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Search results; Over 1,000 homes in Philipstown

Guest favourite
Cottage in Philipstown
Modern Country Cottage by Bear Mountain
1 bedroom, 2 beds, 1 private bathroom
28 Aug – 2 Sept
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4.97 out of 5 average rating, 225 reviews
Top guest favourite
Home in Philipstown
Arkadia House Mid-century retreat with pool & view
3 bedrooms, 3 beds, 2 bathrooms
21–26 Sept
4.96 out of 5 average rating, 46 reviews
Top guest favourite
Chalet in Philipstown
Rare A-Frame in the Trees · 20 min to WP· 1 hr NYC
3 bedrooms, 2 bathrooms
24–29 Aug
5.0 out of 5 average rating, 11 reviews
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Home in Philipstown
Modern, sun-filled farmhouse retreat
3 bedrooms, 3 queen beds, 2.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 27 reviews
Guest favourite
Guest house in Philipstown
Modern Hudson Valley Loft | West Views, 1hr NYC
1 bedroom, 2 beds, 1 bathroom
21–26 Aug
5.0 out of 5 average rating, 10 reviews
Guest favourite
Flat in Philipstown
Foxglove Farm
1 bedroom, 1 queen bed, 1 bathroom
24–29 Aug
4.9 out of 5 average rating, 276 reviews
Guest favourite
Home in Philipstown
Turtle Crossing - Garrison, NY
5 bedrooms, 6 beds, 4.5 bathrooms
26–31 Aug
4.95 out of 5 average rating, 21 reviews
Top guest favourite
Farm stay in Philipstown
Country Estate on Maple Syrup Farm, Tesla Charging
5 bedrooms, 5 beds, 4.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 19 reviews
Guest favourite
Guest suite in Philipstown
House on the hill
2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
4.83 out of 5 average rating, 71 reviews
Top guest favourite
Home in Philipstown
The Dugout • Cool Woodland Escape • 60 Min NYC
4 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
4.92 out of 5 average rating, 12 reviews
Guest favourite
Rooms in Cold Spring
Classic Early 20th Century Chic Cold Spring Home
2 bedrooms, 2 double beds, 1 bathroom
26–31 Oct
4.92 out of 5 average rating, 78 reviews
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Cabin in Philipstown
Peaceful Mountain Cottage with a Sunset View
1 bedroom, 2 beds, 2 bathrooms
20–25 Aug
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Cold Spring
Modern Woodland Retreat • Forest Light & Quietude
3 bedrooms, 3 beds, 3 bathrooms
5–10 Oct
5.0 out of 5 average rating, 37 reviews
Top guest favourite
Tiny home in Cold Spring
Tiny house on tiny farm close to hiking trails.
1 bedroom, 1 double bed, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 327 reviews
Guest favourite
Home in Philipstown
Serene Hilltop House - Garrison 5-BR w Heated Pool
5 bedrooms, 5 beds, 4 bathrooms
8–13 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Philipstown
Gloves Off Retreat • A Quiet Hudson Valley Escape
3 bedrooms, 3 beds, 2 bathrooms
27 Aug – 1 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Highland Falls
Riverview B&B 2 Miles to West Point
1 bedroom, 2 beds, 1 bathroom
28 Oct – 2 Nov
4.99 out of 5 average rating, 195 reviews
Top guest favourite
Room in Beacon
Steps away from nature!
1 bed, 1 bathroom
19–24 Sept
4.94 out of 5 average rating, 246 reviews
Top guest favourite
Home in Philipstown
3BR Hudson River house near Bear Mountain
3 bedrooms, 3 beds, 2 bathrooms
27 Aug – 1 Sept
5.0 out of 5 average rating, 18 reviews