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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
11–16 Oct
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4.93 out of 5 average rating, 41 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
Room in New Windsor
Hudson Valley Historic, Rose Room
1 single bed, 1 bathroom
6–11 Sept
4.93 out of 5 average rating, 297 reviews
Top guest favourite
Home in New Windsor
2-Queen 1-Twin 2-Bath Home West Point/Low-Hud Area
3 bedrooms, 6 beds, 2 bathrooms
21–26 Oct
4.94 out of 5 average rating, 70 reviews
Guest favourite
Room in New Windsor
Hudson Valley Historic, Green Room
1 double bed, 1 bathroom
7–12 Sept
4.88 out of 5 average rating, 293 reviews
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 New Windsor
Storm King Lodge
4 bedrooms, 5 beds, 4 bathrooms
7–12 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Townhouse in Beacon
Pet-Friendly 3BR Retreat – Walk to Shops & Cafe
3 bedrooms, 3 beds, 1.5 bathrooms
13–18 Sept
4.96 out of 5 average rating, 389 reviews
Guest favourite
Home in Newburgh
The Chrisearl
4 bedrooms, 4 beds, 1 bathroom
18–23 Oct
4.89 out of 5 average rating, 47 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, 54 reviews
Top guest favourite
Guest suite in Rock Tavern
Beneath the Bark: A peaceful, scenic getaway
1 bedroom, 2 beds, 1 bathroom
13–18 Nov
5.0 out of 5 average rating, 21 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, 15 reviews
Top guest favourite
Home in Monroe
Lakeview group stay near wedding venues
7 bedrooms, 10 beds, 4 bathrooms
5–10 Sept
4.96 out of 5 average rating, 52 reviews
Guest favourite
Home in Newburgh
The Overlook 350- Where Family and Friends Retreat
4 bedrooms, 4 beds, 1.5 bathrooms
14–19 Sept
4.96 out of 5 average rating, 55 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
Guest suite in Newburgh
Salvick House, Central to all Bethels
2 bedrooms, 3 beds, 1 bathroom
11–16 Oct
4.98 out of 5 average rating, 223 reviews
Top guest favourite
Home in Beacon
Designer-Restored Victorian • Walk to Train & Main
2 bedrooms, 3 beds, 1.5 bathrooms
30 Oct – 4 Nov
4.99 out of 5 average rating, 89 reviews
Top guest favourite
Cottage in Goshen
Cheery & Peaceful Farm Cottage, 10 Min to LEGOLAND
2 bedrooms, 2 beds, 1 bathroom
4–9 Nov
4.92 out of 5 average rating, 347 reviews
Guest favourite
Home in New Windsor
Charming Farmhouse 13mi to West Point!
3 bedrooms, 7 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 26 reviews