The Best Historic Hotels in New Windsor, NY from AED 454 in 2026

A large suspension bridge at night with illuminated cables and a central tower.

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Our top choices for New Windsor historic hotels

1. Overlook Lodge at Bear Mountain

Bear Mountain

randall

AED 369

AED 454 total

includes taxes & fees

14 Oct - 15 Oct

2. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery

Jasmine

AED 727

AED 1,215 total

includes taxes & fees

14 Sep - 15 Sep

3. Storm King Lodge - Storm King Art Center, West Point, Woodbury Commons Outlets

Mountainville

Robert D.

AED 4,224

AED 5,792 total

includes taxes & fees

14 Sep - 15 Sep

Smart TV, video games, DVD player, books

2 bedrooms, in-room safe, desk, iron/ironing board

4. Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

CROTON HDSN

Aimee S.

Smart TV, fireplace, foosball, table tennis

5. Riverfront stone cottage Private dock & boats Personal spa private resort

Gardiner

Paul T.

AED 1,653

AED 2,937 total

includes taxes & fees

28 Sep - 29 Sep

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Top New Windsor Hotel Reviews

SureStay Plus Hotel by Best Western Highland Poughkeepsie

8/10 Good

"Fairly new, fairly clean Convenient location."

Overlook Lodge at Bear Mountain

8/10 Good

"This location and its history made this Inn a great stopover night for us as we travelled down the East Coast. The scenery is beautiful and the staff are helpful and friendly. This would would be a great place to meet with family members and/or friends to enjoy sharing a cottage (with 6 rooms and a common area) to enjoy a few nights or week together. There is a lot to do in the area and the porch of the cottage lends itself to just sitting and admiring the natural surroundings, especially the lake!"

Holiday Inn Express Poughkeepsie by IHG

8/10 Good

"Parking was super easy with plenty of spaces available at the entrances. The room was clean and relatively quiet. Because the hotel is off the highway there wasn't a lot of road noise. The hallways show a lot of wear and tear but if you get past this aspect and into your room all is acceptable."

Homewood Suites Stewart Airport

10/10 Excellent

"Very good front desk help. Very friendly, the room was extremely clean."

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

10/10 Excellent

"This Red Roof Inn is very clean and the staff is friendly. Minor complain is that the floors feels like there is a film on it that feels a bit slippery, probably from build up of cleaning agent, but room is clean. I enjoyed my stay."

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 14 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. Additionally, you'll find Woodbury Common Premium Outlets in the area.

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.

Find Historic Hotels in New Windsor, NY

Change your mind

Treat yourself

Be picky

Check availability on New Windsor Historic Hotels

Our top choices for New Windsor historic hotels

1. Overlook Lodge at Bear Mountain

2. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

3. Storm King Lodge - Storm King Art Center, West Point, Woodbury Commons Outlets

4. Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

5. Riverfront stone cottage Private dock & boats Personal spa private resort

Top New Windsor Hotel Reviews

SureStay Plus Hotel by Best Western Highland Poughkeepsie

Overlook Lodge at Bear Mountain

Holiday Inn Express Poughkeepsie by IHG

Homewood Suites Stewart Airport

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Frequently asked questions