Title: Book the Best HISTORIC Hotels 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 Historic Hotels 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 Historic Hotels Tonight [Sep 28 - Sep 29](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2025-09-28&endDate=2025-09-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 29 - Sep 30](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2025-09-29&endDate=2025-09-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top New Windsor Historic Hotels ![Standard Room, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/30000/23600/23534/279a3a48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/23600/23534/5e614fd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/1000000/30000/23600/23534/4192dc82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Combined shower/tub, free toiletries, hair dryer, towels](https://images.trvl-media.com/lodging/1000000/30000/23600/23534/922b3941.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Countryside Inn & Suites New Windsor 5.2/10 (165) "Perfect and great cost" [](https://www.expedia.ca/Newburgh-Hotels-Econo-Lodge-Near-Stewart-Inter.h23534.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/1047d873.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) ### Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point New Windsor 8.4/10 Very good (1018) "Great price for a great hotel" CA $137 CA $155 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ![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/2000000/1770000/1764800/1764709/0e18f638.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1770000/1764800/1764709/945aae91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/2000000/1770000/1764800/1764709/d51e63c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites Stewart Airport New Windsor 9.2/10 Wonderful (1003) "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 $253 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Newburgh-Hotels-Homewood-Suites-Stewart-Airport.h1764709.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=2025-10-12&endDate=2025-10-13®ionId=10021&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top New Windsor Hotel Reviews ![Hampton Inn & Suites Poughkeepsie](//images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/47fa2e85_y.jpg) ### Hampton Inn & Suites Poughkeepsie 10/10 Excellent "Nice staff at check in and check out. Room was clean and comfortable. Breakfast was much appreciated. " [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information) ![Quality Inn & Suites Fishkill South near I-84](//images.trvl-media.com/lodging/2000000/1770000/1766700/1766609/12805cb0_y.jpg) ### Quality Inn & Suites Fishkill South near I-84 10/10 Excellent "Convenient, great parking, quiet, comfortable room with a friendly staff." [](https://expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Suites-Fishkill-South-Near-I-84.h1766609.Hotel-Information) ![Overlook Lodge at Bear Mountain](//images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/670b74a6_y.jpg) ### Overlook Lodge at Bear Mountain 10/10 Excellent "Wonderful staff!" [](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.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 "I stay here a lot. Never a bad experience." [](https://expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ![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 "Great! Breakfast and perfect for groups. " [](https://expedia.ca/Poughkeepsie-Hotels-Holiday-Inn-Express-Poughkeepsie.h12157.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 "Everything about our stay was fine except don't be counting on the breakfast. It left a lot to be desired." [](https://expedia.ca/Poughkeepsie-Hotels-Americas-Best-Value-Inn-New-Paltz.h897882.Hotel-Information) ![Quality Inn Poughkeepsie](//images.trvl-media.com/lodging/1000000/10000/6500/6465/a647c710_y.jpg) ### Quality Inn Poughkeepsie 10/10 Excellent "I would have given the property a five if the ac had been working properly. " [](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 hotel was very nice. I would stay there again. Quiet at night. The view of the river is breath taking. I enjoyed morning coffee outside. The grab and go breakfast is convenient, but carb heavy for those who need to watch their sugar intake. The event space would make a great place for a party, but the patio could use some sprucing up. I enjoyed the flannel blanket between two top sheets; warm and cosey for cold nights. Wood floors are a rustic touch. Shower was great; plenty of hot water. " [](https://expedia.ca/White-Plains-Hotels-Inn-On-The-Hudson.h1148858.Hotel-Information) ![The Crossroads Hotel, Newburgh](//images.trvl-media.com/lodging/1000000/20000/14500/14410/5440914b_y.jpg) ### The Crossroads Hotel, Newburgh 10/10 Excellent "The staff was efficient. The rooms were clean the common areas i.e. hallways need to be updated and repaired. The hotel is very quiet. The rooms are nice. I’d stay here again." [](https://expedia.ca/Newburgh-Hotels-The-Crossroads-Hotel.h14410.Hotel-Information) ## Frequently asked questions ### What should a history enthusiast expect from a trip to New Windsor? > You're already probably planning a visit to sights of historical relevance while you're staying in New Windsor. While you're here, you can visit the shops and lakeside. And also relish a stop at the top-notch restaurants in this family-friendly area. ### How many historical hotels will I find in New Windsor? > New Windsor is home to 11 hotels and other lodging options bookable on Expedia though not many historic hotels to choose from. ### What are the must-see historical places and other sights in New Windsor? > Landmarks like New Windsor Cantonment State Historic Site and Knox's Headquarters State Historic Site in New Windsor might be worth a visit. Additionally, in the area you'll find Woodbury Common Premium Outlets and LEGOLAND® New York. ### What is a historic hotel like in New Windsor? > Guests who choose a historic hotel can stay in a place that has an officially recognized historic designation. A palace, castle, grand home or even an old police station, pub, lodge, or skyscraper can be identified as a historic hotel provided that it has special significance. Traditional architecture and period features are often preserved in the guestrooms or communal spaces of these historic hotels in New Windsor, giving a historical feel. ### What is the difference between a historic hotel and a heritage hotel? > "Heritage hotel" is more common in Asia and Europe, while "historic hotel" is a term often used in the U.S. though overall the terms are quite similar. The building and architecture of a historic hotel is generally what's most important. For a heritage hotel, often it's the cultural value as well as how it shaped the community. ### Do historic hotels in New Windsor have modern facilities? > Hotels have the safety features and modern conveniences you might expect, but every effort is made to preserve treasured traditions and historic facades. Smart TVs, WiFi, updated bathroom facilities, and the usual amenities found in any hotel will be available in a historic hotel. 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