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Search results; Over 1,000 homes in New Windsor

Cottage in New Windsor
Lake Front Property Sauna and Pool Near West Point
3 bedrooms, 3 beds, 2.5 private bathrooms
13–18 Jul
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4.56 out of 5 average rating, 229 reviews
Tiny home in Rock Tavern
Enchanted Woodland Tiny Home Retreat
1 bedroom, 1 queen bed, 1 bathroom
12–17 Jul
New place to stay
Guest favourite
Room in New Windsor
Hudson Valley Historic, Botanical Room
1 queen bed, 1 bathroom
5–10 Jul
4.88 out of 5 average rating, 129 reviews
Guest favourite
Tiny home in Newburgh
Cabin in the Heart of the Hudson Valley, Cabin 1
1 bedroom, 1 queen bed, 1 bathroom
5–10 Jul
4.94 out of 5 average rating, 233 reviews
Guest favourite
Flat in Newburgh
Special Nest w Private Entrance River View Porches
1 bedroom, 1 queen bed, 2 bathrooms
26–31 Aug
4.89 out of 5 average rating, 261 reviews
Top guest favourite
Barn in Montgomery
16taft
2 beds, 1 bathroom
5–10 Jul
4.97 out of 5 average rating, 39 reviews
Top guest favourite
Guest suite in New Windsor
Spacious Studio/ SKAC/USMA/Morning Muffins
1 bedroom, 2 queen beds, 1 bathroom
12–17 Jul
4.96 out of 5 average rating, 283 reviews
Home in Montgomery
Treehouse-Inspired Cabin Escape w/ Theatre & Gym
3 bedrooms, 4 beds, 3.5 bathrooms
27 Oct – 1 Nov
Top guest favourite
Flat in Newburgh
Sunny Boho Escape | Deck & River Views
2 bedrooms, 2 queen beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 64 reviews
Top guest favourite
Home in Marlboro
Hudson Valley Farmhouse | Winery & Hiking Getaway
3 bedrooms, 4 beds, 2.5 bathrooms
12–17 Jul
4.99 out of 5 average rating, 225 reviews
Top guest favourite
Home in Montgomery
Luxe 3BR 2.5 bath King Beds in Montgomery Village
3 bedrooms, 3 king beds, 2.5 bathrooms
13–18 Jul
5.0 out of 5 average rating, 17 reviews
Home in New Windsor
Storm King Lodge
4 bedrooms, 5 beds, 4 bathrooms
11–16 Jul
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Newburgh
Hot Tub Bliss on 2 acres 16mi to West Point
3 bedrooms, 6 beds, 2 bathrooms
1–6 Jul
4.92 out of 5 average rating, 199 reviews
Top guest favourite
Cottage in Cornwall-on-Hudson
Historic 1800s Cornwall-On-Hudson Cottage!
2 bedrooms, 3 beds, 2 bathrooms
17–22 Jul
5.0 out of 5 average rating, 81 reviews
Top guest favourite
Place to stay in Warwick
Luxe Penthouse Studio MainSt Warwick, SteamShower!
1 bedroom, 1 king bed, 1 bathroom
6–11 Jul
4.96 out of 5 average rating, 371 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 Sept
4.94 out of 5 average rating, 64 reviews
Top guest favourite
Cottage in Montgomery
The Pullman Cottage NYC Escape • Dogs Stay Free
2 bedrooms, 2 queen beds, 1 bathroom
16–21 Jul
5.0 out of 5 average rating, 80 reviews
Guest favourite
Bed and breakfast in Middletown
Charming Upstate New York Inn Cozy Suite #3
1 bedroom, 2 beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in New Windsor
Farmhouse w/ Pool, Sauna & Hot Tub near Storm King
4 bedrooms, 4 beds, 2.5 bathrooms
26–31 Jul
5.0 out of 5 average rating, 94 reviews