Book Holiday Homes in New Windsor

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Featured Holiday Homes in New Windsor

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
The price is NZ$517 per night from 24 Mar to 25 Mar
NZ$517
includes taxes & fees
24 Mar - 25 Mar
Stay at this vacation home in Fishkill. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions SplashDown Beach and Van Wyck Homestead Museum ...
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Spacious New Luxurious holiday house in lovely Hudson Valley

Spacious New Luxurious holiday house in lovely Hudson Valley

Poughkeepsie
Stay at this vacation home in Poughkeepsie. Enjoy patios, in-room jetted tubs, and in-room fireplaces. Popular attractions Overlook Drive-In Theater and Richard ...
Spacious New Luxurious holiday house in lovely Hudson Valley
Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

Newburgh
Book a stay at this family-friendly vacation home in Newburgh. Enjoy free WiFi, a water park, and a fitness center. Our guests praise the helpful staff in our ...
Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View
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Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

Stony Point
Book a stay at this family-friendly vacation home in Stony Point. Enjoy private pools, a fitness center, and furnished patios. Popular attractions Marian Shrine ...
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
The Cozy Goshen Home, 5mins from LEGOLAND and near skiing!

The Cozy Goshen Home, 5mins from LEGOLAND and near skiing!

Goshen
Book a stay at this family-friendly vacation home in Goshen. Enjoy an in-room coffeemaker and air conditioning. Popular attractions LEGOLAND® New York and Castle ...
The Cozy Goshen Home, 5mins from LEGOLAND and near skiing!
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

2 out of 5
New Paltz
The price is NZ$686 per night from 24 Mar to 25 Mar
NZ$686
includes taxes & fees
24 Mar - 25 Mar
Stay at this vacation home in New Paltz. Enjoy free WiFi, a garden, and patios. Popular attractions Testimonial Gateway and Loren Campbell Memorial Field are ...
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Renovated House w/Hot Tub, Deck, Grill & Fire Pit

Renovated House w/Hot Tub, Deck, Grill & Fire Pit

Goshen
The price is NZ$929 per night from 24 Mar to 25 Mar
NZ$929
includes taxes & fees
24 Mar - 25 Mar
Stay at this vacation home in Goshen. Enjoy free WiFi, a water park, and a garden. Popular attractions LEGOLAND® New York and Castle Fun Center are located ...
Renovated House w/Hot Tub, Deck, Grill & Fire Pit
Modern, Magical Woodsy Escape 1 Hour From NYC

Modern, Magical Woodsy Escape 1 Hour From NYC

Putnam Valley
Stay at this vacation home in Putnam Valley. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Donald J. Trump State Park and Jefferson Valley ...
Modern, Magical Woodsy Escape 1 Hour From NYC
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

Greenwood Lake
Stay at this vacation home in Greenwood Lake. Enjoy an in-room coffeemaker, in-room fireplaces, and air conditioning. Popular attractions World Headquarters ...
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.
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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.

New Windsor Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our New Windsor vacation homes are the perfect way for you to wing it.

Holiday houses in New Windsor let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of New Windsor in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local New Windsor adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in New Windsor with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of New Windsor vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

New Windsor Holiday Homes essential information

Accommodation
339 Holiday Homes
Lowest Price
NZ$196
Highest Price
NZ$929
Popular accommodation
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo, Spacious New Luxurious holiday house in lovely Hudson Valley, Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View, Updated Getaway w/ Pool & Hot Tub on < 3 Acres!, The Cozy Goshen Home, 5mins from LEGOLAND and near skiing!, Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks, Renovated House w/Hot Tub, Deck, Grill & Fire Pit, Modern, Magical Woodsy Escape 1 Hour From NYC, BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

Top trending hotels in New Windsor

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

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

2 out of 5
915 Union Ave, New Windsor, NY
Fully refundableReserve now, pay when you stay
The price is NZ$196 per night from 12 Mar to 13 Mar
NZ$196
includes taxes & fees
12 Mar - 13 Mar
Book a stay at this business-friendly hotel in New Windsor. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the ...
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Homewood Suites Stewart Airport

Homewood Suites Stewart Airport

3 out of 5
180 Breunig Rd, New Windsor, NY
Fully refundableReserve now, pay when you stay
The price is NZ$234 per night from 17 Mar to 18 Mar
NZ$234
includes taxes & fees
17 Mar - 18 Mar
Stay at this 3-star hotel in New Windsor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
Homewood Suites Stewart Airport
HYATT house Fishkill/Poughkeepsie

HYATT house Fishkill/Poughkeepsie

3 out of 5
100 Westage Business Center Dr., Fishkill, NY
Fully refundableReserve now, pay when you stay
The price is NZ$204 per night from 17 Mar to 18 Mar
NZ$204
includes taxes & fees
17 Mar - 18 Mar
Stay at this 3-star business-friendly hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
HYATT house Fishkill/Poughkeepsie
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Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive, Bear Mountain State Park, Bear Mountain, NY
Fully refundableReserve now, pay when you stay
The price is NZ$200 per night from 17 Mar to 18 Mar
NZ$200
includes taxes & fees
17 Mar - 18 Mar
Book a stay at this spa hotel in Bear Mountain. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
Overlook Lodge at Bear Mountain
Don't see what you're looking for?
See all available properties in New Windsor
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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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^Subject to availability and chosen travel dates.