Book Holiday Homes in New Windsor

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Featured Holiday Homes in New Windsor

Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

New Windsor
Book a stay at this family-friendly vacation home in New Windsor. Enjoy free WiFi, a garden, and patios. Our guests praise the bathrooms in our reviews. Popular ...
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
The Perfect up to date Private Getaway to call home for a while

The Perfect up to date Private Getaway to call home for a while

Bloomingburg
Stay at this vacation home in Bloomingburg. Enjoy free WiFi, a garden, and patios. Popular attractions Mamakating Town Park and Veteran's Memorial Park are located ...
The Perfect up to date Private Getaway to call home for a while
Cozy House 3 Blocks From West Pt

Cozy House 3 Blocks From West Pt

Highland Falls
Stay at this vacation home in Highland Falls. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions West Point Museum and Christl Arena are ...
Cozy House 3 Blocks From West Pt
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 Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!

Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!

wallkill
The price is NZ$635 per night from 1 Jan to 2 Jan
NZ$635
includes taxes & fees
1 Jan - 2 Jan 2025
Book a stay at this family-friendly vacation home in Wallkill. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Angry Orchard and Tuthilltown ...
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park

Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park

Pine Bush
Book a stay at this family-friendly vacation home in Pine Bush. Enjoy free WiFi, a garden, and patios. Popular attractions Brimstone Hill Winery and Ellenville ...
Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park
Pet-Friendly ‘Pond View Loft' w/ Private Pool!

Pet-Friendly ‘Pond View Loft' w/ Private Pool!

Pine Bush
Stay at this vacation home in Pine Bush. Enjoy private pools, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Brimstone Hill Winery ...
Pet-Friendly ‘Pond View Loft' w/ Private Pool!
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Carmel Hamlet
Stay at this vacation home in Carmel. Enjoy free WiFi, a garden, and patios. Our guests praise the property condition in our reviews. Popular attractions Chuang ...
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Dream escape, new modern farmhouse, stunning views, game room & hot tub for 14+!

Dream escape, new modern farmhouse, stunning views, game room & hot tub for 14+!

Montgomery
Book a stay at this family-friendly vacation home in Montgomery. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Popular attractions City Winery ...
Dream escape, new modern farmhouse, stunning views, game room & hot tub for 14+!
Spectacular ~10k sqft Mansion w/Pool&Tennis

Spectacular ~10k sqft Mansion w/Pool&Tennis

Goshen
The price is NZ$5,255 per night from 25 Dec to 26 Dec
NZ$5,255
includes taxes & fees
25 Dec - 26 Dec
Book a stay at this family-friendly vacation home in Goshen. Enjoy free WiFi, private pools, and a water park. Popular attractions LEGOLAND® New York and Castle ...
Spectacular ~10k sqft Mansion w/Pool&Tennis
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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
356 Holiday Homes
Lowest Price
NZ$182
Highest Price
NZ$5,255
Popular accommodation
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel. , The Perfect up to date Private Getaway to call home for a while, Cozy House 3 Blocks From West Pt, Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!, Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park, Pet-Friendly ‘Pond View Loft' w/ Private Pool!, Privacy in the hills one hour from NYC and minutes to Breakneck Mtn. , Dream escape, new modern farmhouse, stunning views, game room & hot tub for 14+!, Spectacular ~10k sqft Mansion w/Pool&Tennis

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$206 per night from 1 Jan to 2 Jan
NZ$206
includes taxes & fees
1 Jan - 2 Jan 2025
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$266 per night from 25 Dec to 26 Dec
NZ$266
includes taxes & fees
25 Dec - 26 Dec
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
Best Western Fishkill Inn & Suites

Best Western Fishkill Inn & Suites

3.5 out of 5
14 Schuyler Blvd, Fishkill, NY
Fully refundableReserve now, pay when you stay
The price is NZ$182 per night from 1 Jan to 2 Jan
NZ$182
includes taxes & fees
1 Jan - 2 Jan 2025
Book a stay at this business-friendly hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Best Western Fishkill Inn & Suites
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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$235 per night from 21 Dec to 22 Dec
NZ$235
includes taxes & fees
21 Dec - 22 Dec
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
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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.