Holiday Homes in New Windsor

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Find holiday rentals that suit your style

cabin image
Cabins
Cabins
Apartment image
Apartments
Apartments

Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for New Windsor holiday homes

A modern living room with a sofa, armchairs, a coffee table, and a large window with curtains.

1. NEW! Cozy 3BR Home Near West Point & Hudson Valley - King Bed

NEW! Cozy 3BR Home Near West Point & Hudson Valley - King Bed
New Windsor
The price is NZ$886
includes taxes & fees
13 Dec - 14 Dec
NEW! Cozy 3BR Home Near West Point & Hudson Valley - King Bed
A room with a bay window overlooking a lake and mountains, two green armchairs, a small table with a book and a cup, and a potted plant.

2. Hudson View Hot Tub · Walk to Waterfront

Hudson View Hot Tub · Walk to Waterfront
Newburgh
10.0 out of 10, Exceptional, (1 review)
"The home has recently been renovated and it is very well presented with luxury furnishings and an excellently stocked kitchen. Views are amazing over the Hudson towards Beacon."
United States
Rachel M.
The price is NZ$1,372
includes taxes & fees
17 Nov - 18 Nov
Hudson View Hot Tub · Walk to Waterfront
A modern kitchen with white cabinets, a central island with stools, a stainless steel refrigerator, and a staircase leading to another level.

3. Bright Cornwall-On-Hudson Vacation Rental!

Bright Cornwall-On-Hudson Vacation Rental!
Cornwall-On-Hudson
10.0 out of 10, Exceptional, (35 reviews)
"Very comfortable house and great location."
United States
Betty B.
Bright Cornwall-On-Hudson Vacation Rental!
A deck with wicker furniture and a view of a lake and mountains.

4. House + Suite for 6 · Hot Tub · Walk to River

House + Suite for 6 · Hot Tub · Walk to River
Newburgh
10.0 out of 10, Exceptional, (1 review)
The price is NZ$2,123
includes taxes & fees
15 Nov - 16 Nov
House + Suite for 6 · Hot Tub · Walk to River
A staircase with red carpeted steps, wooden handrails, and string lights.

5. Large,Cozy,Bright Apartment, Business Themed.

Large,Cozy,Bright Apartment, Business Themed.
Newburgh
9.0 out of 10, Wonderful, (17 reviews)
"Very cozy stay with responsive host"
United States
Adhith P.
The price is NZ$1,036
includes taxes & fees
7 Dec - 8 Dec
Large,Cozy,Bright Apartment, Business Themed.
A deck with Adirondack chairs, a fire pit, and a grill.

6. 3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
Cornwall
10.0 out of 10, Exceptional, (16 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is NZ$750
includes taxes & fees
16 Nov - 17 Nov
3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
A blue house with a white porch, a welcome sign, and a mailbox.

7. 3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.4 out of 10, Very good, (7 reviews)
"Space was excellent, the multiple bedrooms with the extra bathroom was great. Kitchen was stocked with utensils, bathrooms were clean, living space was comfortable and cozy."
United States
Christine T.
3BR West Point Retreat-3min to Back Gate+ King Bed
An outdoor patio area with a covered seating area, a pool, and potted plants.

8. Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.2 out of 10, Wonderful, (81 reviews)
"The property was as advertised and met our needs for our trip."
United States
Sara
The price is NZ$583
includes taxes & fees
15 Nov - 16 Nov
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

9. A Cozy Private Suite in a Country Home near New Paltz

A Cozy Private Suite in a Country Home near New Paltz
Wallkill
9.2 out of 10, Wonderful, (20 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
The price is NZ$240
includes taxes & fees
16 Nov - 17 Nov
A Cozy Private Suite in a Country Home near New Paltz
A room with a wooden floor, a white door with a number, and a window with blinds.

10. Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
The price is NZ$644
includes taxes & fees
17 Nov - 18 Nov
Lovely 3BR Home with parking-Walk to WP Gate!
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

11. Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (12 reviews)
"House was exactly as described. Would stay again."
United States
Beth M.
The price is NZ$640
includes taxes & fees
17 Nov - 18 Nov
Fabulous 3bdrm Home w/parking!
A living room with a wooden floor, a black sofa, a coffee table, and a ceiling fan.

