Title: The Best New Windsor, NY Chalets from $221 | 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) ![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 ![](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_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=10021&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=10021&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=10021&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 3 - Jul 5](https://www.expedia.com/Hotel-Search?regionId=10021&startDate=2026-07-03&endDate=2026-07-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for New Windsor chalets ![Exterior](https://images.trvl-media.com/lodging/108000000/107970000/107964300/107964203/75814d07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107970000/107964300/107964203/bf85ab49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107970000/107964300/107964203/9714c3f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/108000000/107970000/107964300/107964203/96050ad7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna [](https://www.expedia.com/Gardiner-Hotels-Modern-Zen-Chalet-At-The-Foot-Of-Gunks-W-Mt-View.h107964203.Hotel-Information) Gardiner 10/10 Exceptional (11 reviews) "Great weekend getaway to reconnect with old friends!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa D. $219 nightly $221 total Mar 18 - Mar 19 Total with taxes and fees [](https://www.expedia.com/Gardiner-Hotels-Modern-Zen-Chalet-At-The-Foot-Of-Gunks-W-Mt-View.h107964203.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=2026-03-26&endDate=2026-03-27®ionId=10021&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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.com/deals?rfrr=AA_SPRING_PROMO_10021) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/Hotel-Search?destination=New+Windsor%2C+New+York%2C+United+States+of+America®ionId=10021&latLong=41.476761%2C-74.02375&adults=2&startDate=2026-06-10&d1=2026-06-10&endDate=2026-06-13&d2=2026-06-13&lodging=CABIN) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=New+Windsor%2C+New+York%2C+United+States+of+America®ionId=10021&latLong=41.476761%2C-74.02375&adults=2&startDate=2026-06-10&d1=2026-06-10&endDate=2026-06-13&d2=2026-06-13&lodging=VACATION_HOME) Cottages [](https://www.expedia.com/Hotel-Search?destination=New+Windsor%2C+New+York%2C+United+States+of+America®ionId=10021&latLong=41.476761%2C-74.02375&adults=2&startDate=2026-06-10&d1=2026-06-10&endDate=2026-06-13&d2=2026-06-13&lodging=COTTAGE) Villas [](https://www.expedia.com/Hotel-Search?destination=New+Windsor%2C+New+York%2C+United+States+of+America®ionId=10021&latLong=41.476761%2C-74.02375&adults=2&startDate=2026-06-10&d1=2026-06-10&endDate=2026-06-13&d2=2026-06-13&lodging=VILLA) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=New+Windsor%2C+New+York%2C+United+States+of+America®ionId=10021&latLong=41.476761%2C-74.02375&adults=2&startDate=2026-06-10&d1=2026-06-10&endDate=2026-06-13&d2=2026-06-13&lodging=APART_HOTEL) Apartments [](https://www.expedia.com/Hotel-Search?destination=New+Windsor%2C+New+York%2C+United+States+of+America®ionId=10021&latLong=41.476761%2C-74.02375&adults=2&startDate=2026-06-10&d1=2026-06-10&endDate=2026-06-13&d2=2026-06-13&lodging=APARTMENT) Condos [](https://www.expedia.com/Hotel-Search?destination=New+Windsor%2C+New+York%2C+United+States+of+America®ionId=10021&latLong=41.476761%2C-74.02375&adults=2&startDate=2026-06-10&d1=2026-06-10&endDate=2026-06-13&d2=2026-06-13&lodging=CONDO) Chalets [](https://www.expedia.com/Hotel-Search?destination=New+Windsor%2C+New+York%2C+United+States+of+America®ionId=10021&latLong=41.476761%2C-74.02375&adults=2&startDate=2026-06-10&d1=2026-06-10&endDate=2026-06-13&d2=2026-06-13&lodging=CHALET) ![](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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FNew-Windsor-Chalets.d10021-aaChalets.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FNew-Windsor-Chalets.d10021-aaChalets.Travel-Guide-Accommodation) ## Top New Windsor Hotel Reviews ![Courtyard by Marriott Fishkill](https://images.trvl-media.com/lodging/1000000/20000/17300/17286/3f9cb655_y.jpg) ### Courtyard by Marriott Fishkill 10/10 Excellent "Easy parking and the staff was amazing. Rooms are-dead quiet! Never slept so well in a hotel. Beautiful rooms and clean!! " [](https://expedia.com/Poughkeepsie-Hotels-Courtyard-By-Marriott-Fishkill.h17286.Hotel-Information) ![Holiday Inn Express Fishkill-Mid Hudson Valley by IHG](https://images.trvl-media.com/lodging/2000000/1690000/1680400/1680342/5b94363e_y.jpg) ### Holiday Inn Express Fishkill-Mid Hudson Valley by IHG 10/10 Excellent "Staff was great, breakfast was great, best ever " [](https://expedia.com/Poughkeepsie-Hotels-Holiday-Inn-Express-Fishkill-Mid-Hudson-Valley.h1680342.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 "Jenis was a great help " [](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 "Very nice" [](https://expedia.com/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/aeade474_y.jpg) ### Sleep Inn & Suites Middletown - Goshen 10/10 Excellent "Excellent beds, room, swimming pool, and breakfast. Well worth paying more in comparison to other places." [](https://expedia.com/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information) ![Hampton Inn Harriman Woodbury](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/e0fcb0f3_y.jpg) ### Hampton Inn Harriman Woodbury 10/10 Excellent "Great plave" [](https://expedia.com/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.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 "Great stay!!! " [](https://expedia.com/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.Hotel-Information) ![Hampton Inn & Suites Poughkeepsie](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/ee108dad_y.jpg) ### Hampton Inn & Suites Poughkeepsie 6/10 Okay "We found a bug in our bed. Using Google image it was identified as a bed bug. We went to the front desk and they relocated us to a different floor and upgraded us to a suite. It left us uneasy but we were happy the staff took us seriously. " [](https://expedia.com/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information) ![Inn at Bellefield / Hyde Park, Residence Inn by Marriott](https://images.trvl-media.com/lodging/100000000/99860000/99850800/99850733/1ee75d40_y.jpg) ### Inn at Bellefield / Hyde Park, Residence Inn by Marriott 10/10 Excellent "This is one of the best hotel stays my wife and I have had ever. " [](https://expedia.com/Hyde-Park-Hotels-Inn-At-Bellefield-Hyde-Park.h99850733.Hotel-Information) ## Find out more about New Windsor ## New Windsor Chalets information | Number of reviews | 11 | | ----------------- | --------- | | Accommodation | 3 Chalets | | Lowest Price | $221 | | Highest Price | $221 | ## 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) - [Newburgh Hotels ](https://www.expedia.com/Newburgh-Hotels.d6023343.Travel-Guide-Hotels) - [Motels in Newburgh ](https://www.expedia.com/Newburgh-Motels.d6023343-aaMotels.Travel-Guide-Accommodation) - [Hotels near Delano-Hitch Recreation Park ](https://www.expedia.com/Delano-Hitch-Recreation-Park-Hotels.0-l6182277-0.Travel-Guide-Filter-Hotels) - 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