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) ![](https://mediaim.expedia.com/destination/2/6747dae34f8ec5459e58210202f4caed.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Wanderlustfemale # Find Hotels with a Pool in New Windsor, NY from CA $155 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [Oct 6 - Oct 7](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2025-10-06&endDate=2025-10-07&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 7 - Oct 8](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2025-10-07&endDate=2025-10-08&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2025-10-10&endDate=2025-10-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top New Windsor Hotels with a Pool ![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/2000000/1200000/1194400/1194365/09941fc6.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 (1004) "Everything was amazing! Thank You for a great stay. " CA $169 CA $199 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.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/c7d384a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/6459dee3.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 Central Valley 9.2/10 Wonderful (1006) "Great place to stay, very clean and conveniently located" CA $165 CA $203 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/02e6ff39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/1b0779e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/747581be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/cefa7296.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Inn & Suites Middletown - Goshen Middletown 8.4/10 Very good (1010) "great stay" CA $146 CA $173 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/e8f6eb1b.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) ![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/1000000/880000/875700/875625/6b6d035b.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 (1005) "Great price for a great hotel" CA $137 CA $155 total includes taxes & fees Oct 7 - Oct 8 [](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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1770000/1764800/1764709/0e18f638.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites Stewart Airport New Windsor 9.2/10 Wonderful (1001) "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." CA $224 CA $254 total includes taxes & fees Oct 26 - Oct 27 [](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) ![Children's play area - indoor](https://images.trvl-media.com/lodging/71000000/70420000/70415100/70415091/9834d0ca.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) ### LEGOLAND Hotel NEW York Goshen 8.4/10 Very good (10) "They made the place so much fun for children and every staff member was beyond helpful and cheerful. Truly a great family place. " CA $268 CA $375 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Goshen-Hotels-LEGOLAND-Hotel-NEW-York.h70415091.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) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/4100/4098/d1fd54a7.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) ![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) ### La Quinta Inn & Suites by Wyndham Middletown-Goshen Middletown 9.4/10 Exceptional (851) "Place was great have stayed here many times." CA $177 CA $209 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Middletown-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Middletown.h4098.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/2000000/1220000/1214400/1214332/067fc37c.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) ![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 Goshen 8.8/10 Excellent (1001) "Great place to stay when you’re in need of relaxation and some family time!" CA $130 CA $160 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Newburgh-Hotels-Fairfield-Inn-Suites-By-Marriott-Goshen-Middletown.h1214332.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/23000000/22940000/22934500/22934426/202f6398.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee service](https://images.trvl-media.com/lodging/23000000/22940000/22934500/22934426/c86c7344.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/23000000/22940000/22934500/22934426/78ebeb9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/23000000/22940000/22934500/22934426/c329caee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Suites Fishkill near Interstate 84 Fishkill 9.2/10 Wonderful (1000) "The area around the hotel is fine with a diner within walking distance. Very convenient location to Beacon, and highway I-84. Hotel's conditions are excellent and clean." CA $166 CA $188 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Poughkeepsie-Hotels-Comfort-Suites-Fishkill-Near-Interstate-84.h22934426.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/c695ef3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 1 King Bed, Accessible (Hearing)](https://images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/4eb66254.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/130ec357.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/7472348e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites By Hilton Poughkeepsie Poughkeepsie 9.4/10 Exceptional (341) "A great location. " CA $155 CA $180 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Poughkeepsie-Hotels-Home2-Suites-By-Hilton-Poughkeepsie.h103394153.