Title: Book the Best HISTORIC Hotels in Montgomery in 2026 | Expedia.ca

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![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 $132

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## Check availability on Montgomery Historic Hotels

Tonight

[Dec 15 - Dec 16](https://www.expedia.ca/Hotel-Search?regionId=8728&startDate=2025-12-15&endDate=2025-12-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 16 - Dec 17](https://www.expedia.ca/Hotel-Search?regionId=8728&startDate=2025-12-16&endDate=2025-12-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=8728&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=8728&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for 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

[](https://www.expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information)

Bear Mountain

8.4/10

Very good

(1001)

"Staff was incredibly kind and the room was super cozy. The inn is beautiful and there is enough to do around. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ryan

CA $143

CA $162 total

includes taxes & fees

Jan 15 - Jan 16, 2026

[](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)

![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)

![Reception](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/a90c96fc.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

(1004)

"Clean room and friendly staff "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kelly

CA $125

CA $142 total

includes taxes & fees

Dec 21 - Dec 22

[](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)

![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)

![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)

### Hampton Inn Fishkill

[](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Fishkill.h119273.Hotel-Information)

Fishkill

8.6/10

Excellent

(1004)

"Clean, friendly, nice pool!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kate

CA $117

CA $132 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](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)

![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

[](https://www.expedia.ca/Beacon-Hotels-Luxe-Studio-4-On-Main-Street-Luxury-Steam-Shower.h69240003.Hotel-Information)

Beacon

10/10

Exceptional

(49)

"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 $151

CA $327 total

includes taxes & fees

Dec 16 - Dec 17

[](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)

![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/67801e28.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)

![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

(129)

"It has an incredible mountain and water view. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

MIHYUN

CA $259

CA $422 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.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=2025-12-29&endDate=2025-12-30&regionId=8728&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true)

## Top Montgomery Hotel Reviews

![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

"Love it, everytime we come this is the place to stay"

[](https://expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.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

"😍"

[](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information)

![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

"Staff was incredibly kind and the room was super cozy. The inn is beautiful and there is enough to do around. "

[](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.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)

![Quality Inn Poughkeepsie](https://images.trvl-media.com/lodging/1000000/10000/6500/6465/a647c710_y.jpg)

### Quality Inn Poughkeepsie

10/10 Excellent

"Best stay!"

[](https://expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Poughkeepsie.h6465.Hotel-Information)

## Frequently asked questions

### What should a history enthusiast expect from a trip to Montgomery?

### How many historical hotels are there in Montgomery?

### What are the top historical sites and other places to visit in Montgomery?

### What is a historic hotel like in Montgomery?

### What is the difference between a historic hotel and a heritage hotel?

### Do historic hotels in Montgomery have modern facilities?

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