46+ Vacation Rentals & Holiday Homes in New Windsor |
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New Windsor Accommodations - Hotels & Rentals

About New Windsor Vacation Rentals

Discover More than 46 Incredible Getaway Rentals Available in New Windsor. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in New Windsor.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in New Windsor, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in New Windsor. The Average Size of Places to Stay Near New Windsor is 605.21 ft², with Prices Averaging US $519 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in New Windsor. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in New Windsor

Type Count
Vacation Homes 21
Cottages 6
Holiday Apartments 4
Villas 3

Use these Quick Filters to Find a Vacation Rental in New Windsor

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in New Windsor with Online Reservations.

Weather in New Windsor, NY

View the weather forecast for New Windsor before booking your New Windsor Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Activities New WindsorGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World New WindsorGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


National Purple Heart Hall of Honor
Kristi Babcock Memorial Park
New Windsor Cantonment State Historic Site
Knox's Headquarters State Historic Site
Horizon Family Medical Group
Woodbury Common Premium Outlets
Bear Mountain State Park
United States Military Academy
Marist College
Vassar College
Culinary Institute of America
State University of New York-New Paltz
Dia Beacon
Storm King Art Center
Minnewaska State Park
Mount Peter Ski Area
Brotherhood Winery
SplashDown Beach
Harriman State Park

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Vails Gate 71 Properties
National Purple Heart Hall of Honor 66 Properties
New Windsor Cantonment State Historic Site 66 Properties
Horizon Family Medical Group 59 Properties
Knox's Headquarters State Historic Site 50 Properties
Kristi Babcock Memorial Park 41 Properties

Frequently Asked Questions About New Windsor?

What are the top hotels, lake houses & vacation rentals in New Windsor?

We provide an array of great vacation destinations in New Windsor. If you are looking to stay in or around the New Windsor area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in New Windsor:

Which hotel, lake house, or vacation rental in New Windsor is best for families?

Searching for a family-friendly getaway in New Windsor? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in New Windsor?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 46 in the New Windsor area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in New Windsor.


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