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Search results; Over 1,000 homes in Highland

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Guest favourite
Home in Highland
Hudson Escape W/ Hot Tub + Bridge View
3 bedrooms, 4 beds, 1.5 private bathrooms
25–30 Oct
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4.88 out of 5 average rating, 52 reviews
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Home in Highland
VIEWS on Hudson River / Luxury Modern Home
4 bedrooms, 5 beds, 3 bathrooms
1–6 Nov
5.0 out of 5 average rating, 10 reviews
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Home in Highland
Zen Peaks Retreat
4 bedrooms, 9 beds, 2.5 bathrooms
4–9 Oct
4.95 out of 5 average rating, 22 reviews
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Top guest favourite
Home in Highland
Two Tillson
2 bedrooms, 2 queen beds, 2.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 32 reviews
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Top guest favourite
Guest suite in Highland
Cozy Studio | Near World’s Longest Walkway Bridge
1 bedroom, 3 beds, 1 bathroom
25–30 Oct
4.94 out of 5 average rating, 79 reviews
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Guest favourite
Flat in Highland
View on Vineyard.
1 bedroom, 1 queen bed, 1 bathroom
25–30 Oct
4.94 out of 5 average rating, 18 reviews
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Top guest favourite
Home in Highland
Cliffside Luxury: Hot Tub, Sun & River Views!
3 bedrooms, 5 beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 13 reviews
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Home in Highland
Private 4BR Hudson Valley Escape Near New Paltz
4 bedrooms, 4 queen beds, 3 bathrooms
25–30 Oct
4.91 out of 5 average rating, 82 reviews
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Home in Highland
Spacious 4BD Country Gem - Fire Pit & Chill Vibes
4 bedrooms, 4 queen beds, 3.5 bathrooms
11–16 Oct
4.96 out of 5 average rating, 79 reviews
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Holiday home in Highland
Charming Vacation House w/ Pool & HotTub
3 bedrooms, 6 beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 39 reviews
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Guest favourite
Home in Highland
Splendid Isolation @ Extraordinary Country Retreat
4 bedrooms, 4 beds, 5 bathrooms
5–10 Oct
4.98 out of 5 average rating, 80 reviews
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Home in Poughkeepsie
Washington Wonder Big 4bd/2b
4 bedrooms, 5 beds, 2 bathrooms
31 Oct – 5 Nov
4.97 out of 5 average rating, 86 reviews
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Home in Highland
Hudson Valley Estate 90 min from NYC Pool&GameRoom
4 bedrooms, 6 beds, 2.5 bathrooms
26–31 Oct
5.0 out of 5 average rating, 53 reviews
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Home in New Paltz
1875 School House near HV Rail Trail
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
4.97 out of 5 average rating, 94 reviews
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Home in New Paltz
Historic 1768 Farmhouse, quiet, charming, spacious
4 bedrooms, 6 beds, 2 bathrooms
25–30 Oct
5.0 out of 5 average rating, 82 reviews
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Guest favourite
Home in Poughkeepsie
Beautiful, Fun, Spacious 5 Acre Family Retreat
3 bedrooms, 7 beds, 2.5 bathrooms
11–16 Oct
4.93 out of 5 average rating, 116 reviews
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Guest favourite
Home in Highland
Modern Stylish Farmhouse
2 bedrooms, 3 beds, 1 bathroom
11–16 Oct
5.0 out of 5 average rating, 25 reviews
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Guest favourite
Flat in Poughkeepsie
3 Bdrm. Near Hudson Valley Colleges & Attractions
3 bedrooms, 3 beds, 1 bathroom
8–13 Nov
4.93 out of 5 average rating, 398 reviews
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Home in Highland
Stone House - 4 bdrm, for 10 guests
4 bedrooms, 6 beds, 3 bathrooms
5–10 Oct
5.0 out of 5 average rating, 11 reviews