New Windsor Vacation Home Rentals from CA $102: Search Top Private Vacation Homes for Rent

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Our top choices for New Windsor vacation 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 Windsor

CA $717 total

includes taxes & fees

Nov 18 - Nov 19

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

Newburgh

Rachel M.

CA $1,134 total

includes taxes & fees

Nov 18 - Nov 19

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!

Cornwall-On-Hudson

Betty B.

CA $968 total

includes taxes & fees

Nov 22 - Nov 23

A deck with wicker furniture and a view of a lake and mountains.

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

Newburgh

CA $1,705 total

includes taxes & fees

Nov 19 - Nov 20

A staircase with red carpeted steps, wooden handrails, and string lights.

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

Newburgh

Adhith P.

CA $838 total

includes taxes & fees

Dec 7 - Dec 8

A deck with Adirondack chairs, a fire pit, and a grill.

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

Cornwall

Elisabeth

CA $622 total

includes taxes & fees

Nov 16 - Nov 17

A blue house with a white porch, a welcome sign, and a mailbox.

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

Highland Falls

Christine T.

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

Fishkill

Sara

CA $466 total

includes taxes & fees

Nov 15 - Nov 16

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

Wallkill

Carrie

CA $189 total

includes taxes & fees

Nov 15 - Nov 16

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!

Highland Falls

Briana T.

CA $508 total

includes taxes & fees

Dec 8 - Dec 9

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!

Highland Falls

Beth M.

CA $517 total

includes taxes & fees

Dec 8 - Dec 9

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!

Highland Falls

CA $482 total

includes taxes & fees

Nov 18 - Nov 19

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

Hopewell Junction

Peter W.

CA $364 total

includes taxes & fees

Nov 13 - Nov 14

A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

14. Chestnut on Willow Lake

Fishkill

Quintina R.

CA $729 total

includes taxes & fees

Nov 13 - Nov 14

A lakeside seating area with Adirondack chairs arranged around a central fire pit.

15. Red Cottage - Lakeside Property!

Fishkill

CA $544 total

includes taxes & fees

Nov 17 - Nov 18

A modern kitchen with a central island, built-in appliances, and a stone accent wall.

16. 3BR Hudson Valley home perfect for families!

Wallkill

Cheryl N.

CA $739 total

includes taxes & fees

Dec 2 - Dec 3

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

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

Highland Falls

CA $680 total

includes taxes & fees

Dec 8 - Dec 9

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

Gardiner

Matthew

CA $642 total

includes taxes & fees

Nov 15 - Nov 16

A modern kitchen with white cabinets, stainless steel appliances, and wooden flooring.

19. Luxury 3BR with King Beds in Montgomery Village

Montgomery

Barbara M.

CA $644 total

includes taxes & fees

Nov 15 - Nov 16

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

wallkill

Debbie M.

CA $596 total

includes taxes & fees

Dec 7 - Dec 8

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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

New Windsor

10/10 Excellent

Anonymous traveller

A spacious lobby with a high ceiling, a reception desk, a seating area with blue sofas and armchairs, and a visible Pepsi refrigerator.

Comfort Suites Fishkill near Interstate 84

Fishkill

10/10 Excellent

Steeve

A brick building with a covered patio area featuring outdoor seating and string lights.

Cromwell Manor Inn

Cornwall

10/10 Excellent

Cromwell Manor Inn is a beautiful converted mansion built in the 1760s in upstate New York. Right across from summer camps and nature walks, the peaceful natural environment is like having a front row seat to a nature show. The grounds are beautiful, with mature trees, soft grass, and beautiful flowers. It is like something out of a historical painting. During our stay, we were hosted in a blue guest house just at the entrance of the drive. I imagine it must have been the caretaker's residence...

Cynthia Louise