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Find Historic Hotels in New Windsor, NY

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Our top choices for New Windsor historic hotels

Restaurant
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1000)
"Staff was incredibly kind and the room was super cozy. The inn is beautiful and there is enough to do around. "
United States
Ryan
The price is AED 389
AED 440 total
includes taxes & fees
17 Dec - 18 Dec
Overlook Lodge at Bear Mountain
Exterior
Courtyard by Marriott Poughkeepsie

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
The price is AED 307
AED 348 total
includes taxes & fees
25 Dec - 26 Dec
Courtyard by Marriott Poughkeepsie
Exterior
Hampton Inn Fishkill

Hampton Inn Fishkill

Hampton Inn Fishkill
2.5 star property
Fishkill
8.6 out of 10, Excellent, (1000)
"Clean, friendly, nice pool!"
United States
Kate
The price is AED 329
AED 372 total
includes taxes & fees
4 Jan - 5 January 2026
Hampton Inn Fishkill
Game room
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food

Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food

Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (90)
"I had a great stay at this extremely comfortable home in a quiet neighborhood. Maria was very welcoming and helpful. I hope to visit and stay here again soon."
United States
Jill D.
The price is AED 360
AED 953 total
includes taxes & fees
11 Dec - 12 Dec
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
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

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.
The price is AED 404
AED 892 total
includes taxes & fees
14 Dec - 15 Dec
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

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
The price is AED 690
AED 1,126 total
includes taxes & fees
11 Dec - 12 Dec
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 New Windsor Hotel Reviews

Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

10/10 Excellent
"The was extremely clean"
Dewayne 1-night trip
Posted 4 days ago
Holiday Inn Express Poughkeepsie by IHG

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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. A couple of additional sights to add to your agenda are National Purple Heart Hall of Honor and Schunnemunk State Park.
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. Rest assured that when you select a historic hotel in New Windsor, you won't be staying at a place that's uncomfortable or rundown.