12. Perfect 2BR with Free Parking! Walk to West Point!

Perfect 2BR with Free Parking! Walk to West Point!
Highland Falls
The price is NZ$579
includes taxes & fees
16 Nov - 17 Nov
Perfect 2BR with Free Parking! Walk to West Point!
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

13. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.4 out of 10, Exceptional, (13 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
The price is NZ$480
includes taxes & fees
16 Nov - 17 Nov
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

14. Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"Our family enjoyed a relaxing weekend before R-day at West Point and it was perfect! A beautiful property and we hope to be back another time!"
United States
Quintina R.
The price is NZ$961
includes taxes & fees
15 Nov - 16 Nov
Chestnut on Willow Lake
A lakeside seating area with Adirondack chairs arranged around a central fire pit.

15. Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!
Fishkill
The price is NZ$708
includes taxes & fees
16 Nov - 17 Nov
Red Cottage - Lakeside Property!
A modern kitchen with a central island, built-in appliances, and a stone accent wall.

16. 3BR Hudson Valley home perfect for families!

3BR Hudson Valley home perfect for families!
Wallkill
10.0 out of 10, Exceptional, (6 reviews)
"This property was lovely and peaceful! We enjoyed the stay in the area! Very clean and neat. Easy to use technology and check-in/out."
United States
Cheryl N.
The price is NZ$930
includes taxes & fees
22 Nov - 23 Nov
3BR Hudson Valley home perfect for families!
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

17. Hudson Valley/West Point Retreat w/ parking!

Hudson Valley/West Point Retreat w/ parking!
Highland Falls
The price is NZ$858
includes taxes & fees
8 Dec - 9 Dec
Hudson Valley/West Point Retreat w/ parking!
A living room with a sofa, a coffee table, a wooden chair, a striped rug, and a wall-mounted wreath.

18. The DeVita House Est. 1900

The DeVita House Est. 1900
Gardiner
10.0 out of 10, Exceptional, (46 reviews)
"The house was in a perfect location! Host was very easy to communicate with!"
United States
Matthew
The price is NZ$799
includes taxes & fees
15 Nov - 16 Nov
The DeVita House Est. 1900
A modern kitchen with white cabinets, stainless steel appliances, and wooden flooring.

19. Luxury 3BR with King Beds in Montgomery Village

Luxury 3BR with King Beds in Montgomery Village
Montgomery
10.0 out of 10, Exceptional, (5 reviews)
"Excellent location! Very clean and the hosts were quick to respond to communication. We would definitely stay here again. "
United States
Barbara M.
The price is NZ$817
includes taxes & fees
15 Nov - 16 Nov
Luxury 3BR with King Beds in Montgomery Village
A fire pit with four Adirondack chairs arranged around it, set on a gravel surface with a lake and trees in the background.

20. Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz

Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
wallkill
9.8 out of 10, Exceptional, (61 reviews)
"Had a wonderful time! Loved our stay at this beautiful river front property!"
United States
Debbie M.
The price is NZ$755
includes taxes & fees
14 Dec - 15 Dec
Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
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

Learn more about New Windsor

Nestled along the Hudson River, this historic town boasts the captivating Storm King Art Centre, where massive sculptures dot rolling hills. Nearby, outdoor enthusiasts can hike the trails of Bear Mountain State Park or explore West Point's prestigious military academy.

See all hotels in New Windsor
A calm lake at sunset with trees and grass along the shore.

Top reviews in New Windsor

A hotel indoor pool with lounge chairs, a hot tub, and a warning sign.
Homewood Suites Stewart Airport

Homewood Suites Stewart Airport

Homewood Suites Stewart Airport
New Windsor

10/10 Excellent

The room was a great size, clean, well maintained and very good in general. The breakfast isn't as good as back home, but the best breakfast with variety that I've had in the States.
Australia
Susanne G
Reviewed June 18, 2017
Homewood Suites Stewart Airport