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

Holiday Homes in New Windsor

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

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.
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, (34 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.
Bright Cornwall-On-Hudson Vacation Rental!
A staircase with red carpeted steps, wooden handrails, and string lights.

3. 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 €542
includes taxes & fees
11 Nov - 12 Nov
Large,Cozy,Bright Apartment, Business Themed.
Room

4. 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.
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.

5. 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, (13 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 €387
includes taxes & fees
12 Oct - 13 Oct
House on the Babbling Brook- Quiet 2BR + King Bed!
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, (15 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is €420
includes taxes & fees
11 Nov - 12 Nov
3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
A bedroom with a bed, a ceiling fan, a nightstand, a window with curtains, and a wall with framed pictures.

7. 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 €416
includes taxes & fees
2 Nov - 3 Nov
Sleek Escape: Modern 3 BR- 4 Min from West Point !
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, (78 reviews)
"It’s was nice, clean and the outdoor out area was really nice."
United States
Roger S.
The price is €323
includes taxes & fees
28 Oct - 29 Oct
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
A blue house with a white porch, a welcome sign, and a mailbox.

9. 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 €469
includes taxes & fees
12 Oct - 13 Oct
3BR West Point Retreat-3min to Back Gate+ King Bed
A house with a covered porch, stone foundation, and a front door with a wreath.

10. West Point Summer Pool Jacuzzi Events Pets OK

West Point Summer Pool Jacuzzi Events Pets OK
2.0 star property
Cornwall
The price is €1,899
includes taxes & fees
16 Oct - 17 Oct
West Point Summer Pool Jacuzzi Events Pets OK
A room with a wooden floor, a white door with a number, and a window with blinds.

11. 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 €379
includes taxes & fees
11 Nov - 12 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.

12. 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 €393
includes taxes & fees
2 Nov - 3 Nov
Fabulous 3bdrm Home w/parking!
Pool

13. 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.
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.

14. 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, (17 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
The price is €123
includes taxes & fees
3 Nov - 4 Nov
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.

15. 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 €258
includes taxes & fees
12 Oct - 13 Oct
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.

16. Hickory on Willow Lake

Hickory on Willow Lake
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"Clean, quiet and great location. Beautiful property."
United States
Sheila B.
Hickory on Willow Lake
A fire pit with four Adirondack chairs arranged around it, set on a gravel surface with a lake and trees in the background.

17. 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, (60 reviews)
"Had a wonderful time! Loved our stay at this beautiful river front property!"
United States
Debbie M.
Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
A modern kitchen with white cabinets, stainless steel appliances, and wooden flooring.

18. 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.
Luxury 3BR with King Beds in Montgomery Village
A hallway with wooden flooring, white walls, and doors with brass handles.

19. Spacious 4BR/2BT Hiking trails, Lake, Legoland & Warwick

Spacious 4BR/2BT Hiking trails, Lake, Legoland & Warwick
Monroe
The price is €12,010
includes taxes & fees
21 Oct - 22 Oct
Spacious 4BR/2BT Hiking trails, Lake, Legoland & Warwick
A room with a chandelier, a sofa, a table, and a cabinet.

20. Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
8.8 out of 10, Excellent, (23 reviews)
"Great value and beautiful room and In ."
United States
Paul E.
The price is €151
includes taxes & fees
19 Oct - 20 Oct
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
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

8/10 Good
"The place was clean and the breakfast good. It was quite expensive though."
Connie 1-night trip
Posted 4 hours ago
Holiday Inn Express Poughkeepsie by IHG

Find out more about New Windsor

New Windsor Holiday Homes information

Number of reviews
271
Accommodation
321 Holiday Homes
Lowest Price
€123
Highest Price
€1,899