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

Holiday Rentals in New Windsor

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Our top choices for New Windsor holiday rentals

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
The price is €444
includes taxes & fees
15 Dec - 16 Dec
NEW! Cozy 3BR Home Near West Point & Hudson Valley - King Bed

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.
The price is €325
includes taxes & fees
8 Dec - 9 Dec
Grant - A Tranquil One Bedroom Steps from River

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
The price is €222
includes taxes & fees
23 Nov - 24 Nov
Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer

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.
The price is €214
includes taxes & fees
22 Nov - 23 Nov
2-bedroom apartment in excellent Newburgh with AC and charm

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.
The price is €257
includes taxes & fees
1 Dec - 2 Dec
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

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.
Bright Cornwall-On-Hudson Vacation Rental!

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.
The price is €218
includes taxes & fees
16 Nov - 17 Nov
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

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.
The price is €227
includes taxes & fees
3 Dec - 4 Dec
Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer

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.
The price is €252
includes taxes & fees
15 Nov - 16 Nov
Cabin in the heart of the Hudson Valley, Cabin 3

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.
The price is €252
includes taxes & fees
15 Nov - 16 Nov
Cabin in the Heart of the Hudson Valley, Cabin 1

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.
The price is €328
includes taxes & fees
15 Nov - 16 Nov
Cozy, rustic efficiency in the Hudson Valley

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

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 traveller
The price is €72
includes taxes & fees
10 Dec - 11 Dec
1 King Bed | Non-Smoking, Kitchen, Shower

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 traveller
The price is €82
includes taxes & fees
29 Nov - 30 Nov
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

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.
The price is €483
includes taxes & fees
23 Nov - 24 Nov
Large,Cozy,Bright Apartment, Business Themed.

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
The price is €339
includes taxes & fees
21 Nov - 22 Nov
Rustic Cabin in Fishkill!

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

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.
The price is €378
includes taxes & fees
15 Nov - 16 Nov
Local Artist Inspired | Walk to WestPoint + King Bed

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
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

Find out more about New Windsor

Everything you need to know about New Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the New Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

New Windsor holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A New Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of New Windsor holiday rentals we have selected for you start as low as €82 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on New Windsor rentals

At Expedia, we put the best New Windsor holiday 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 holiday.

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. 

Frequently asked questions

Can I find a holiday rental in New Windsor?

Yes, there are holiday rentals close to the most popular sights in New Windsor, or you can select a more 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 coffee shops during your visit.

What are some of the best holiday rentals that New Windsor has to offer?

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: This holiday home rental outside of New Windsor is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in New Windsor?

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

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 holiday rentals like in New Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in New Windsor. Holiday rentals feature extras like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from public hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for family trips.