Title: Book the Best HISTORIC Hotels in Montgomery in 2025 | Expedia.ca [Hotels in Montgomery](https://expedia.ca/Montgomery-Hotels.d8728.Travel-Guide-Hotels)[Vacation Rentals in Montgomery](https://expedia.ca/Montgomery-Vacation-Rentals.d8728.Travel-Guide-VacationRentals)[Things to do in Montgomery](https://expedia.ca/Things-To-Do-In-Montgomery.d8728.Travel-Guide-Activities)[Montgomery Car Rentals](https://expedia.ca/Car-Rentals-In-Montgomery.d8728.Car-Rental-Guide)[Montgomery Vacation Packages](https://expedia.ca/Montgomery.d8728.Destination-Travel-Guides) ![Autumn foliage in the Mohawk Valley, Montgomery County, New York State, USA.](https://images.trvl-media.com/place/8728/e92a028d-f2c6-4a41-a280-7692010fed7a.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Montgomery, NY from CA $147 - ![](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 Montgomery Historic Hotels Tonight [Nov 30 - Dec 1](https://www.expedia.ca/Hotel-Search?regionId=8728&startDate=2025-11-30&endDate=2025-12-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 1 - Dec 2](https://www.expedia.ca/Hotel-Search?regionId=8728&startDate=2025-12-01&endDate=2025-12-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=8728&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=8728&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Montgomery Historic Hotels ![Restaurant](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/670b74a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed, Non Smoking (Stone Cottages at Bear Mountain)](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/42067525.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) ![Lobby](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/13890846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Overlook Lodge at Bear Mountain Bear Mountain 8.4/10 Very good (1023) "Parking was very easy, beautiful area, very nice staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth CA $143 CA $162 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.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) ![Premium bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/8529e0e4.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) ![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) ### Hampton Inn Fishkill Fishkill 8.6/10 Excellent (1004) "Was a great experience " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) george CA $133 CA $151 total includes taxes & fees Dec 12 - Dec 13 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Fishkill.h119273.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) ![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) ![Living area](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/dc93786c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Poughkeepsie Poughkeepsie 8.8/10 Excellent (1010) "Clean room, staff is friendly especially at the cafe. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cynthia CA $130 CA $147 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.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) ![Interior](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/e56d490f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/67801e28.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 Fort Montgomery 9.8/10 Exceptional (129) "It has an incredible mountain and water view. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MIHYUN CA $263 CA $430 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/ab271dba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/04adf8dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/13b54d67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/97dee96b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer Beacon 10/10 Exceptional (47) "Great room and location. A nice home base for exploring the area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bob G. CA $157 CA $340 total includes taxes & fees Dec 7 - Dec 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=2025-12-14&endDate=2025-12-15®ionId=8728&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AFFINITY_BF_PROMO_8728) ## Top Montgomery Hotel Reviews ![Overlook Lodge at Bear Mountain](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/670b74a6_y.jpg) ### Overlook Lodge at Bear Mountain 10/10 Excellent "Great hotel - beautiful property, comfortable accommodation, fireplace in cottage and scenic views from balcony " [](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![Hampton Inn & Suites Poughkeepsie](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/47fa2e85_y.jpg) ### Hampton Inn & Suites Poughkeepsie 10/10 Excellent "The staff was very nice and accommodating. The room was perfect and the bed was super comfortable. Will stay again if in the area." [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.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 "Staff was great. Rooms were updated. Shower heads were the big rain shower type. The beds were comfortable, not too soft. Breakfast buffet was a notch above others. " [](https://expedia.ca/Poughkeepsie-Hotels-Holiday-Inn-Express-Poughkeepsie.h12157.Hotel-Information) ![SureStay Plus Hotel by Best Western Highland Poughkeepsie](https://images.trvl-media.com/lodging/1000000/920000/918800/918797/960f4844_y.jpg) ### SureStay Plus Hotel by Best Western Highland Poughkeepsie 10/10 Excellent "Nice room, nice staff" [](https://expedia.ca/Poughkeepsie-Hotels-SureStay-Plus-Hotel-By-Best-Western-Highland-Poughkeepsie.h918797.Hotel-Information) ![Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/e8f6eb1b_y.jpg) ### Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point 10/10 Excellent "Very friendly front desk staff!" [](https://expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ![Borland House Inn](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/47637293_y.jpg) ### Borland House Inn 10/10 Excellent "I arrived on a dark and windy night and was immediately welcomed with coziness and warmth. Next time I hope to meet the corgis who are part of the management team. " [](https://expedia.ca/Newburgh-Hotels-Borland-House-Inn.h11796055.Hotel-Information) ## Frequently asked questions ### What should a history enthusiast expect from a trip to Montgomery? > You'll probably want to seek out the places with historical relevance during your trip to Montgomery. Why not absorb the local color with a visit to the restaurants? ### How many historical hotels are there in Montgomery? > Montgomery is home to 23 hotels and other lodging options bookable on Expedia though you won't find many designated historic hotels. ### What are the top historical sites and other places to visit in Montgomery? > Favorite places to visit include City Winery Hudson Valley, Orange County Arboretum, and Highland Lakes State Park. A couple of additional sights to add to your agenda are Orange County Tennis Center and Thomas Bull Memorial Park. ### What is a historic hotel like in Montgomery? > When you choose a historic hotel, you'll stay someplace that has an officially recognized historic designation. A palace, castle, stately home or even a lodge, pub, or skyscraper can be identified as a historic hotel as long as it's of special interest. Traditional architecture and period features are often preserved in the public spaces and guestrooms of historic hotels in Montgomery, giving a real sense of character. ### What is the difference between a historic hotel and a heritage hotel? > "Heritage hotel" is a term often used in Asia and Europe, while "historic hotel" is more common in the U.S. though overall the terms are quite similar. The architecture and actual building of a historic hotel tends to be what's most important. For a heritage hotel, it's often the cultural value as well as how it shaped the community. ### Do historic hotels in Montgomery have modern facilities? > Hotels have the safety features and modern conveniences you expect to find, while every effort is made to preserve historic facades and treasured traditions. Smart TVs, WiFi, updated bathroom facilities, and the usual amenities found in most hotels should be available at a historic hotel. Rest assured that when you select a historic hotel in Montgomery, you won't find yourself staying at a place that is rundown or uncomfortable. ## Explore a world of travel with Expedia - Lodging - More ways to book - [Cheap Hotels in Blooming Grove](https://www.expedia.ca/Blooming-Grove-Hotels-Cheap-Hotels.0-0-d3000448042-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in Blooming Grove](https://www.expedia.ca/Blooming-Grove-Hotels-Hotels-With-Free-Breakfast.0-0-d3000448042-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Campbell Hall](https://www.expedia.ca/Campbell-Hall-Hotels-Cheap-Hotels.0-0-d6338665-tCheapHotels.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Central New York City](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Adults-Only-Resorts.0-n553248633938969338-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Central New York City](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Beach-Hotel.0-n553248633938969338-0-tBeachHotel.Travel-Guide-Filter-Hotels) - 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