New Windsor Vacation Rentals from AED 385: Search Short-Term Rentals

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Our top choices for New Windsor vacation rentals

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

AED 1,814 total

includes taxes & fees

15 Nov - 16 Nov

A living room with a fireplace, a painting, shelves with decorative items, and a television.

2. Grant - A Tranquil One Bedroom Steps from River

Newburgh

Martha Z.

AED 1,313 total

includes taxes & fees

15 Nov - 16 Nov

A modern bedroom with a blue sofa, a bed, a TV, and a window with a view.

3. Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer

Beacon

Maryanne

AED 892 total

includes taxes & fees

23 Nov - 24 Nov

A modern kitchen with grey cabinets, stainless steel appliances, a granite countertop, and a wooden floor.

4. 2-bedroom apartment in excellent Newburgh with AC and charm

Newburgh

Nick L.

AED 852 total

includes taxes & fees

22 Nov - 23 Nov

A brick building with a storefront featuring a sign for 'LUXE Optique'.

5. Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Beacon

Kelena B.

AED 1,053 total

includes taxes & fees

1 Dec - 2 Dec

A modern kitchen with white cabinets, a central island with stools, a stainless steel refrigerator, and a staircase leading to another level.

6. Bright Cornwall-On-Hudson Vacation Rental!

Cornwall-On-Hudson

Betty B.

AED 2,495 total

includes taxes & fees

22 Nov - 23 Nov

A room with a glass table and chairs, a flat-screen TV on the wall, and a view of a beach and buildings.

7. Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Beacon

Tim B.

AED 871 total

includes taxes & fees

16 Nov - 17 Nov

8. Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer

Beacon

Brendas S.

AED 901 total

includes taxes & fees

3 Dec - 4 Dec

A single-story house with a front porch, two blue chairs, a white chair, and a potted plant with pink flowers.

9. Cabin in the heart of the Hudson Valley, Cabin 3

Newburgh

Bill W.

AED 1,007 total

includes taxes & fees

15 Nov - 16 Nov

A compact living space with a kitchenette, a sofa, a bed, and a colorful rug.

10. Cabin in the Heart of the Hudson Valley, Cabin 1

Newburgh

Tim G.

AED 1,007 total

includes taxes & fees

15 Nov - 16 Nov

A cozy living room with a sofa, a dining table, and a bed.

11. Cozy, rustic efficiency in the Hudson Valley

Newburgh

Frances N.

AED 1,310 total

includes taxes & fees

14 Nov - 15 Nov

A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

12. Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Highland Falls

Andrew L.

AED 1,027 total

includes taxes & fees

17 Nov - 18 Nov

A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

13. 1 King Bed | Non-Smoking, Kitchen, Shower

Fishkill

Anonymous traveler

AED 291 total

includes taxes & fees

8 Dec - 9 Dec

A brick building with a sign reading 'Lobby' in front.

14. Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

Fishkill

Anonymous traveler

AED 331 total

includes taxes & fees

3 Dec - 4 Dec

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

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

Newburgh

Adhith P.

AED 2,161 total

includes taxes & fees

6 Dec - 7 Dec

An aerial view of a lakeside property with a dock, a small building, and several outdoor seating areas.

16. Rustic Cabin in Fishkill!

Fishkill

Joseph

AED 1,345 total

includes taxes & fees

21 Nov - 22 Nov

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

17. 3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

Cornwall

Elisabeth

A living room with a sectional sofa, a coffee table, and a ceiling fan.

18. Local Artist Inspired | Walk to WestPoint + King Bed

Highland Falls

Morgan S.

AED 1,534 total

includes taxes & fees

15 Nov - 16 Nov

Step up to a warm welcome - our charming entryway, complete with a hanging birdhouse, sets the tone for a peaceful stay.

19. Walk-to-Lake Cottage With Grill for Peaceful Fall Days

Putnam Valley

Lisa

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Find vacation rentals that suit your style

Top New Windsor Hotel Reviews

A hotel indoor pool with lounge chairs, a hot tub, and a warning sign.

Homewood Suites Stewart Airport

New Windsor

10/10 Excellent

Needed a place to stay when moving to the area. This hotel was conveniently located and very affordable - especially considering what you get! The suites were fantastic - spacious, everything we needed, kitchenettes. On top of that they serve a good hot breakfast every morning and a manager's reception (which is essentially a meal) four nights a week. What a deal! Friendly, helpful staff too. I truly don't have anything negative to say about this hotel.

