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 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for New Windsor vacation rentals

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

1. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (52 reviews)
"We enjoyed our stay, property was as described. It's convenient to many of the Hudson Valley small towns, including West Point."
United States
Mike W.
$331 nightly
The price is $374
Nov 3 - Nov 4
Total with taxes and fees
Grant - A Tranquil One Bedroom Steps from River
A modern kitchen with grey cabinets, stainless steel appliances, a granite countertop, and a wooden floor.

2. 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.
$213 nightly
The price is $241
Nov 6 - Nov 7
Total with taxes and fees
2-bedroom apartment in excellent Newburgh with AC and charm
A room with a bay window overlooking a lake and autumn foliage, featuring two green armchairs, a small table, and a potted plant.

3. Hudson View Hot Tub · Walk to Waterfront

Hudson View Hot Tub · Walk to Waterfront
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.
$709 nightly
The price is $835
Nov 1 - Nov 2
Total with taxes and fees
Hudson View Hot Tub · Walk to Waterfront
A modern kitchen with white cabinets, a central island with stools, a stainless steel refrigerator, and a staircase leading to another level.

4. Bright Cornwall-On-Hudson Vacation Rental!

Bright Cornwall-On-Hudson Vacation Rental!
Cornwall-On-Hudson
10.0 out of 10, Exceptional, (35 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.
$605 nightly
The price is $715
Nov 22 - Nov 23
Total with taxes and fees
Bright Cornwall-On-Hudson Vacation Rental!
A small, two-story house with a red and gray exterior, a front porch with blue chairs, and a table.

5. Cabin in the heart of the Hudson Valley, Cabin 4

Cabin in the heart of the Hudson Valley, Cabin 4
Newburgh
9.2 out of 10, Wonderful, (31 reviews)
"Everything was just as it was in our past stays. The place was clean, neat and organized very well. Communication with the host was very easy and almost immediate reply."
United States
Albert
$198 nightly
The price is $234
Nov 1 - Nov 2
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 4
A compact living space with a kitchenette, a sofa, a bed, and a colorful rug.

6. 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.
$244 nightly
The price is $288
Nov 2 - Nov 3
Total with taxes and fees
Cabin in the Heart of the Hudson Valley, Cabin 1
A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

7. 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.
$275 nightly
The price is $282
Nov 2 - Nov 3
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

8. 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, (16 reviews)
"Host was available and communicated very well. The house was very clean too."
United States
Erika
House on the Babbling Brook- Quiet 2BR + King Bed!
A cozy living room with a sofa, a dining table, and a bed.

9. Cozy country efficiency in the Hudson Valley

Cozy country 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.
$299 nightly
The price is $353
Nov 1 - Nov 2
Total with taxes and fees
Cozy country efficiency in the Hudson Valley
A brick building with a sign reading 'Lobby' in front.

10. 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
$79 nightly
The price is $91
Nov 23 - Nov 24
Total with taxes and fees
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

11. 1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
9.6 out of 10, Exceptional, (19 reviews)
"Great rooms and service,"
United States
Anonymous traveler
$95 nightly
The price is $107
Nov 14 - Nov 15
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen, Shower
A modern kitchen with stainless steel appliances, wooden cabinets, and a contemporary light fixture.

12. Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Location was perfect for West Point visit. The space was clean and recently updated, the beds very comfortable, and perfect layout and spacious for 3-4 people. The host was welcoming and responsive."
United States
Maria L.
$306 nightly
The price is $343
Nov 17 - Nov 18
Total with taxes and fees
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
A wooden coffee table with two decorative planters in a living room.

13. Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (26 reviews)
"Clean and modern with good amenities. Would stay here again. "
United States
Daniel C.
$335 nightly
The price is $377
Nov 17 - Nov 18
Total with taxes and fees
Walk to WP Gate + Free Parking!
A wooden cabin with a covered deck, outdoor seating, and a fire pit.

14. Historic Cabin with Pool & Fire Pit

Historic Cabin with Pool & Fire Pit
Montgomery
9.8 out of 10, Exceptional, (6 reviews)
"This little cabin was exactly what we needed for our stay in NY. It looks just as described, was clean, and the location was perfect for all of the places we wanted to visit. Overall it was very cozy and relaxing and we can't wait to stay again! "
United States
Sarah A.
$200 nightly
The price is $236
Nov 1 - Nov 2
Total with taxes and fees
Historic Cabin with Pool & Fire Pit
A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

15. 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, (19 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
$127 nightly
The price is $142
Nov 1 - Nov 2
Total with taxes and fees
A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
A house with a view of a bridge and mountains.

16. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (149 reviews)
"We had a great stay!!"
United States
Jasmine
$280 nightly
The price is $331
Nov 2 - Nov 3
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A bedroom with a bed, a ceiling fan, a window, and a painting on the wall.

17. 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.
$432 nightly
The price is $443
Nov 2 - Nov 3
Total with taxes and fees
Local Artist Inspired | Walk to WestPoint + King Bed
A deck with Adirondack chairs, a fire pit, and a grill.

18. 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
$358 nightly
The price is $423
Nov 9 - Nov 10
Total with taxes and fees
3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
Room

19. 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.
Luxury Hudson Valley Retreat near West Point, Storm King & Beacon
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

The Heartwood

The Heartwood

10/10 Excellent
"Excellent, helpful staff and amenities. The room was spotless & very comfortable. The hotel restaurant was top notch: service & the quality of cuisine were also excellent."
Anthony 1-night trip
Posted 8 hours ago
The Heartwood

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 $91 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.