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

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for New Windsor holiday homes

A modern kitchen with white cabinets, a marble countertop, and a built-in oven.

1. 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 £687
includes taxes & fees
26 Oct - 27 Oct
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.

2. Bright Cornwall-On-Hudson Vacation Rental!

Bright Cornwall-On-Hudson Vacation Rental!
Cornwall-On-Hudson
10.0 out of 10, Exceptional, (35 reviews)
"We had a girlfriend get away long weekend. This was a great house and really convenient location. Two really good restaurants were within walking distance just around the corner. I would highly recommend staying here!"
United States
Dawn H.
The price is £525
includes taxes & fees
22 Nov - 23 Nov
Bright Cornwall-On-Hudson Vacation Rental!
A modern kitchen with white cabinets, a central island, bar stools, and a stainless steel dishwasher.

3. House + Suite · Hudson View Hot Tub

House + Suite · Hudson View Hot Tub
Newburgh
10.0 out of 10, Exceptional, (1 review)
House + Suite · Hudson View Hot Tub
A staircase with red carpeted steps, wooden handrails, and string lights.

4. 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 £419
includes taxes & fees
2 Nov - 3 Nov
Large,Cozy,Bright Apartment, Business Themed.
Room

5. Luxury Hudson Valley Retreat near West Point, Storm King & Beacon

Luxury Hudson Valley Retreat near West Point, Storm King & Beacon
Cornwall
9.0 out of 10, Wonderful, (2 reviews)
"Great House, less than 15 mins to front gate at West Point, convenient location for visiting and enjoying activities at West Point, e.g. football games, cadet events for family members, etc. Hope to be able to stay there again on another visit to the "Rockbound Highland Home"!!! "
United States
Jeff M.
The price is £705
includes taxes & fees
27 Oct - 28 Oct
Luxury Hudson Valley Retreat near West Point, Storm King & Beacon
A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

6. House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
9.8 out of 10, Exceptional, (14 reviews)
"We had a very comfortable stay. Nice quaint village. Area was quiet and easy to get to."
United States
Leann M.
The price is £336
includes taxes & fees
26 Oct - 27 Oct
House on the Babbling Brook- Quiet 2BR + King Bed!
A deck with Adirondack chairs, a fire pit, and a grill.

7. 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 £334
includes taxes & fees
3 Nov - 4 Nov
3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

8. 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 £297
includes taxes & fees
17 Nov - 18 Nov
Fabulous 3bdrm Home w/parking!
A house with a covered porch, stone foundation, and a front door with a wreath.

9. West Point Summer Pool Jacuzzi Events Pets OK

West Point Summer Pool Jacuzzi Events Pets OK
2.0 star property
Cornwall
The price is £948
includes taxes & fees
16 Nov - 17 Nov
West Point Summer Pool Jacuzzi Events Pets OK
An outdoor patio area with a covered seating area, a pool, and potted plants.

10. 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 £254
includes taxes & fees
28 Oct - 29 Oct
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
A bedroom with a bed, a ceiling fan, a nightstand, a window with curtains, and a wall with framed pictures.

11. Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
9.4 out of 10, Exceptional, (8 reviews)
"Great location and super host. "
United States
James U.
The price is £390
includes taxes & fees
1 Nov - 2 Nov
Sleek Escape: Modern 3 BR- 4 Min from West Point !
A blue house with a white porch, a welcome sign, and a mailbox.

12. 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.
The price is £393
includes taxes & fees
26 Oct - 27 Oct
3BR West Point Retreat-3min to Back Gate+ King Bed
A room with a wooden floor, a white door with a number, and a window with blinds.

13. 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 £290
includes taxes & fees
17 Nov - 18 Nov
Lovely 3BR Home with parking-Walk to WP Gate!
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 £408
includes taxes & fees
11 Nov - 12 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 £305
includes taxes & fees
11 Nov - 12 Nov
Red Cottage - Lakeside Property!
Pool

16. complete privacy vacation home [private pool]

complete privacy vacation home [private pool]
Newburgh
9.0 out of 10, Wonderful, (17 reviews)
"oh my god the best place it feels like home"
United States
Phelicia G.
The price is £880
includes taxes & fees
2 Nov - 3 Nov
complete privacy vacation home [private pool]
A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

17. A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail

A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
Wallkill
9.2 out of 10, Wonderful, (18 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
The price is £109
includes taxes & fees
28 Oct - 29 Oct
A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

18. 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 £213
includes taxes & fees
25 Oct - 26 Oct
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

19. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (41 reviews)
"Our stay was very nice and described as listed! We recommend anyone who is interested to stay! "
United States
Aj L.
The price is £317
includes taxes & fees
29 Oct - 30 Oct
Contemporary Cozy Cottage
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 £303
includes taxes & fees
3 Nov - 4 Nov
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.
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Top New Windsor Hotel Reviews

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

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

10/10 Excellent
"The arrival was easy and three lady was awesome! Great customer service"
Ana 2-night trip
Posted 7 hours ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Find out more about New Windsor

New Windsor Holiday Homes information

Number of reviews
332
Accommodation
322 Holiday Homes
Lowest Price
£109
Highest Price
£948