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

Holiday Homes in New Windsor

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for New Windsor holiday homes

A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

1. 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, (12 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 AU$565
includes taxes & fees
28 Sept - 29 Sept
House on the Babbling Brook- Quiet 2BR + King Bed!
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.
The price is AU$986
includes taxes & fees
22 Oct - 23 Oct
Bright Cornwall-On-Hudson Vacation Rental!
A room with a large bay window, two green armchairs, a small round table, a white sofa, and a potted plant.

3. River Views & Hot Tub | Riverview on Washington

River Views & Hot Tub | Riverview on Washington
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 AU$1,139
includes taxes & fees
29 Sept - 30 Sept
River Views & Hot Tub | Riverview on Washington
A deck with Adirondack chairs, a fire pit, and a grill.

4. 3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Cornwall
10.0 out of 10, Exceptional, (15 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is AU$629
includes taxes & fees
6 Oct - 7 Oct
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
A bedroom with a bed, a ceiling fan, a nightstand, a window with curtains, and a wall with framed pictures.

5. 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 AU$632
includes taxes & fees
29 Sept - 30 Sept
Sleek Escape: Modern 3 BR- 4 Min from West Point !
An outdoor patio area with a covered seating area, a pool, and potted plants.

6. 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 AU$487
includes taxes & fees
30 Sept - 1 Oct
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
A deck with wicker furniture, a bench, and a table.

7. River Views & Hot Tub | Artisan on Washington

River Views & Hot Tub | Artisan on Washington
Newburgh
10.0 out of 10, Exceptional, (1 review)
River Views & Hot Tub | Artisan on Washington

8. 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 AU$1,464
includes taxes & fees
29 Sept - 30 Sept
Luxury Hudson Valley Retreat near West Point, Storm King & Beacon
A modern kitchen with grey cabinets, a central island, bar stools, and a stainless steel range hood.

9. Perfect and Spacious Hudson Valley Escape!

Perfect and Spacious Hudson Valley Escape!
Cornwall
8.0 out of 10, Very good, (3 reviews)
"Great host, very responsive and accommodating. The house was very clean and comfortable."
United States
Joseph S.
The price is AU$1,143
includes taxes & fees
28 Sept - 29 Sept
Perfect and Spacious Hudson Valley Escape!
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 AU$618
includes taxes & fees
30 Sept - 1 Oct
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 AU$666
includes taxes & fees
28 Oct - 29 Oct
Fabulous 3bdrm Home w/parking!
A house with a covered porch, stone foundation, and a front door with a wreath.

12. West Point Summer Pool Jacuzzi Events Pets OK

West Point Summer Pool Jacuzzi Events Pets OK
2.0 star property
Cornwall
The price is AU$2,034
includes taxes & fees
4 Oct - 5 Oct
West Point Summer Pool Jacuzzi Events Pets OK
A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

13. 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, (15 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
The price is AU$184
includes taxes & fees
29 Sept - 30 Sept
A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
A modern kitchen with granite countertops, dark cabinetry, and a built-in island with bar stools.

14. 3BR Hudson Valley home perfect for families!

3BR Hudson Valley home perfect for families!
Wallkill
10.0 out of 10, Exceptional, (5 reviews)
"A friend and I needed to book a last minute stay. This house exceeded our expectations. It was clean and comfortable and had everything we needed. It was a great location as well!"
United States
Rachel S.
The price is AU$773
includes taxes & fees
28 Sept - 29 Sept
3BR Hudson Valley home perfect for families!
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 AU$398
includes taxes & fees
28 Sept - 29 Sept
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A fire pit with four Adirondack chairs arranged around it, set on a gravel surface with a lake and trees in the background.

16. 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.
The price is AU$565
includes taxes & fees
29 Sept - 30 Sept
Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz

17. 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 AU$1,631
includes taxes & fees
28 Sept - 29 Sept
complete privacy vacation home [private pool]
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

18. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (40 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 AU$588
includes taxes & fees
30 Sept - 1 Oct
Contemporary Cozy Cottage
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, (4 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 AU$718
includes taxes & fees
28 Sept - 29 Sept
Luxury 3BR with King Beds in Montgomery Village
A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

20. Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
United States
Doria W.
The price is AU$1,023
includes taxes & fees
28 Sept - 29 Sept
Chestnut on Willow Lake
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

Inn on the Hudson

Inn on the Hudson

8/10 Good
"Clean rooms and parking was easy"
Lloyd 5-night trip
Posted 1 hour ago
Inn on the Hudson

Find out more about New Windsor

New Windsor Holiday Homes information

Number of reviews
329
Accommodation
321 Holiday Homes
Lowest Price
AU$184
Highest Price
AU$2,034