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

New Windsor Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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, (50 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.
$262 nightly
The price is $296
Oct 19 - Oct 20
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.
$215 nightly
The price is $243
Oct 22 - Oct 23
Total with taxes and fees
2-bedroom apartment in excellent Newburgh with AC and charm
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!

Bright Cornwall-on-hudson Vacation Rental!
3.0 star property
Cornwall
10.0 out of 10, Exceptional, (1 review)
"Very nice property, very comfortable, close to multiple sightseeing location including bear mountain."
United States
Poyuk
$591 nightly
The price is $698
Oct 22 - Oct 23
Total with taxes and fees
Bright Cornwall-on-hudson Vacation Rental!
A compact living space with a kitchenette, a sofa, a bed, and a colorful rug.

4. 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.
$204 nightly
The price is $241
Oct 18 - Oct 19
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.

5. Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
10.0 out of 10, Exceptional, (75 reviews)
"Comfy cozy weekend retreat"
United States
Michael M.
$299 nightly
The price is $353
Oct 18 - Oct 19
Total with taxes and fees
Cozy country efficiency in the Hudson Valley
A small blue house with two blue Adirondack chairs, a small table, and a potted plant.

6. Cabin in the heart of the Hudson Valley, Cabin 2

Cabin in the heart of the Hudson Valley, Cabin 2
Newburgh
9.6 out of 10, Exceptional, (41 reviews)
"This was a great place to stay with our cats for a night on our way to Vermont."
United States
George J.
$171 nightly
The price is $202
Oct 18 - Oct 19
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 2
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.
$302 nightly
The price is $311
Oct 18 - Oct 19
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Room

8. 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.
$817 nightly
The price is $965
Oct 27 - Oct 28
Total with taxes and fees
Luxury Hudson Valley Retreat near West Point, Storm King & Beacon
A staircase with red carpeted steps, wooden handrails, and string lights.

9. 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.
$523 nightly
The price is $618
Nov 1 - Nov 2
Total with taxes and fees
Large,Cozy,Bright Apartment, Business Themed.
A staircase with carpeted steps and wooden handrails, leading to a door with glass panels.

10. 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, (13 reviews)
"We had a very comfortable stay. Nice quaint village. Area was quiet and easy to get to."
United States
Leann M.
$404 nightly
The price is $434
Oct 21 - Oct 22
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!
A deck with Adirondack chairs, a fire pit, and a grill.

11. 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, (15 reviews)
"Everything you could ask for!!"
United States
Elisabeth
$369 nightly
The price is $436
Oct 21 - Oct 22
Total with taxes and fees
3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
An aerial view of a lakeside property with a dock, a small building, and several outdoor seating areas.

12. 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
$343 nightly
The price is $390
Nov 6 - Nov 7
Total with taxes and fees
Rustic Cabin in Fishkill!
A house with a view of a bridge and mountains.

13. 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, (148 reviews)
"We had a great stay!!"
United States
Jasmine
$279 nightly
The price is $330
Oct 20 - Oct 21
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

14. Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (12 reviews)
"House was exactly as described. Would stay again."
United States
Beth M.
$278 nightly
The price is $309
Oct 18 - Oct 19
Total with taxes and fees
Fabulous 3bdrm Home w/parking!
A bedroom with a bed, a ceiling fan, a window, and a painting on the wall.

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

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.4 out of 10, Exceptional, (20 reviews)
"Great location! Easy checkin, checkout process. We would stay again"
United States
Morgan S.
$441 nightly
The price is $453
Nov 2 - Nov 3
Total with taxes and fees
Local Artist Inspired | Walk to WestPoint + King Bed
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

16. 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
$79 nightly
The price is $89
Oct 26 - Oct 27
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen, Shower
A wooden coffee table with two decorative planters in a living room.

17. 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.
$255 nightly
The price is $285
Oct 18 - Oct 19
Total with taxes and fees
Walk to WP Gate + Free Parking!
A single-story house with a front porch, two blue chairs, a white chair, and a potted plant with pink flowers.

18. 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, (19 reviews)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
$206 nightly
The price is $243
Oct 19 - Oct 20
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 3
An outdoor patio area with a covered seating area, a pool, and potted plants.

19. Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.2 out of 10, Wonderful, (80 reviews)
"It’s was nice, clean and the outdoor out area was really nice."
United States
Roger S.
$313 nightly
The price is $362
Oct 28 - Oct 29
Total with taxes and fees
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
A brick building with a sign reading 'Lobby' in front.

20. 2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Fishkill
9.2 out of 10, Wonderful, (21 reviews)
"great place tostay"
United States
Anonymous traveler
$87 nightly
The price is $100
Nov 4 - Nov 5
Total with taxes and fees
2 Full Beds | Non-Smoking, Kitchen
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top New Windsor Hotel Reviews

Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

8/10 Good
"good location"
Harry 1-night trip
Posted 9 hours ago
Comfort Suites Fishkill near Interstate 84

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.