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Search results; Over 1,000 homes in Highland

Guest favourite
Cottage in Highland
Little Yellow Cottage New Paltz - Kitchen wash/dry
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
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4.89 out of 5 average rating, 708 reviews
Top guest favourite
Home in Highland
VIEWS on Hudson River / Luxury Modern Home
4 bedrooms, 5 beds, 3 bathrooms
18–23 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Guest suite in Highland
Cozy Studio | Near World’s Longest Walkway Bridge
1 bedroom, 3 beds, 1 bathroom
28 Aug – 2 Sept
4.94 out of 5 average rating, 70 reviews
Guest favourite
Flat in Highland
View on Vineyard.
1 bedroom, 1 queen bed, 1 bathroom
25–30 Oct
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Home in Highland
Cliffside Luxury: Hot Tub, Sun & River Views!
3 bedrooms, 5 beds, 2.5 bathrooms
14–19 Aug
5.0 out of 5 average rating, 11 reviews
Superhost
Home in Highland
Peaceful Spacious 5 BR Family Home with a View
5 bedrooms, 7 beds, 4 bathrooms
16–21 Aug
New place to stay
Guest favourite
Home in Highland
Modern Stylish Farmhouse
2 bedrooms, 3 beds, 1 bathroom
18–23 Aug
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Farm stay in High Falls
Dave's Milk Barn
2 bedrooms, 2 beds, 1 bathroom
4–9 Oct
4.88 out of 5 average rating, 1083 reviews
Guest favourite
Tent in High Falls
Stargazer Glamping Tent at Clove Valley Farm
1 bedroom, 1 double bed, No bathroom
23–28 Aug
4.9 out of 5 average rating, 112 reviews
Guest favourite
Home in Highland
Splendid Isolation @ Extraordinary Country Retreat
4 bedrooms, 4 beds, 5 bathrooms
7–14 Sept
4.97 out of 5 average rating, 79 reviews
Top guest favourite
Room in Rhinecliff
Rhinecliff: King Room with Balcony
1 king bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 15 reviews
Home in Highland
7 Mi to The Walkway: Hudson Valley Adventure Base
4 bedrooms, 7 beds, 1.5 bathrooms
7–12 Sept
4.83 out of 5 average rating, 6 reviews
Top guest favourite
Room in New Paltz
Nature Secluded Room 5min to town, 12 to mountains
1 queen bed, 1 bathroom
16–21 Aug
4.99 out of 5 average rating, 204 reviews
Guest suite in Poughkeepsie
Cedar Grove
1 bedroom, 1 queen bed, 1 bathroom
1–6 Sept
New place to stay
Guest favourite
Tiny home in Marlboro
Orchard Views from a Light-Filled Tiny Home with a Fire Pit
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
4.96 out of 5 average rating, 365 reviews
Top guest favourite
Home in Kingston
Hillside Views in Hudson Valley
1 bedroom, 1 queen bed, 1 bathroom
14–19 Nov
4.97 out of 5 average rating, 194 reviews
Home in Highland
Secluded House on 55 ac w/pool 5 Mins to New Paltz
3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
New place to stay
Guest favourite
Camper van/Motorhome in New Paltz
Daisy - 2025 Airstream Under the Gunks
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
4.94 out of 5 average rating, 17 reviews
Top guest favourite
Home in Kingston
Hudson Valley Hygge House~ comfort in the country!
2 bedrooms, 2 beds, 2.5 bathrooms
20–25 Sept
4.95 out of 5 average rating, 366 reviews