Anonymous traveler

A Red Roof Inn & Suites building with a two-story structure, a balcony, and an American flag.

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

New Windsor

10/10 Excellent

Belinda

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

Laura

A balcony with outdoor seating, a staircase, and a view of the cityscape.

The Dutchess Inn and Spa at Beacon

Beacon

10/10 Excellent

Marjorie

A hotel room with a green sofa, a small table, a bed with a headboard, a desk with a lamp, and a framed picture on the wall.

Quality Inn & Suites Fishkill South near I-84

Fishkill

10/10 Excellent

Lynn

A modern hotel room with a large bed, a sitting area with a sofa, a small table, a TV, and a bathtub.

The Factory

Beacon

10/10 Excellent

JAYANTI

An outdoor patio area with a stone fire pit, seating, and a Marriott sign in the background.

SpringHill Suites by Marriott Fishkill

Fishkill

10/10 Excellent

MICHELLE

A Courtyard Marriott hotel with a covered entrance, outdoor seating area, and multiple balconies.

Courtyard by Marriott Newburgh Stewart Airport

Newburgh

10/10 Excellent

Michelle

A lobby with a grand chandelier, two large arched windows, and a central fireplace with a portrait above it.

The Thayer Hotel at West Point

West Point

10/10 Excellent

Amy

A patio area with outdoor seating and a fire pit, surrounded by buildings with a brick facade and a covered seating area.

Best Western Fishkill Inn & Suites

Fishkill

10/10 Excellent

MHD Amar

An outdoor seating area with stone walls, a fire feature, and yellow chairs.

Home2 Suites By Hilton Poughkeepsie

Poughkeepsie

10/10 Excellent

Comfy. Homey. Clean. Brightly lit and cheery lobby area. Great breakfast setup. Nice bedding. Spacious suite style. Easy and quick drive to Marist. Very small downers: Parking lot a tad cramped and narrow. Muddy construction lot in front. Desk staff tends to stray away from the desk and there was no telling when they would be back. Could use a desk sign or something saying "Back in 15 minutes."

David

A hotel entrance with stone pillars, a covered walkway, and a bench.

Sleep Inn & Suites Monroe - Woodbury

Monroe

10/10 Excellent

Lisyani

Frequently Asked Questions

Can I find a vacation rental in New Windsor?

Yes, we have vacation rentals near the most popular local attractions in New Windsor, or you can select a secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in New Windsor. Allow lots of time to check out the lakeside and coffeehouses during your visit.

What's the top vacation rental in New Windsor?

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: Visitors like this New Windsor vacation home rental. It is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in New Windsor?

Choose from 9 Expedia vacation rentals in New Windsor for a memorable vacation.

What can I see and do in New Windsor?

Cultural attractions to visit include Knox's Headquarters State Historic Site and National Purple Heart Hall of Honor. Other places in town to visit include New Windsor Little League and New Windsor Cantonment State Historic Site.

What are vacation rentals like in New Windsor?

Vacation rentals are private accommodations you can stay in for a short or long stay in New Windsor. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from public hotel elevators and busy reception areas while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family trip or a small group gathering.

New Windsor Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for New Windsor vacation rentals

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

2. Grant - A Tranquil One Bedroom Steps from River

3. Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer

4. 2-bedroom apartment in excellent Newburgh with AC and charm

5. Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

6. Bright Cornwall-On-Hudson Vacation Rental!

7. Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

8. Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer

9. Cabin in the heart of the Hudson Valley, Cabin 3

10. Cabin in the Heart of the Hudson Valley, Cabin 1

11. Cozy, rustic efficiency in the Hudson Valley

12. Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

13. 1 King Bed | Non-Smoking, Kitchen, Shower

14. Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

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

16. Rustic Cabin in Fishkill!

17. 3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

18. Local Artist Inspired | Walk to WestPoint + King Bed

19. Walk-to-Lake Cottage With Grill for Peaceful Fall Days

Find vacation rentals that suit your style

Top New Windsor Hotel Reviews

Homewood Suites Stewart Airport

10/10 Excellent

Frequently Asked Questions

Can I find a vacation rental in New Windsor?

What's the top vacation rental in New Windsor?

How many vacation rentals are there in New Windsor?

What can I see and do in New Windsor?

What are vacation rentals like in New Windsor?