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

New Windsor Holiday Rentals

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Check prices for these dates

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

Our top choices for New Windsor holiday 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.
The price is HK$1,059
HK$2,326 total
includes taxes & fees
19 Oct - 20 Oct
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.
The price is HK$1,483
HK$1,909 total
includes taxes & fees
27 Oct - 28 Oct
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
The price is HK$2,912
HK$5,481 total
includes taxes & fees
22 Oct - 23 Oct
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.
The price is HK$981
HK$1,789 total
includes taxes & fees
18 Oct - 19 Oct
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.
The price is HK$1,452
HK$2,790 total
includes taxes & fees
21 Oct - 22 Oct
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.
The price is HK$903
HK$1,493 total
includes taxes & fees
18 Oct - 19 Oct
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.
The price is HK$887
HK$2,393 total
includes taxes & fees
5 Nov - 6 Nov
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.
The price is HK$3,649
HK$7,574 total
includes taxes & fees
27 Oct - 28 Oct
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.
The price is HK$3,610
HK$4,839 total
includes taxes & fees
4 Nov - 5 Nov
Large,Cozy,Bright Apartment, Business Themed.
A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

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, (14 reviews)
"We had a very comfortable stay. Nice quaint village. Area was quiet and easy to get to."
United States
Leann M.
The price is HK$981
HK$3,173 total
includes taxes & fees
20 Oct - 21 Oct
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, (16 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is HK$1,711
HK$3,421 total
includes taxes & fees
2 Nov - 3 Nov
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
The price is HK$1,968
HK$3,065 total
includes taxes & fees
6 Nov - 7 Nov
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
The price is HK$1,554
HK$2,614 total
includes taxes & fees
28 Oct - 29 Oct
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.
The price is HK$1,209
HK$2,392 total
includes taxes & fees
19 Oct - 20 Oct
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.
The price is HK$1,099
HK$3,544 total
includes taxes & fees
21 Oct - 22 Oct
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 traveller
The price is HK$622
HK$704 total
includes taxes & fees
26 Oct - 27 Oct
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.
The price is HK$1,209
HK$2,236 total
includes taxes & fees
18 Oct - 19 Oct
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, (20 reviews)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
The price is HK$981
HK$1,808 total
includes taxes & fees
19 Oct - 20 Oct
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.
The price is HK$2,158
HK$2,840 total
includes taxes & fees
28 Oct - 29 Oct
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 traveller
The price is HK$684
HK$791 total
includes taxes & fees
1 Nov - 2 Nov
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.
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Top New Windsor Hotel Reviews

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

10/10 Excellent
"Bear Mountain Inn is a unique and beautiful retreat in the heart of the Hudson Valley. We go for the scenery, hiking, and watching the marine and rail traffic along the Hudson River. Staff is always helpful. We booked 2 nights but could only. stay 1 due to a family emergency and the staff worked with Expedia to refund the 2nd night. Will definitely return as we love the atmosphere. Stayed in 1 of the stone cottages in the woods above the lake. Basic room with a shared common area and outdoor porch/deck. Room had a small refrigerator and TV with local channels. Clean and quiet and what you'd expect in a state or national park setting. Great 1.5 mile paved walking trail below the cottage that circles the picturesque lake on the property grounds. Nice way to start the day."
Robert K 2-night trip
Posted 20 hours ago
Overlook Lodge at Bear Mountain

Find out more about New Windsor

Search for holiday rentals in New Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in New Windsor using one of the methods below:

  • View our selection of featured holiday rentals in New Windsor
  • Use the map to find apartments and other holiday homes in the New Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in New Windsor while they last

Look no further and take a look at our great range of rental properties in New Windsor!

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.