Compare New Windsor Villas

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Villas in New Windsor

7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

Monroe NY
Guests of this villa enjoy features like an outdoor pool, a hot tub, and laundry facilities. This smoke-free villa also has barbecue grills.
Pool
Hot Tub
Luxury 10BR Escape w/ Pool, Hot Tub & Game Lounge

Luxury 10BR Escape w/ Pool, Hot Tub & Game Lounge

Stony Point NY
Guests of this villa enjoy features like an outdoor pool, a hot tub, and an arcade/game room. Other amenities at this family-friendly villa include laundry facilities, a garden, and barbecue grills.
Pool
Hot Tub
Warm Escape, Wood Stove, HotTub, Pets, <1 Hr NYC

Warm Escape, Wood Stove, HotTub, Pets, <1 Hr NYC

Harriman NY
At this villa, guests have access to an arcade/game room, laundry facilities, and barbecue grills. This family-friendly villa also has a garden.
Pool
Kitchen
The Scenic Mansion With Breathtaking View

The Scenic Mansion With Breathtaking View

Highland NY
Guests staying at this villa enjoy free WiFi in public areas, laundry facilities, and barbecue grills.
Pool
Kitchen
Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY.

Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY.

2 out of 5
Monroe NY
Guests staying at this villa enjoy a hot tub, laundry facilities, and barbecue grills.
Pool
Hot Tub
Grand 9BR Retreat w/Pool & Hot Tub

Grand 9BR Retreat w/Pool & Hot Tub

Chester NY
Guests of this villa enjoy features like an outdoor pool, a hot tub, and an arcade/game room. Other amenities at this family-friendly villa include laundry facilities, barbecue grills, and a garden.
Pool
Hot Tub
Family Retreat with Autumn Views and Game Room

Family Retreat with Autumn Views and Game Room

3 out of 5
Stony Point NY
Guests of this villa enjoy features like a gym, a hot tub, and an arcade/game room. Other amenities at this family-friendly villa include laundry facilities, a garden, and barbecue grills.
Pool
Hot Tub
Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard

Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard

Chester NY
Guests of this villa enjoy features like an outdoor pool, a gym, and an arcade/game room. Other amenities at this family-friendly villa include laundry facilities and a garden.
Pool
Kitchen
Charming 3-bedroom villa with WiFi, AC in fabulous Monroe

Charming 3-bedroom villa with WiFi, AC in fabulous Monroe

Monroe NY
At this villa, guests have access to features like laundry facilities. This smoke-free villa also has a garden.
Kitchen
Washer
Don't see what you're looking for?
See all available properties in New Windsor
View all properties
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.

Hotel Options in New Windsor

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

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

    915 Union Ave New Windsor NY
    $96 nightly
    The price is $109 total per night from Mar 3 to Mar 4
    $109 total
    Mar 3 - Mar 4
    Total with taxes and fees
    8.4/10 Very Good! (1,003 reviews)
    Homewood Suites Stewart Airport

    Homewood Suites Stewart Airport

    180 Breunig Rd New Windsor NY
    $130 nightly
    The price is $147 total per night from Mar 15 to Mar 16
    $147 total
    Mar 15 - Mar 16
    Total with taxes and fees
    9.2/10 Wonderful! (1,001 reviews)
    Courtyard by Marriott Poughkeepsie

    Courtyard by Marriott Poughkeepsie

    2641 South Road/Route 9 Poughkeepsie NY
    $105 nightly
    The price is $119 total per night from Mar 19 to Mar 20
    $119 total
    Mar 19 - Mar 20
    Total with taxes and fees
    8.8/10 Excellent! (1,000 reviews)

Luxury Villas

Book luxury villas in New Windsor
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in New Windsor. Villas, with their thoughtful layout and elegant décor, let you travel in style. They come in a variety of sizes and offer a great experience, whether you’re traveling on your own or with a group of friends. Orbitz has fantastic deals on villas in New Windsor, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in New Windsor
You won’t have a problem finding your own space in New Windsor. If you’re traveling in a group, go for a three-bedroom or larger villa; separate bedrooms can make it that much easier to keep the peace, especially when you’re all staying in one house. You can also explore New Windsor on your own and use a one-bedroom villa as your home base.

A top-end villa experience in New Windsor rivals that of a luxury resort. Float in a swimming pool with an elaborate mosaic bottom, work out in your own gym, and let the daily housekeeping staff clean up after you while a private chef whips up one delicious meal after another. This is the life!

New Windsor Villas essential information

Accommodation
27 Villas
Lowest Price
$109
Highest Price
$147
Popular accommodation
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space, Luxury 10BR Escape w/ Pool, Hot Tub & Game Lounge, Warm Escape, Wood Stove, HotTub, Pets, <1 Hr NYC, The Scenic Mansion With Breathtaking View, Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY., Grand 9BR Retreat w/Pool & Hot Tub, Family Retreat with Autumn Views and Game Room, Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard, Charming 3-bedroom villa with WiFi, AC in fabulous Monroe