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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
4–9 Oct
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4.89 out of 5 average rating, 707 reviews
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
Home in Highland
Two Tillson
2 bedrooms, 2 queen beds, 2.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 18 reviews
Guest favourite
Flat in Highland
View on Vineyard.
1 bedroom, 1 queen bed, 1 bathroom
6–11 Sept
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Guest suite in Highland
Cozy Studio | Near World’s Longest Walkway Bridge
1 bedroom, 3 beds, 1 bathroom
31 Aug – 5 Sept
4.94 out of 5 average rating, 70 reviews
Top guest favourite
Home in Highland
Cliffside Luxury: Hot Tub, Sun & River Views!
3 bedrooms, 5 beds, 2.5 bathrooms
10–15 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
Room in Poughkeepsie
Walk to Marist | Cozy Private Room
1 double bed, 1 bathroom
20–25 Dec
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Farm stay in High Falls
Dave's Milk Barn
2 bedrooms, 2 beds, 1 bathroom
2–7 Nov
4.88 out of 5 average rating, 1082 reviews
Guest favourite
Home in Highland
Modern Stylish Farmhouse
2 bedrooms, 3 beds, 1 bathroom
11–16 Aug
5.0 out of 5 average rating, 23 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
Guest favourite
Guest suite in Highland
Peaceful Home (full kitchen, washer/dryer)
1 bedroom, 4 beds, 1 bathroom
7–12 Sept
4.87 out of 5 average rating, 358 reviews
Top guest favourite
Room in Poughkeepsie
Hudson Pond · Garden Queen Suite · GF Breakfast
1 queen bed, 1 bathroom
31 Aug – 6 Sept
4.99 out of 5 average rating, 164 reviews
Top guest favourite
Campsite in Accord
Canyon Edge off - grid Bungalow
1 queen bed, No bathroom
16–21 Aug
4.95 out of 5 average rating, 548 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
Top guest favourite
Home in Highland
Hudson Valley Estate 90 min from NYC Pool&GameRoom
4 bedrooms, 6 beds, 2.5 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 52 reviews
Guest favourite
Camper van/Motorhome in New Paltz
Daisy - 2025 Airstream Under the Gunks
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.93 out of 5 average rating, 14 reviews
Top guest favourite
Home in Staatsburg
Boulder Tree House
1 bedroom, 2 beds, 2 bathrooms
7–12 Nov
4.99 out of 5 average rating, 134 reviews
Guest favourite
Room in Poughkeepsie
Shared Youth Hostel coed space H2
1 single bed, 1 bathroom
16–21 Aug
4.83 out of 5 average rating, 42 reviews