Over 1,000 places in Doodletown

Home in Fort Montgomery
West Point Cottage
May 6 – 11
New place to stay
Superhost
Home in Highland Falls
Discover Nature’s Glory! Perfect Family Home
5 beds
Apr 19 – 24
4.94 out of 5 average rating, 47 reviews
Superhost
Home in Tomkins Cove
Charming Hudson Valley 3-Bedroom Family Getaway
3 queen beds
Apr 27 – May 2
4.71 out of 5 average rating, 85 reviews
Guest favorite
Home in Highland Falls
Bear Mountain, Westpoint, & Hikers Retreat
4 beds
Apr 22 – 27
4.97 out of 5 average rating, 70 reviews
Guest favorite
Apartment in Highland Falls
Cozy 1-bedroom retreat minutes from West Point!
2 beds
Apr 28 – May 3
4.84 out of 5 average rating, 98 reviews
Guest favorite
Cottage in Cortlandt
The Little Cottage in the Woods
Apr 30 – May 5
4.99 out of 5 average rating, 159 reviews
Guest favorite
Guest suite in Highland Falls
Modern place with private gated parking.
1 queen bed
Apr 28 – May 3
4.94 out of 5 average rating, 32 reviews
Guest favorite
Guest suite in Fort Montgomery
West Point - Mountain Top Suite
2 beds
Apr 30 – May 5
4.94 out of 5 average rating, 418 reviews
Home in Philipstown
Cozy Bungalow on Hudson River 9 Mi. to West Point
3 beds
May 11 – 16
4.68 out of 5 average rating, 111 reviews
Superhost
Apartment in Tomkins Cove
Private 1-Bedroom apt with 2 beds
1 single bed
Apr 21 – 26
4.89 out of 5 average rating, 19 reviews
Guest favorite
Guest suite in Fort Montgomery
West Point/Bear Mountain/Hudson Valley Getaway
3 beds
May 6 – 11
4.99 out of 5 average rating, 94 reviews
Guest favorite
Guesthouse in Peekskill
Peekskill Carriage House Downtown Studio
1 bed
May 5 – 10
4.94 out of 5 average rating, 206 reviews
Guest favorite
Bed and breakfast in Highland Falls
Riverview B&B 2 Miles to West Point
2 beds
May 6 – 11
4.99 out of 5 average rating, 139 reviews
Guest favorite
Home in Tomkins Cove
Hudson Valley Victorian with River Views
4 beds
Apr 22 – 27
4.94 out of 5 average rating, 136 reviews
Guest favorite
Farm stay in Fort Montgomery
Secluded mountain top horse property near W. Point
3 beds
May 5 – 10
4.94 out of 5 average rating, 198 reviews
Guest favorite
Home in Highland Falls
Spacious, bright 5 bedroom house near West Point
6 beds
Apr 20 – 25
4.99 out of 5 average rating, 141 reviews
Guest favorite
Farm stay in Fort Montgomery
Secluded overlook cottage near West Point
1 queen bed
Apr 28 – May 3
4.97 out of 5 average rating, 148 reviews
Guest favorite
Cottage in Putnam Valley
Beautiful Cottage in Hudson Valley w/Pool & Views
4 beds
Apr 28 – May 3
4.98 out of 5 average rating, 46 reviews