Title: Book the Best New Windsor WINERY Hotels in 2026 | 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 Winery Hotels in New Windsor, NY from CA $137 - ![](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 Winery Hotels Tonight [Dec 10 - Dec 11](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2025-12-10&endDate=2025-12-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 11 - Dec 12](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2025-12-11&endDate=2025-12-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for New Windsor hotels with winery ![Indoor pool](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/bd59d6cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/dab27d3b.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) ### Hampton Inn by Hilton New Paltz [](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.Hotel-Information) New Paltz 9.4/10 Exceptional (1000) "The hotel is quiet and clean and had a very comfortable bed." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carolyn CA $154 CA $172 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/98944f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/fe354234.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/f3b7bb7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/dc5981dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Montgomery by IHG [](https://www.expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Suites-Montgomery.h7814618.Hotel-Information) Montgomery 8.8/10 Excellent (795) "Good stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Fatima CA $125 CA $141 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Suites-Montgomery.h7814618.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/990080f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/2b66e26d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/a90c96fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/1765b81e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Poughkeepsie [](https://www.expedia.ca/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.Hotel-Information) Poughkeepsie 8.8/10 Excellent (1003) "Clean room and friendly staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelly CA $121 CA $137 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/e1e7e350.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/2831de3d.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) ![Sports facility](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/2f2f704a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Fishkill [](https://www.expedia.ca/Poughkeepsie-Hotels-Hilton-Garden-Inn-Fishkill.h890436.Hotel-Information) Fishkill 8.6/10 Excellent (1006) "Brayden was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Will CA $126 CA $143 total includes taxes & fees Dec 25 - Dec 26 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hilton-Garden-Inn-Fishkill.h890436.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/220000/216900/216870/d6a17faf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/220000/216900/216870/bc5eecd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/220000/216900/216870/75a6f271.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/220000/216900/216870/afb43ef1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus The Inn & Suites At The Falls [](https://www.expedia.ca/Poughkeepsie-Hotels-Best-Western-Plus-The-Inn-Suites-At-The-Falls.h216870.Hotel-Information) Red Oaks Mill 7.6/10 Good (436) "Nice and quaint hotel with beautiful creek behind surrounded by a dorest" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hiram CA $144 CA $163 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Poughkeepsie-Hotels-Best-Western-Plus-The-Inn-Suites-At-The-Falls.h216870.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/7472348e.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) ![Restaurant](https://images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/1732edca.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) ### Home2 Suites By Hilton Poughkeepsie [](https://www.expedia.ca/Poughkeepsie-Hotels-Home2-Suites-By-Hilton-Poughkeepsie.h103394153.Hotel-Information) Poughkeepsie 9.4/10 Exceptional (390) "Beautiful room and great staff! Would stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christina CA $150 CA $174 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Poughkeepsie-Hotels-Home2-Suites-By-Hilton-Poughkeepsie.h103394153.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/47637293.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/49ef52ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hanlon Suite | Children's theme room](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/05c3d7b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/25051ab3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borland House Inn [](https://www.expedia.ca/Newburgh-Hotels-Borland-House-Inn.h11796055.Hotel-Information) Montgomery 9.2/10 Wonderful (144) "Had a great stay at the the Borland House Inn a historical setting in a cute town with wonderful staff and a delicious breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah [](https://www.expedia.ca/Newburgh-Hotels-Borland-House-Inn.h11796055.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/7494afa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/b3546f42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, open 6 AM to 11 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/9b9c3b93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/2a01f3da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Newburgh Stewart Airport [](https://www.expedia.ca/Newburgh-Hotels-Courtyard-By-Marriott-Newburgh-Stewart-Airport.h42673.Hotel-Information) Newburgh 8.2/10 Very good (694) "Property clean rooms clean front desk the Best " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dirwin CA $139 CA $165 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Newburgh-Hotels-Courtyard-By-Marriott-Newburgh-Stewart-Airport.h42673.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/f57ee72e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/w3831h2553x9y7-9c25ee45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/0c0edcb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/f3387c76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Fishkill [](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Fishkill.h119273.Hotel-Information) Fishkill 8.6/10 Excellent (1000) "Clean, friendly, nice pool!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kate CA $124 CA $140 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Fishkill.h119273.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1210000/1201800/1201707/3be04d40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/2000000/1210000/1201800/1201707/36df0c61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining room](https://images.trvl-media.com/lodging/2000000/1210000/1201800/1201707/5166d865.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1210000/1201800/1201707/f43255d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Minnewaska Lodge [](https://www.expedia.ca/Poughkeepsie-Hotels-Minnewaska-Lodge.h1201707.Hotel-Information) Gardiner 9.0/10 Wonderful (524) "Great peaceful stay. Can’t wait to go back :)" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Makeda CA $173 CA $213 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Poughkeepsie-Hotels-Minnewaska-Lodge.h1201707.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=2025-12-25&endDate=2025-12-26®ionId=10021&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top New Windsor Hotel Reviews ![Hampton Inn & Suites Poughkeepsie](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/47fa2e85_y.jpg) ### Hampton Inn & Suites Poughkeepsie 10/10 Excellent "😍" [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.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 "He was excellent our two nights and thank again, see you soon." [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ![Holiday Inn Express Poughkeepsie by IHG](https://images.trvl-media.com/lodging/1000000/20000/12200/12157/9d729415_y.jpg) ### Holiday Inn Express Poughkeepsie by IHG 10/10 Excellent "The was extremely clean" [](https://expedia.ca/Poughkeepsie-Hotels-Holiday-Inn-Express-Poughkeepsie.h12157.Hotel-Information) ![Homewood Suites Stewart Airport](https://images.trvl-media.com/lodging/2000000/1770000/1764800/1764709/771d3275_y.jpg) ### Homewood Suites Stewart Airport 10/10 Excellent "Great place. Service was good. Place spotless and welcoming. 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