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Search results; Over 1,000 homes in New Windsor

Top guest favourite
Guest suite in New Windsor
A Cozy-Luxe Getaway | Scenic & Serene
1 bedroom, 1 bed, 1 private bathroom
27 Oct – 1 Nov
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4.93 out of 5 average rating, 42 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
Home in Newburgh
The Chrisearl
4 bedrooms, 4 beds, 1 bathroom
18–23 Oct
4.9 out of 5 average rating, 49 reviews
Guest favourite
Room in New Windsor
Hudson Valley Historic, Rose Room
1 single bed, 1 bathroom
26 Sept – 1 Oct
4.92 out of 5 average rating, 298 reviews
Home in Montgomery
Walk to Village! 5BR Home, 2 Kitchens, King Beds
6 bedrooms, 8 beds, 4.5 bathrooms
22–27 Oct
Guest favourite
Home in Fishkill Village
Hudson Valley Suite Home Cinema, Fireplace, Gazebo
3 bedrooms, 4 beds, 2 bathrooms
5–10 Dec
4.82 out of 5 average rating, 28 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
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
Guest favourite
Room in New Windsor
Hudson Valley Historic, Green Room
1 double bed, 1 bathroom
20–25 Sept
4.88 out of 5 average rating, 294 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
Guest favourite
Home in New Windsor
2-Queen 1-Twin 2-Bath Home West Point/Low-Hud Area
3 bedrooms, 6 beds, 2 bathrooms
12–17 Nov
4.93 out of 5 average rating, 71 reviews
Home in Monroe
Spacious 4BR Retreat | Legoland • Warwick • Trails
5 bedrooms, 7 beds, 2 bathrooms
21–26 Oct
New place to stay
Guest favourite
Home in New Windsor
Charming Farmhouse 13mi to West Point!
3 bedrooms, 7 beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 26 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
Room in New Windsor
Spacious & Cozy Private Suite Near West Point
1 queen bed, 1 bathroom
4–9 Jan
New place to stay
Guest favourite
Home in Cornwall-on-Hudson
Cozy Riverfront Victorian in the Hudson Valley
6 bedrooms, 6 beds, 2 bathrooms
20–25 Sept
4.93 out of 5 average rating, 193 reviews
Superhost
Home in Newburgh
Hot Tub Bliss on 2 acres 16mi to West Point
3 bedrooms, 6 beds, 2 bathrooms
20–25 Sept
4.92 out of 5 average rating, 212 reviews
Top guest favourite
Flat in Montgomery
Montgomery Village King Bed 2BR/2B Ground Floor
2 bedrooms, 3 beds, 2 bathrooms
11–16 Oct
4.93 out of 5 average rating, 14 reviews