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

New Windsor Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for New Windsor holiday rentals

Lake view

Jellystone Park Gardiner

Jellystone Park Gardiner
3.0 star property
Gardiner
The price is S$517
includes taxes & fees
7 Jul - 8 Jul
Jellystone Park Gardiner
Interior

Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
3.0 star property
Monroe
10.0 out of 10, Exceptional, (3 reviews)
"fantastic accommodations"
United States
David
The price is S$668
includes taxes & fees
2 Jul - 3 Jul
Hudson Valley Retreat w/ Pool Near Greenwood Lake
View from room

Historic Horse Barn Apartment in Goshen

Historic Horse Barn Apartment in Goshen
4.0 star property
Goshen
The price is S$490
includes taxes & fees
30 Jun - 1 Jul
Historic Horse Barn Apartment in Goshen
Living area

Hay Loft Apartment in Barn - Goshen

Hay Loft Apartment in Barn - Goshen
2.0 star property
Goshen
The price is S$759
includes taxes & fees
29 Jun - 30 Jun
Hay Loft Apartment in Barn - Goshen
Private kitchen

Carriage House Apartment Goshen NY

Carriage House Apartment Goshen NY
4.0 star property
Goshen
The price is S$682
includes taxes & fees
13 Jul - 14 Jul
Carriage House Apartment Goshen NY
7 bedrooms

West Point Summer Pool Jacuzzi Events Pets OK

West Point Summer Pool Jacuzzi Events Pets OK
2.0 star property
Cornwall
The price is S$2,140
includes taxes & fees
29 Jun - 30 Jun
West Point Summer Pool Jacuzzi Events Pets OK
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

SureStay Plus Hotel by Best Western Highland Poughkeepsie

SureStay Plus Hotel by Best Western Highland Poughkeepsie

10/10 Excellent
"Overall, very happy with our stay, will be back. There was a problem with our first room, but the staff and manager fixed the issue and provided another acceptable room. All of the staff that we dealt with were very helpful and accommodating, pleasant to deal with. If you travel a lot, you know that is often not the case. So this was refreshing change! We had a king bed with the sofa couch and found it to be roomy and clean. This was also a great hotel to stay at with a dog. Good value and a pleasant stay!"
Bethany 4-night trip
Posted 1 hour ago
SureStay Plus Hotel by Best Western Highland Poughkeepsie

Explore a world of travel with Expedia

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.

How many holiday rentals are there in New Windsor?

Choose from 10 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 Cantonment State Historic Site and New Windsor Little League.

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.