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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
30 Aug – 4 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
21–26 Sept
4.96 out of 5 average rating, 48 reviews
Top guest favourite
Home in Philipstown
Modern, sun-filled farmhouse retreat
3 bedrooms, 3 queen beds
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
24–29 Aug
5.0 out of 5 average rating, 10 reviews
Guest favourite
Flat in Philipstown
Foxglove Farm
1 bedroom, 1 queen bed
18–23 Aug
4.9 out of 5 average rating, 276 reviews
Guest favourite
Chalet in Philipstown
Rare A-Frame in the Trees · 20 min to WP· 1 hr NYC
3 bedrooms
14–19 Sept
5.0 out of 5 average rating, 12 reviews
Guest favourite
Guest suite in Philipstown
House on the hill
2 bedrooms, 2 beds
26–31 Aug
4.83 out of 5 average rating, 72 reviews
Guest favourite
Home in Philipstown
Turtle Crossing - Garrison, NY
5 bedrooms, 6 beds
26–31 Aug
4.95 out of 5 average rating, 21 reviews
Top guest favourite
Cabin in Philipstown
Peaceful Mountain Cottage with a Sunset View
1 bedroom, 2 beds
20–25 Aug
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Philipstown
The Dugout • Cool Woodland Escape • 60 Min NYC
4 bedrooms, 4 beds
8–13 Sept
4.92 out of 5 average rating, 12 reviews
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Farm stay in Philipstown
Country Estate on Maple Syrup Farm, Tesla Charging
5 bedrooms, 5 beds
13–18 Sept
5.0 out of 5 average rating, 19 reviews
Guest favourite
Home in Philipstown
Serene Hilltop House - Garrison 5-BR w Heated Pool
5 bedrooms, 5 beds
8–13 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Tiny home in Cold Spring
Tiny house on tiny farm close to hiking trails.
1 bedroom, 1 double bed
30 Aug – 4 Sept
5.0 out of 5 average rating, 329 reviews
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Home in Philipstown
Gloves Off Retreat • A Quiet Hudson Valley Escape
3 bedrooms, 3 beds
27 Aug – 1 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Putnam Valley
Luxury Lake House Sauna 1h From NYC
2 bedrooms, 3 beds
5–10 Sept
4.99 out of 5 average rating, 186 reviews
Top guest favourite
Cabin in Fishkill Village
Secluded Hilltop Cabin near Beacon & Cold Spring
1 bedroom, 3 beds
14–19 Sept
4.97 out of 5 average rating, 147 reviews
Top guest favourite
Room in Beacon
Steps away from nature!
1 bed
19–24 Sept
4.94 out of 5 average rating, 247 reviews
Home in Philipstown
'The Glabin’: Garrison Gem w/ Hot Tub & Fire Pit
3 bedrooms, 3 beds
26–31 Aug
4.82 out of 5 average rating, 34 reviews
Guest favourite
Home in Putnam Valley
Serene Lakefront Getaway w/ Private Sauna
3 bedrooms, 3 beds
19–24 Sept
5.0 out of 5 average rating, 5 reviews