) ![Hampton Inn by Hilton New Paltz](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/bd59d6cb_y.jpg) ### Hampton Inn by Hilton New Paltz 10/10 Excellent "Rooms were clean and comfortable, breakfast was good for everyone" [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.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 "Best hotel I’ve stayed in for a while. Very clean, friendly staff, very comfortable. Walking distance to everything. Breakfast was excellent. We stayed 5 nights and breakfast was different every day…. Fried eggs, scramble, omelet, sausage, bacon, empanadas, waffles, it was excellent!" [](https://expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information) ![The Crossroads Hotel, Newburgh](https://images.trvl-media.com/lodging/1000000/20000/14500/14410/5440914b_y.jpg) ### The Crossroads Hotel, Newburgh 10/10 Excellent "Everything " [](https://expedia.ca/Newburgh-Hotels-The-Crossroads-Hotel.h14410.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in New Windsor? > [Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point](https://www.expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information): Features free self parking, an indoor pool, and complimentary wireless internet access. [Homewood Suites Stewart Airport](https://www.expedia.ca/Newburgh-Hotels-Homewood-Suites-Stewart-Airport.h1764709.Hotel-Information): Offers buffet, an indoor pool, and complimentary wired internet access. [Hampton Inn & Suites Poughkeepsie](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information): Provides a snack bar/deli, an indoor pool, and buffet. [Hampton Inn Harriman Woodbury](https://www.expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information): Hotel, 1-minute walk from Woodbury Common Premium Outlets. Features daily, an indoor pool, and complimentary wired internet access. [Overlook Lodge at Bear Mountain](https://www.expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information): Hotel, 1-minute walk from Bear Mountain State Park. Offers a full-service spa, a seasonal outdoor pool, and a snack bar/deli. ### What is there to see and do in New Windsor? > Make a point to visit attractions like Lake Tiorati Beach and Ice Time Sports Complex. Discover sights such as New Windsor Cantonment State Historic Site, National Purple Heart Hall of Honor, and Knox's Headquarters State Historic Site during your stay. Travelers love New Windsor for its array of dining options. ### When is the best time to book a hotel with a pool in New Windsor? > You may want to think about an accommodation that has an outdoor pool if you're planning to visit New Windsor in the warmest months of July, August, or June when the average temperature is 69°F. 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