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Search results; Over 1,000 homes in New Windsor

Top guest favourite
Home in New Windsor
2-Queen 1-Twin 2-Bath Home West Point/Low-Hud Area
3 bedrooms, 6 beds, 2 private bathrooms
21–26 Oct
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4.93 out of 5 average rating, 71 reviews
Guest favourite
Home in New Windsor
4 Bd Paradise Gorgeous Design Close to All!
4 bedrooms, 4 beds, 2 bathrooms
31 Oct – 5 Nov
4.96 out of 5 average rating, 151 reviews
Top guest favourite
Guest suite in New Windsor
A Cozy-Luxe Getaway | Scenic & Serene
1 bedroom, 1 queen bed, 1 bathroom
11–16 Oct
4.93 out of 5 average rating, 42 reviews
Room in New Windsor
Spacious & Cozy Private Suite Near West Point
1 queen bed, 1 bathroom
11–16 Sept
New place to stay
Guest favourite
Room in New Windsor
Hudson Valley Historic, Green Room
1 double bed, 1 bathroom
19–24 Sept
4.88 out of 5 average rating, 294 reviews
Top guest favourite
Room in New Windsor
Hudson Valley Historic, Rose Room
1 single bed, 1 bathroom
13–18 Sept
4.93 out of 5 average rating, 297 reviews
Home in Montgomery
Cozy Montgomery Home
2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Dec
New place to stay
Home in Montgomery
Walk to Village! 5BR Home, 2 Kitchens, King Beds
6 bedrooms, 8 beds, 4.5 bathrooms
13–18 Sept
Guest favourite
Home in Fishkill Village
Hudson Valley Suite Home Cinema, Fireplace, Gazebo
3 bedrooms, 4 beds, 2 bathrooms
11–16 Nov
4.82 out of 5 average rating, 28 reviews
Top guest favourite
Home in Newburgh
The Chrisearl
4 bedrooms, 4 beds, 1 bathroom
18–23 Oct
4.9 out of 5 average rating, 48 reviews
Top guest favourite
Home in Cold Spring
Charming Home in Cold Spring, NY
4 bedrooms, 4 beds, 3 bathrooms
10–15 Sept
4.98 out of 5 average rating, 59 reviews
Guest favourite
Home in New Windsor
Charming Farmhouse 13mi to West Point!
3 bedrooms, 7 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Townhouse in Beacon
Pet-Friendly 3BR Retreat – Walk to Shops & Cafe
3 bedrooms, 3 beds, 1.5 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 389 reviews
Guest favourite
Home in New Windsor
Hudson Valley Hideaway
4 bedrooms, 5 beds, 2.5 bathrooms
10–15 Nov
4.93 out of 5 average rating, 55 reviews
Superhost
Home in Newburgh
Hot Tub Bliss on 2 acres 16mi to West Point
3 bedrooms, 6 beds, 2 bathrooms
13–18 Sept
4.92 out of 5 average rating, 212 reviews
Top guest favourite
Home in Cornwall
Sunset House: near West Point, Hiking & Woodbury
3 bedrooms, 3 beds, 2 bathrooms
14–19 Sept
4.98 out of 5 average rating, 58 reviews
Top guest favourite
Home in Newburgh
Balmville Mid-Century Gem & Work From Home Retreat
3 bedrooms, 4 beds, 2 bathrooms
9–14 Nov
4.99 out of 5 average rating, 210 reviews
Top guest favourite
Home in Beacon
River & Mountain Views | Hot Tub | Arcade | Bar
5 bedrooms, 8 beds, 3.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Farm stay in Goshen
Bright Farm House- Tranquil setting
3 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
4.89 out of 5 average rating, 417 reviews