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 deck with wicker furniture and a small pool, surrounded by a white fence and trees.

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

New Windsor

CA $736 total

includes taxes & fees

Dec 1 - Dec 2

A modern building with large windows, a brick exterior, and a patio area with a hot tub.

2. Hudson View Hot Tub · Walk to Waterfront

Newburgh

Rachel M.

CA $1,139 total

includes taxes & fees

Nov 15 - Nov 16

A modern kitchen with white cabinetry, a large island, stainless steel appliances, and pendant lighting.

3. Bright Cornwall-On-Hudson Vacation Rental!

Cornwall-On-Hudson

Betty B.

CA $968 total

includes taxes & fees

Nov 22 - Nov 23

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

Newburgh

CA $1,713 total

includes taxes & fees

Nov 15 - Nov 16

A brick wall with a metal container holding a bicycle wheel, a flag, and a potted plant.

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 hardwood flooring, a flat-screen TV on a stand, a white door, and a staircase leading to another level.

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

Highland Falls

Briana T.

CA $511 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 $519 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 $459 total

includes taxes & fees

Nov 16 - Nov 17

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 $382 total

includes taxes & fees

Nov 16 - Nov 17

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 $733 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 $573 total

includes taxes & fees

Nov 15 - Nov 16

A modern living room with a sofa, dining table, and chairs, a kitchen with a stone backsplash, and a fireplace.

16. 3BR Hudson Valley home perfect for families!

Wallkill

Cheryl N.

CA $742 total

includes taxes & fees

Nov 22 - Nov 23

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

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

Highland Falls

CA $683 total

includes taxes & fees

Dec 8 - Dec 9

A white house with a porch, a stone pathway, and a grassy yard.

18. The DeVita House Est. 1900

Gardiner

Matthew

CA $642 total

includes taxes & fees

Nov 15 - Nov 16

A spacious living area with hardwood flooring, a staircase, a round mirror, and a kitchen in the background.

19. Luxury 3BR with King Beds in Montgomery Village

Montgomery

Barbara M.

CA $647 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 $599 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 spacious living area with a curved sofa, a fireplace, and a modern chandelier.

Homewood Suites Stewart Airport

New Windsor

10/10 Excellent

Anonymous traveller

A hotel room with a large bed, two bedside tables, a nightstand, a red throw blanket, a headboard, two wall-mounted lamps, and a window with curtains.

Comfort Suites Fishkill near Interstate 84

Fishkill

10/10 Excellent

Steeve

A large, two-story house with a blue roof, surrounded by lush greenery and a well-maintained lawn.

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