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=2025-10-20&endDate=2025-10-21®ionId=10021&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top New Windsor Hotel Reviews ![Holiday Inn Express Poughkeepsie by IHG](//images.trvl-media.com/lodging/1000000/20000/12200/12157/9d729415_y.jpg) ### Holiday Inn Express Poughkeepsie by IHG 10/10 Excellent "This place has one of the best showers! The water pressure is almost like getting power washed. My husband loved it! Convient to Main St Poughkeepsie for dining options." [](https://expedia.ca/Poughkeepsie-Hotels-Holiday-Inn-Express-Poughkeepsie.h12157.Hotel-Information) ![Sleep Inn & Suites Middletown - Goshen](//images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/1b0779e7_y.jpg) ### Sleep Inn & Suites Middletown - Goshen 10/10 Excellent "Hreat" [](https://expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information) ![Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point](//images.trvl-media.com/lodging/1000000/880000/875700/875625/e8f6eb1b_y.jpg) ### Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point 10/10 Excellent "T" [](https://expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ![Hampton Inn by Hilton New Paltz](//images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/bd59d6cb_y.jpg) ### Hampton Inn by Hilton New Paltz 10/10 Excellent "Friendly staff, clean rooms. Could use better seating." [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.Hotel-Information) ![Hampton Inn & Suites Poughkeepsie](//images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/47fa2e85_y.jpg) ### Hampton Inn & Suites Poughkeepsie 10/10 Excellent "The room was spacious, clean, and comfortable. There is direct TV available for entertainment. Breakfast was nice. The presence of a pool and hot tub is great too. This hotel accepts dogs and cats 50 lbs and under with additional fee." [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information) ![Americas Best Value Inn New Paltz](//images.trvl-media.com/lodging/1000000/900000/897900/897882/1c07aec9_y.jpg) ### Americas Best Value Inn New Paltz 10/10 Excellent "When it comes to a pleasant surprise, this was definitely IT! Clean, comfortable, inexpensive, friendly, renovated, and (did I mention) inexpensive!?? Adorable little breakfast area with complimentary breakfast foods as well. " [](https://expedia.ca/Poughkeepsie-Hotels-Americas-Best-Value-Inn-New-Paltz.h897882.Hotel-Information) ![Homewood Suites Stewart Airport](//images.trvl-media.com/lodging/2000000/1770000/1764800/1764709/771d3275_y.jpg) ### Homewood Suites Stewart Airport 10/10 Excellent "The property is somewhat worn. It needs facelift." [](https://expedia.ca/Newburgh-Hotels-Homewood-Suites-Stewart-Airport.h1764709.Hotel-Information) ![Quality Inn Poughkeepsie](//images.trvl-media.com/lodging/1000000/10000/6500/6465/a647c710_y.jpg) ### Quality Inn Poughkeepsie 10/10 Excellent "Really wonderful staff." [](https://expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Poughkeepsie.h6465.Hotel-Information) ![Inn on the Hudson](//images.trvl-media.com/lodging/2000000/1150000/1148900/1148858/b1419d47_y.jpg) ### Inn on the Hudson 8/10 Good "The view is gorgeous; I was able to check in a little early; it's within walking distance of the train station; and the room was clean overall. The tub was a bit mildewy, but other than that, it was fine for a short stay. Breakfast was only bagged and to go. There was coffee and tea in the lobby morning and evening. " [](https://expedia.ca/White-Plains-Hotels-Inn-On-The-Hudson.h1148858.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. [Quality Inn Poughkeepsie](https://www.expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Poughkeepsie.h6465.Hotel-Information): Hotel, 7-minute walk from Vassar College. Provides daily, an indoor pool, and free self parking. [Wildflower Farms, Auberge Collection](https://www.expedia.ca/Gardiner-Hotels-Wildflower-Farms.h79873064.Hotel-Information): Features a full-service spa, a seasonal outdoor pool, and 3 bars. [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? > Explore places like Woodbury Common Premium Outlets and LEGOLAND® New York while you're in the area. Make a point to visit attractions like Lake Tiorati Beach and Algonquin Park. 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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[Ski Hotels in Central New York City](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Ski-Hotel.0-n553248633938969338-0-tSkiHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Central New York City](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Spa-Hotel.0-n553248633938969338-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Central New York City](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Waterpark-Hotels.0-n553248633938969338-0-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Hotel Wedding Venues Hotels in Central New York City](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Wedding-Hotels.0-n553248633938969338-0-tWeddingHotels.Travel-Guide-Filter-Hotels) - [Winery Hotels in Central New York City](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Winery-Hotel.0-n553248633938969338-0-tWineryHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Cornwall](https://www.expedia.ca/Cornwall-Hotels-Cheap-Hotels.0-0-d6052301-tCheapHotels.Travel-Guide-Filter-Hotels) - 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