Find Historic Hotels in Montgomery, NY

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Check availability on Montgomery Historic Hotels

Our top choices for Montgomery historic hotels

Restaurant
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1005)
"Staff was incredibly kind and the room was super cozy. The inn is beautiful and there is enough to do around. "
United States
Ryan
$102 nightly
The price is $116
Dec 10 - Dec 11
Total with taxes and fees
Overlook Lodge at Bear Mountain
Exterior
Courtyard by Marriott Poughkeepsie

Courtyard by Marriott Poughkeepsie

3.0 star property
Poughkeepsie
8.8 out of 10, Excellent, (1002)
"Clean room and friendly staff "
United States
Kelly
$84 nightly
The price is $95
Dec 24 - Dec 25
Total with taxes and fees
Courtyard by Marriott Poughkeepsie
Exterior
Hampton Inn Fishkill

Hampton Inn Fishkill

2.5 star property
Fishkill
8.6 out of 10, Excellent, (1001)
"The room was spotless & the staff was amazing "
United States
Kim
$90 nightly
The price is $101
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hampton Inn Fishkill
Fridge, microwave, oven, stovetop
Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer

Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer

Beacon
10.0 out of 10, Exceptional, (49)
"Great room and location. A nice home base for exploring the area. "
United States
Bob G.
$211 nightly
The price is $243
Dec 14 - Dec 15
Total with taxes and fees
Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery
9.8 out of 10, Exceptional, (129)
"It has an incredible mountain and water view. "
United States
MIHYUN
$272 nightly
The price is $308
Dec 10 - Dec 11
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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.
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Top Montgomery Hotel Reviews

Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

10/10 Excellent
"Clean, people very nice, thank you."
Aaron 2-night trip
Posted 3 days ago
Hampton Inn & Suites Poughkeepsie

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.

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