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

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.
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 |
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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. |
More accommodations in New Windsor
Top trending hotels in New Windsor

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

Homewood Suites Stewart Airport

HYATT house Fishkill/Poughkeepsie

Overlook Lodge at Bear Mountain
More ways to explore New Windsor
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^Subject to availability and chosen travel dates.