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Search results; Over 1,000 homes in Highland

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Rooms in Highland
Inn at Twaalfskill - Room 2
3 bedrooms, 4 beds, 1 private bathroom
16–21 Sept
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5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Home in Highland
VIEWS on Hudson River / Luxury Modern Home
4 bedrooms, 5 beds, 3 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 10 reviews
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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, 78 reviews
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Guest favourite
Flat in Highland
View on Vineyard.
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.94 out of 5 average rating, 18 reviews
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Guest favourite
Home in Highland
Splendid Isolation @ Extraordinary Country Retreat
4 bedrooms, 4 beds, 5 bathrooms
17–22 Sept
4.98 out of 5 average rating, 80 reviews
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Home in Highland
Cliffside Luxury: Hot Tub, Sun & River Views!
3 bedrooms, 5 beds, 2.5 bathrooms
20–25 Sept
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
20–25 Sept
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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Guest favourite
Home in Highland
Modern Stylish Farmhouse
2 bedrooms, 3 beds, 1 bathroom
16–21 Sept
5.0 out of 5 average rating, 24 reviews
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Top guest favourite
Home in New Paltz
1875 School House near HV Rail Trail
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 94 reviews
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Home in New Paltz
Streamside Haven - Scenic and Walkable to Downtown
3 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.98 out of 5 average rating, 47 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, 397 reviews
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Home in New Paltz
Spa & Nature Retreat - New Paltz
3 bedrooms, 6 beds, 2 bathrooms
16–21 Sept
New place to stay
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Holiday home in Highland
Charming Vacation House w/ Pool & HotTub
3 bedrooms, 6 beds, 2.5 bathrooms
16–21 Sept
5.0 out of 5 average rating, 39 reviews
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Home in Milton
Historic 4BR Family Home Near Buttermilk Falls
4 bedrooms, 4 queen beds, 2 bathrooms
27 Sept – 2 Oct
4.75 out of 5 average rating, 237 reviews
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Home in Highland
Hudson Valley Estate 90 min from NYC Pool&GameRoom
4 bedrooms, 6 beds, 2.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 53 reviews
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Home in Clintondale
The Great Escape
5 bedrooms, 5 beds, 3 bathrooms
17–22 Sept
4.84 out of 5 average rating, 19 reviews
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Home in Highland
Bedelle Farmhouse on the Farm
3 bedrooms, 4 beds, 1.5 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 28 reviews
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Top guest favourite
Home in Highland
Stone House - 4 bdrm, for 10 guests
4 bedrooms, 6 beds, 3 bathrooms
22–27 Sept
5.0 out of 5 average rating, 11 reviews