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) ![](https://mediaim.expedia.com/destination/2/7258650cf3c9c107b2e4d18aa267cfe2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by ViajandoconAna Rustrian # Find Historic Hotels in Montgomery, NY from CA $165 ![](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 [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=8728&startDate=2025-10-13&endDate=2025-10-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=8728&startDate=2025-10-14&endDate=2025-10-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=8728&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=8728&startDate=2025-10-24&endDate=2025-10-26&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) ![Reception](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/679bdd4c.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 (1012) "Clean room, easy parking" CA $145 CA $165 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.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) ![Living area](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/dc93786c.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) ![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) ### Courtyard by Marriott Poughkeepsie Poughkeepsie 8.8/10 Excellent (1009) "Clean room, staff is friendly especially at the cafe. " CA $154 CA $174 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.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) ![Reception](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/f3387c76.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) ![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) ### Hampton Inn Fishkill Fishkill 8.6/10 Excellent (1002) "Nice place" CA $176 CA $200 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Fishkill.h119273.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) ![Interior](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/c6f43c54.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) ![Exterior detail](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/04adf8dc.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 (44) "We had a lovely stay in Beacon. The studio was in a great location with easy access to restaurants. Everything was comfortable. Would definitely recommend this place!" CA $154 CA $340 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Beacon-Hotels-Luxe-Studio-4-On-Main-Street-Luxury-Steam-Shower.h69240003.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) ![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) ![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 (122) "It has an incredible mountain and water view. " CA $263 CA $431 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/39000000/38120000/38112400/38112328/26644f44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/39000000/38120000/38112400/38112328/3f1446d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/39000000/38120000/38112400/38112328/58f902a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/39000000/38120000/38112400/38112328/7319149b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riverfront stone cottage Private dock & boats Personal spa private resort Gardiner 9.8/10 Exceptional (54) "The property is nice and equipped with everything you may need. " CA $567 CA $1,031 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Gardiner-Hotels-Riverfront-Stone-CottagePrivate-Dock-BoatsPersonal-Spaprivate-Resort.h38112328.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=2025-10-27&endDate=2025-10-28®ionId=8728&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Montgomery Hotel Reviews ![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 "Parking area was save" [](https://expedia.ca/Poughkeepsie-Hotels-Americas-Best-Value-Inn-New-Paltz.h897882.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 "Spacious Bathroom " [](https://expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Suites-Fishkill-South-Near-I-84.h1766609.Hotel-Information) ![Hampton Inn & Suites Poughkeepsie](//images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/47fa2e85_y.jpg) ### Hampton Inn & Suites Poughkeepsie 10/10 Excellent "The room was very large and the price was great." [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information) ![Days Inn by Wyndham Wurtsboro](//images.trvl-media.com/lodging/1000000/40000/34300/34237/3073e3e0_y.jpg) ### Days Inn by Wyndham Wurtsboro 10/10 Excellent "Clean room" [](https://expedia.ca/Monticello-Hotels-Days-Inn-By-Wyndham-Wurtsboro.h34237.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 "Incredibly peaceful when walking in the forest. Swimming in the lake and stream was amazing " [](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![DoubleTree by Hilton Poughkeepsie Convention Center](//images.trvl-media.com/lodging/1000000/20000/14600/14563/acc87956_y.jpg) ### DoubleTree by Hilton Poughkeepsie Convention Center 10/10 Excellent "Lovely clean spacious room with beautiful view of the Hudson River and its bridges. Friendly welcoming staff." [](https://expedia.ca/Poughkeepsie-Hotels-Poughkeepsie-Grand-Hotel.h14563.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 "Room was very clean but a little worn. Bed and linens were comfortable. Bathroom was clean. Very quiet. Staff were very welcoming, polite and accommodating. " [](https://expedia.ca/Newburgh-Hotels-The-Crossroads-Hotel.h14410.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 "T" [](https://expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.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 22 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 Orange County Arboretum, City Winery Hudson Valley, and Highland Lakes State Park. Additionally, in the area you'll find LEGOLAND® New York and Woodbury Common Premium Outlets. ### 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. 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