Title: The Best New Windsor, NY Chalets from $250 | 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_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 [Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=10021&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=10021&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=10021&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 24 - Jul 26](https://www.expedia.com/Hotel-Search?regionId=10021&startDate=2026-07-24&endDate=2026-07-26&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) ![Dining](https://images.trvl-media.com/lodging/108000000/107970000/107964300/107964203/96050ad7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/108000000/107970000/107964300/107964203/e7e8be7c.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) ### 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. $247 nightly $250 total Apr 19 - Apr 20 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=2026-04-17&endDate=2026-04-18®ionId=10021&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## 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=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=CABIN) 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=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=COTTAGE) 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=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=VACATION_HOME) 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=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=VILLA) 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=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=APARTMENT) 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=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=APART_HOTEL) 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=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&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=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&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 ![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 "The staff was very friendly and courteous. The room was Great! They provide "Dove" soaps and lotions. The bathroom floor was super slippery after you shower. The breakfast was nice. There was a nice variety. The juice machine wasnt working during our stay, but they had bottles of yummy chocolate milk. I was hoping for bacon as shown in one of the photos, its my favorite, but there was sausage, which was good too. The pool was nice. The jets in the hot tub were barely working. Overall, I'd deff stay there again." [](https://expedia.com/Poughkeepsie-Hotels-Holiday-Inn-Express-Fishkill-Mid-Hudson-Valley.h1680342.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 "Room was clean and comfortable. The bartender was wonderful and breakfast was delicious." [](https://expedia.com/Hyde-Park-Hotels-Inn-At-Bellefield-Hyde-Park.h99850733.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 "Parking was great. Rooms were clean. " [](https://expedia.com/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ![Hampton Inn Harriman Woodbury](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/e0fcb0f3_y.jpg) ### Hampton Inn Harriman Woodbury 8/10 Good "Staff was awesome! Loved the shuttle to Woodbury Common." [](https://expedia.com/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ![Wildflower Farms, Auberge Collection](https://images.trvl-media.com/lodging/80000000/79880000/79873100/79873064/2028d4aa_y.jpg) ### Wildflower Farms, Auberge Collection 10/10 Excellent "Everything was superb. Beautiful facilities. Impeccable service. Flawless attention to detail. Terrific style. Delicious food. Wonderful activities. Absolutely divine! One of the best vacations I have ever had, and one of the most delightful properties I have ever visited." [](https://expedia.com/Gardiner-Hotels-Wildflower-Farms.h79873064.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 4/10 Poor "Bathroom toilet was not cleaned nor flushed. Someone had used it, not flushed. My 5 year old daughter went in as soon as we walked in the room and told us about it. I was offered to change rooms which meant I would have had to drive another mile back to the main lobby to get new card. I decided to clean the toilet and flush it myself. VERY bad, yet a simple thing that should not occur." [](https://expedia.com/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.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 8/10 Good "Parking was easy, breakfast was fine, room was clean." [](https://expedia.com/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.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 4/10 Poor "The only thing saving the Courtyard Marriot is the front desk staff. The manager Margaret is rude and condescending, will never return to that hotel in Middletown, NY. " [](https://expedia.com/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.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 "Very clean. Nice room. Noce property " [](https://expedia.com/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.Hotel-Information) ## Find out more about New Windsor ## New Windsor Chalets information | Number of reviews | 11 | | ----------------- | --------- | | Accommodation | 3 Chalets | | Lowest Price | $250 | | Highest Price | $250 | ## 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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