New Windsor, NY

Travel Guide

A large suspension bridge at night with illuminated cables and a central tower.
A calm lake with rocky shores and green hills in the background.
A rural landscape with autumn-colored trees, rolling hills, and a windmill in the foreground.
A pathway flanked by trees with autumn foliage, leading through a grassy field towards a hill.
A field with tall grasses and leafless trees under a cloudy sky.
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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

2 out of 5
915 Union Ave New Windsor NY
$99 nightly
The price is $117 total per night from Sep 27 to Sep 28
$117 total
Sep 27 - Sep 28
Total with taxes and fees
Book a stay at this business-friendly hotel in New Windsor. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the ...
8.4/10 Very Good! (1,000 reviews)
"The exterior of the Hotel looks very good. It’s the room I didn’t care for. The front desk person was NOT friendly or welcoming. He was sitting and I had to ask him if he could please check me in. The process took way longer than it should. I travel solo and I am always checking the sheets to make ..."

Reviewed on Sep 18, 2026

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

Homewood Suites Stewart Airport

3 out of 5
180 Breunig Rd New Windsor NY
$216 nightly
The price is $256 total per night from Oct 4 to Oct 5
$256 total
Oct 4 - Oct 5
Total with taxes and fees
Stay at this hotel in New Windsor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.2/10 Wonderful! (1,001 reviews)
"This was one of the best hotels we stayed in. It was super clean and family friendly"

Reviewed on Sep 19, 2026

Homewood Suites Stewart Airport
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive Bear Mountain NY
$111 nightly
The price is $137 total per night from Oct 21 to Oct 22
$137 total
Oct 21 - Oct 22
Total with taxes and fees
Book a stay at this spa hotel in Bear Mountain. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
Overlook Lodge at Bear Mountain
See all 1,060 properties in New Windsor
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.
5 bdrm Victorian, built in 1881-With 21 rooms, on a hill on 4 VERY private acres

5 bdrm Victorian, built in 1881-With 21 rooms, on a hill on 4 VERY private acres

New Windsor NY
Stay at this vacation home in New Windsor. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Motorcyclepedia Museum and Newburgh Armory Unity ...
9.8/10 Exceptional! (8 reviews)
"Thank you for sharing this very beautiful home. We were very comfortable and the location was great. We also appreciated the snacks, wine, and stock you had in place when we arrived! Great host!"

Reviewed on Aug 18, 2026

5 bdrm Victorian, built in 1881-With 21 rooms, on a hill on 4 VERY private acres
1 Queen Bed | Non-Smoking, Kitchen

1 Queen Bed | Non-Smoking, Kitchen

Fishkill NY
Stay at this apartment in Fishkill. Enjoy free WiFi, cable/satellite TV service, and air conditioning. Popular attractions Van Wyck Homestead Museum and Fishkill ...
8.8/10 Excellent! (20 reviews)
Do not stay here. It’s a motel 6 that is very dirty. It was so bad I had to bo ...
"Do not stay here. It’s a motel 6 that is very dirty. It was so bad I had to book at another location so do not believe any of the positive reviews. To make it worse the hotel was overbooked. Very misleading listing. Horrible place and not safe."

Reviewed on Sep 12, 2026

1 Queen Bed | Non-Smoking, Kitchen
TRANQUIL MOUNTAIN SOLITUDE

TRANQUIL MOUNTAIN SOLITUDE

Pine Bush NY
Enjoy free WiFi, breakfast (surcharge), and a garden. Popular attractions Ellenville Fault Ice Caves and VerKeerderkill Falls are located nearby.
10/10 Exceptional! (20 reviews)
"Adorable RV in the woods and was a fun experience. This little trailer has everything you need! Everything was thoughtfully put together."

Reviewed on Sep 19, 2026

TRANQUIL MOUNTAIN SOLITUDE
See all properties in New Windsor
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.

Stay near popular New Windsor attractions

New Windsor Cantonment State Historic Site

8.2/10 (12 reviews)
You can find out about the history of New Windsor with a stop at New Windsor Cantonment State Historic Site. You can attend a sporting event while in the area.
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Cities near New Windsor

A waterfront with a covered boat dock, a large red building, and a smaller building in the background.

Newburgh

A train crossing a steel bridge over a valley with autumn-colored trees.

Cornwall

A residential area surrounded by autumn-colored trees and rolling hills.

Cornwall-on-Hudson

A calm lake at sunset with trees and grass along the shore.

Highland Mills

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