A large suspension bridge at night with illuminated cables and a central tower.

New Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for New Windsor vacation rentals

A house with a covered porch, stone foundation, and a front door with a wreath.

1. West Point Summer Pool Jacuzzi Events Pets OK

West Point Summer Pool Jacuzzi Events Pets OK
2.0 star property
Cornwall
The price is P41,433
P83,801 total
includes taxes & fees
Sep 9 - Sep 10
West Point Summer Pool Jacuzzi Events Pets OK
A two-story house with a porch, a table, and chairs outside.

2. Historic Horse Barn Apartment in Goshen

Historic Horse Barn Apartment in Goshen
4.0 star property
Goshen
The price is P21,569
P26,557 total
includes taxes & fees
Oct 3 - Oct 4
Historic Horse Barn Apartment in Goshen
A modern hotel room with a large bed, a desk, a chair, a TV, and a view of the outside.

3. Cottage Suites

Cottage Suites
3.0 star property
Middletown
6.0 out of 10, (11 reviews)
"Room could have actually been cleaned , this is a building not a “hotel” ,"
United States
Jennifer
The price is P4,389
P9,562 total
includes taxes & fees
Sep 9 - Sep 10
Cottage Suites
A spacious loft with a high ceiling, exposed beams, a kitchen with modern appliances, a dining area, and a living room with a large sofa.

4. Hay Loft Apartment in Barn - Goshen

Hay Loft Apartment in Barn - Goshen
2.0 star property
Goshen
10.0 out of 10, Exceptional, (1 review)
The price is P24,266
P29,877 total
includes taxes & fees
Oct 3 - Oct 4
Hay Loft Apartment in Barn - Goshen
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

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

10/10 Excellent
"Great parking for our truck and trailer. Wifi was good which was helpful"
Terri 1-night trip
Posted 3 hours ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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
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  • 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 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.

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 National Purple Heart Hall of Honor and Knox's Headquarters State Historic Site. Other places in town to visit include New Windsor Cantonment State Historic Site and New Windsor Little League.

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.