Book Holiday Homes in New Windsor

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Featured Holiday Homes in New Windsor

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
Located in Carmel, this vacation home is in the mountains, a 4-minute drive from Clarence Fahnestock State Park and 8 minutes from Chuang Yen Monastery.
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Bright Cornwall-On-Hudson Vacation Rental!

Bright Cornwall-On-Hudson Vacation Rental!

Cornwall-On-Hudson
With a stay at this vacation home in Cornwall, you'll be in the mountains, within a 10-minute drive of United States Military Academy and New York Military ...
Bright Cornwall-On-Hudson Vacation Rental!
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits

Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits

Cold Spring
When you stay at this vacation home in Cold Spring, you'll be on a river, within a 5-minute drive of Clarence Fahnestock State Park and Hudson Highlands State ...
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
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Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

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

Stony Point
Located in Stony Point, this vacation home is within a 15-minute drive of Bear Mountain State Park and United States Military Academy.
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
Renovated 1850's Cottage on Storm King Mountain

Renovated 1850's Cottage on Storm King Mountain

Cornwall-on-Hudson
With a stay at this vacation home in Cornwall, you'll be within a 5-minute drive of United States Military Academy and Storm King State Park.
Renovated 1850's Cottage on Storm King Mountain
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

Hopewell Junction
Located in Hopewell Junction, this vacation home is in the mountains, within a 10-minute drive of Clarence Fahnestock State Park and Hudson Valley Research ...
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz

Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz

Highland
When you stay at this vacation home in Highland, you'll be on a river, within a 15-minute drive of Vassar College and Culinary Institute of America.
Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz
CREATIVES DREAM GETAWAY

CREATIVES DREAM GETAWAY

Gardiner
With a stay at this vacation home in Gardiner, you'll be in the mountains, within a 10-minute drive of Minnewaska State Park and DM Weil Gallery.
CREATIVES DREAM GETAWAY
Pet-Friendly ‘Pond View Loft' w/ Private Pool!

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

Pine Bush
With a stay at this vacation home in Pine Bush, you'll be on a river, within a 15-minute drive of Minnewaska State Park and Brimstone Hill Winery.
Pet-Friendly ‘Pond View Loft' w/ Private Pool!
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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
350 Holiday Homes
Lowest Price
AU$203
Highest Price
AU$275
Popular accommodation
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn. , Bright Cornwall-On-Hudson Vacation Rental!, Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits, Updated Getaway w/ Pool & Hot Tub on < 3 Acres!, Renovated 1850's Cottage on Storm King Mountain, 1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views, Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz, CREATIVES DREAM GETAWAY, Pet-Friendly ‘Pond View Loft' w/ Private Pool!

Top trending hotels in New Windsor

Red Roof Inn & Suites Newburgh – Stewart Airport

Red Roof Inn & Suites Newburgh – Stewart Airport

2 out of 5
915 Union Ave, New Windsor, NY
Fully refundableReserve now, pay when you stay
The price is AU$203 per night from 23 Jun to 24 Jun
AU$203
per night
23 Jun - 24 Jun
Located in New Windsor, Red Roof Inn & Suites Newburgh – Stewart Airport is within a 5-minute drive of Hamilton Fish Bridge and Orange County Choppers.
Red Roof Inn & Suites Newburgh – Stewart Airport
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 AU$275 per night from 7 Jul to 8 Jul
AU$275
per night
7 Jul - 8 Jul
With a stay at Homewood Suites Stewart Airport in New Windsor, you'll be within a 5-minute drive of National Purple Heart Hall of Honor and Hamilton Fish ...
Homewood Suites Stewart Airport
HYATT house Fishkill/Poughkeepsie

HYATT house Fishkill/Poughkeepsie

3 out of 5
100 Westage Business Center Dr., Fishkill, NY
Fully refundable
The price is AU$227 per night from 16 Jun to 17 Jun
AU$227
per night
16 Jun - 17 Jun
Located in Fishkill, HYATT house Fishkill/Poughkeepsie is a 4-minute drive from SplashDown Beach and 10 minutes from Dia Beacon.
HYATT house Fishkill/Poughkeepsie
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DoubleTree by Hilton Poughkeepsie

DoubleTree by Hilton Poughkeepsie

4 out of 5
40 Civic Center Plz, Poughkeepsie, NY
Fully refundableReserve now, pay when you stay
The price is AU$216 per night from 27 Jun to 28 Jun
AU$216
per night
27 Jun - 28 Jun
With a stay at DoubleTree by Hilton Poughkeepsie, you'll be centrally located in Poughkeepsie, within a 5-minute drive of Marist College and Vassar College.
DoubleTree by Hilton Poughkeepsie
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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.