Title: Book the Best HISTORIC Hotels in New Windsor 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 ![](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__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 Historic Hotels Tonight [Mar 17 - Mar 18](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2026-03-17&endDate=2026-03-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 18 - Mar 19](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2026-03-18&endDate=2026-03-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2026-03-20&endDate=2026-03-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2026-03-27&endDate=2026-03-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for New Windsor historic hotels ![Reception](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/679bdd4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/7384700a.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) ![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) ### Overlook Lodge at Bear Mountain [](https://www.expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) Bear Mountain 8.4/10 Very good (1,006 reviews) "Great staff and clean rooms. Beautiful views." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Renee CA $132 CA $150 total includes taxes & fees Mar 18 - Mar 19 [](https://www.expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/3a9ea66f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/c55e3667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/dfec5e09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/5ed95c10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands [](https://www.expedia.ca/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.Hotel-Information) Fort Montgomery 9.8/10 Exceptional (132 reviews) "Amazing place Thanks for the stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julien C. CA $257 CA $420 total includes taxes & fees Mar 18 - Mar 19 [](https://www.expedia.ca/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/34000000/33260000/33256300/33256205/26fb7343.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33260000/33256300/33256205/4ce09deb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, DVD player, books](https://images.trvl-media.com/lodging/34000000/33260000/33256300/33256205/065339c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33260000/33256300/33256205/422d3d38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food [](https://www.expedia.ca/Croton-On-Hudson-Hotels-Comfortable-2bd-Convenience-Style-45min-To-NYC-Great-Food.h33256205.Hotel-Information) CROTON HDSN 9.8/10 Exceptional (90 reviews) "I had a great stay at this extremely comfortable home in a quiet neighborhood. Maria was very welcoming and helpful. I hope to visit and stay here again soon." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jill D. [](https://www.expedia.ca/Croton-On-Hudson-Hotels-Comfortable-2bd-Convenience-Style-45min-To-NYC-Great-Food.h33256205.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/04adf8dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/a8c5ab99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/c6f43c54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/19de180c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer [](https://www.expedia.ca/Beacon-Hotels-Luxe-Studio-4-On-Main-Street-Luxury-Steam-Shower.h69240003.Hotel-Information) Beacon 10/10 Exceptional (54 reviews) "We havld a good time. The room was comfortable and perfectly located!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandy C. CA $157 CA $342 total includes taxes & fees Apr 7 - Apr 8 [](https://www.expedia.ca/Beacon-Hotels-Luxe-Studio-4-On-Main-Street-Luxury-Steam-Shower.h69240003.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=2026-03-31&endDate=2026-04-01®ionId=10021&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top New Windsor Hotel Reviews ![Hampton Inn & Suites Poughkeepsie](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/ee108dad_y.jpg) ### Hampton Inn & Suites Poughkeepsie 8/10 Good "It was a nice stay, no complaints. We will definitely stay here again next time we are in the area!" [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.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 10/10 Excellent "The place is clean every time I come and outstanding customer service" [](https://expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ![DoubleTree by Hilton Poughkeepsie Convention Center](https://images.trvl-media.com/lodging/1000000/20000/14600/14563/875b6b8c_y.jpg) ### DoubleTree by Hilton Poughkeepsie Convention Center 10/10 Excellent "Very helpful staff and great location, spacious rooms, good views. The parking garage can be a challenge on event days. Breakfast is ok, maybe add more plant based options?" [](https://expedia.ca/Poughkeepsie-Hotels-Poughkeepsie-Grand-Hotel.h14563.Hotel-Information) ![Courtyard by Marriott Poughkeepsie](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/990080f2_y.jpg) ### Courtyard by Marriott Poughkeepsie 6/10 Okay "gym fair. dumbells and some weighted balls. aerobic machines ok(1 needs repair) Why $10\. parking? Fireplace in public area not controlled by front desk? will explore other hotel options next time." [](https://expedia.ca/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.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 10/10 Excellent "We stayed at the cottages which were clean and welcoming. The only thing to keep in mind is that the common area IS common, so if you don’t want to socialize, it might not be the space for you. We had a party with us that all knew each other (and we were the only room who didn’t) and they hung out there all night talking. Not a fault of the property, but maybe stay in the main inn if you’re looking for a little more privacy." [](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.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 "really nice place to stay" [](https://expedia.ca/Poughkeepsie-Hotels-Holiday-Inn-Express-Fishkill-Mid-Hudson-Valley.h1680342.Hotel-Information) ![Spark by Hilton Fishkill](https://images.trvl-media.com/lodging/1000000/10000/2700/2642/b112328f_y.jpg) ### Spark by Hilton Fishkill 6/10 Okay "Did not see many of the things in the hotels description. We had no microwave in the room. Didn't find the work-out room, or laundry. The continental breakfast was very plain, nothing extra. And no restaurant. " [](https://expedia.ca/Fishkill-Hotels-Spark-By-Hilton-Fishkill.h2642.Hotel-Information) ![HYATT house Fishkill/Poughkeepsie](https://images.trvl-media.com/lodging/2000000/1340000/1336000/1335929/w3836h2558x4y3-858cbdd6_y.jpg) ### HYATT house Fishkill/Poughkeepsie 6/10 Okay "Appears most staff new and unclear on policies. Very friendly but needs more training " [](https://expedia.ca/Poughkeepsie-Hotels-HYATT-House-FishkillPoughkeepsie.h1335929.Hotel-Information) ![Courtyard by Marriott Fishkill](https://images.trvl-media.com/lodging/1000000/20000/17300/17286/3f9cb655_y.jpg) ### Courtyard by Marriott Fishkill 10/10 Excellent "Very clean and quiet" [](https://expedia.ca/Poughkeepsie-Hotels-Courtyard-By-Marriott-Fishkill.h17286.Hotel-Information) ## Frequently asked questions ### What should a history enthusiast expect from a trip to New Windsor? ### How many historical hotels will I find in New Windsor? ### What are the must-see historical places and other sights in New Windsor? ### What is a historic hotel like in New Windsor? ### What is the difference between a historic hotel and a heritage hotel? ### Do historic hotels in New Windsor have modern facilities? ## Explore a world of travel with Expedia - Lodging - More ways to book - [Boutique Hotels in Beacon ](https://www.expedia.ca/Beacon-Hotels-Boutique-Hotel.0-0-d6173904-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - 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