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

New Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

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! Cozy 3BR Home Near West Point & Hudson Valley - King Bed
New Windsor
$413 nightly
The price is $488
Nov 16 - Nov 17
Total with taxes and fees
NEW! Cozy 3BR Home Near West Point & Hudson Valley - King Bed
A living room with a fireplace, a painting, shelves with decorative items, and a television.

2. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (53 reviews)
"Beautiful little apartment, walking to shops and easy parking"
United States
Martha Z.
$316 nightly
The price is $357
Nov 15 - Nov 16
Total with taxes and fees
Grant - A Tranquil One Bedroom Steps from River
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

Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
Beacon
10.0 out of 10, Exceptional, (57 reviews)
"Great location. Very walkable. Highly recommend."
United States
Maryanne
$211 nightly
The price is $243
Nov 23 - Nov 24
Total with taxes and fees
Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
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

2-bedroom apartment in excellent Newburgh with AC and charm
Newburgh
10.0 out of 10, Exceptional, (3 reviews)
"We have stayed here once before overnight while in the area for an event. It is close to where we needed to be and a great value for the price"
United States
Nick L.
$205 nightly
The price is $232
Nov 22 - Nov 23
Total with taxes and fees
2-bedroom apartment in excellent Newburgh with AC and charm
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

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Beacon
9.8 out of 10, Exceptional, (59 reviews)
"Great location, comfortable spot to sleep in after being out all day."
United States
Kelena B.
$249 nightly
The price is $287
Dec 1 - Dec 2
Total with taxes and fees
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
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!

Bright Cornwall-On-Hudson Vacation Rental!
Cornwall-On-Hudson
10.0 out of 10, Exceptional, (35 reviews)
"Very comfortable house and great location."
United States
Betty B.
$575 nightly
The price is $679
Nov 22 - Nov 23
Total with taxes and fees
Bright Cornwall-On-Hudson Vacation Rental!
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

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Beacon
10.0 out of 10, Exceptional, (41 reviews)
"Great location very walkable"
United States
Tim B.
$206 nightly
The price is $237
Nov 16 - Nov 17
Total with taxes and fees
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
A brick building with a storefront featuring a sign for 'LUXE Optique'.

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

Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer
Beacon
10.0 out of 10, Exceptional, (63 reviews)
"It was a convenient location to downtown."
United States
Brendas S.
$213 nightly
The price is $245
Dec 3 - Dec 4
Total with taxes and fees
Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer
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

Cabin in the heart of the Hudson Valley, Cabin 3
Newburgh
9.8 out of 10, Exceptional, (20 reviews)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
$232 nightly
The price is $274
Nov 15 - Nov 16
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 3
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

Cabin in the Heart of the Hudson Valley, Cabin 1
Newburgh
10.0 out of 10, Exceptional, (36 reviews)
"Great place! Nicely decorated with attention to detail. My wife and I would stay again if we are back in the area."
United States
Tim G.
$232 nightly
The price is $274
Nov 15 - Nov 16
Total with taxes and fees
Cabin in the Heart of the Hudson Valley, Cabin 1
A cozy living room with a sofa, a dining table, and a bed.

11. Cozy, rustic efficiency in the Hudson Valley

Cozy, rustic efficiency in the Hudson Valley
Newburgh
10.0 out of 10, Exceptional, (75 reviews)
"Lovely cottage in a beautiful setting with everything you need to rest, relax, and enjoy this lovely part of New York state. Highly recommend!"
United States
Frances N.
$302 nightly
The price is $357
Nov 15 - Nov 16
Total with taxes and fees
Cozy, rustic efficiency in the Hudson Valley
A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

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

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.2 out of 10, Wonderful, (25 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
$266 nightly
The price is $270
Nov 15 - Nov 16
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

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

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
9.6 out of 10, Exceptional, (20 reviews)
"Great rooms and service,"
United States
Anonymous traveler
$70 nightly
The price is $79
Dec 11 - Dec 12
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen, Shower
A brick building with a sign reading 'Lobby' in front.

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

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.0 out of 10, Wonderful, (21 reviews)
"Great place to stay,"
United States
Anonymous traveler
$78 nightly
The price is $90
Nov 29 - Nov 30
Total with taxes and fees
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
A staircase with red carpeted steps, wooden handrails, and string lights.

15. 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.
$448 nightly
The price is $529
Nov 23 - Nov 24
Total with taxes and fees
Large,Cozy,Bright Apartment, Business Themed.
An aerial view of a lakeside property with a dock, a small building, and several outdoor seating areas.

16. Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"Clean rooms, Diner down the block, family friendly, communication was prompt and clear"
United States
Joseph
$322 nightly
The price is $366
Nov 21 - Nov 22
Total with taxes and fees
Rustic Cabin in Fishkill!
A deck with Adirondack chairs, a fire pit, and a grill.

17. 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, (16 reviews)
"Everything you could ask for!!"
United States
Elisabeth
3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
A modern kitchen with stainless steel appliances, white cabinetry, a coffee station, and a dining area with a wooden table and bench.

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

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.6 out of 10, Exceptional, (21 reviews)
"Great location! Easy checkin, checkout process. We would stay again"
United States
Morgan S.
$405 nightly
The price is $411
Nov 15 - Nov 16
Total with taxes and fees
Local Artist Inspired | Walk to WestPoint + King Bed
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

Walk-to-Lake Cottage With Grill for Peaceful Fall Days
Putnam Valley
9.8 out of 10, Exceptional, (25 reviews)
"Absolute comfortable stay. Everything you need and fantastic host!! Will be back."
United States
Lisa
$472 nightly
The price is $521
Nov 15 - Nov 16
Total with taxes and fees
Walk-to-Lake Cottage With Grill for Peaceful Fall Days
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

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

8/10 Good
"The room was clean. Staff was super helpful and the breakfast area was huge with lots of options."
Arlene 2-night trip
Posted less than an hour ago
La Quinta Inn & Suites by Wyndham Middletown-Goshen

Find out more about New Windsor

Everything you need to know about New Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the New Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect New Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

New Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in New Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit New Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $90 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on New Windsor rentals

At Expedia, we put the best New Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top New Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream New Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around New Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.