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Search results; Over 1,000 homes in New Windsor

Top guest favourite
Home in New Windsor
View House
1 bedroom, 1 bed, 1 shared bathroom
16–21 Oct
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4.92 out of 5 average rating, 156 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
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, 41 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
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
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
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
Flat in Montgomery
Montgomery Village King Bed 2BR/2B Ground Floor
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Home in Cold Spring
Charming Home in Cold Spring, NY
4 bedrooms, 4 beds, 3 bathrooms
9–14 Sept
4.98 out of 5 average rating, 59 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
Top guest favourite
Tiny home in Wallkill
Get Away to "Hygge" Tiny House on 75 Private Acres
1 queen bed, 1 bathroom
16–21 Sept
4.99 out of 5 average rating, 378 reviews
Top guest favourite
Flat in Newburgh
Sunny Boho Escape | Deck & River Views
2 bedrooms, 2 queen beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 68 reviews
Top guest favourite
Room in Beacon
Steps away from nature!
1 bed, 1 bathroom
14–19 Sept
4.94 out of 5 average rating, 254 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
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
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 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