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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
30 Aug – 4 Sept
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4.89 out of 5 average rating, 701 reviews
Superhost
Home in Highland
VIEWS on Hudson River / Luxury Modern Home
New place to stay, 4 bedrooms, 5 beds, 3 bathrooms
19–24 Jul
Top guest favourite
Guest suite in Highland
Cozy Studio | Near World’s Longest Walkway Bridge
4.94 out of 5 average rating, 65 reviews, 1 bedroom, 3 beds, 1 bathroom
24–29 Aug
Top guest favourite
Home in Highland
Cliffside Luxury: Hot Tub, Sun & River Views!
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
14–19 Jul
Guest favourite
Apartment in Poughkeepsie
Spacious and stylish entire one bedroom apartment.
4.97 out of 5 average rating, 378 reviews, 1 bedroom, 4 beds, 1 bathroom
19–24 Jul
Top guest favourite
Guest house in Hyde Park
Modern cottage with Hudson River view
4.99 out of 5 average rating, 790 reviews, 1 bed, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Home in Hyde Park
Wooded Rhinebeck-Beacon area Escape w/Outdoor Spa
4.99 out of 5 average rating, 80 reviews, 2 bedrooms, 4 beds, 2.5 bathrooms
14–19 Jul
Top guest favourite
Home in Staatsburg
Boulder Tree House
4.99 out of 5 average rating, 131 reviews, 1 bedroom, 2 beds, 2 bathrooms
6–11 Aug
Top guest favourite
Room in Hyde Park
Scandinavian Design Dutchess County - 1 of 3 rooms
4.96 out of 5 average rating, 681 reviews, 1 king bed, 1 bathroom
2–7 Aug
Top guest favourite
Home in New Paltz
The Gunks House
4.99 out of 5 average rating, 75 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
16–21 Jul
Top guest favourite
Home in Marlboro
Hudson Valley Farmhouse | Winery & Hiking Getaway
4.99 out of 5 average rating, 228 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
26–31 Jul
Top guest favourite
Home in New Paltz
Victorian Haven
4.96 out of 5 average rating, 812 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Jul
Guest favourite
Home in New Paltz
1875 School House near HV Rail Trail
4.96 out of 5 average rating, 84 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Top guest favourite
Home in Hyde Park
Charming Hyde Park Retreat|Minutes from Vanderbilt
5.0 out of 5 average rating, 34 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
16–21 Jul
Top guest favourite
Home in Rhinebeck
Eagle Rock House
5.0 out of 5 average rating, 257 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
18–23 Jul
Top guest favourite
Tiny home in Wallkill
Get Away to "Hygge" Tiny House on 75 Private Acres
4.99 out of 5 average rating, 366 reviews, 1 bed, 1 bathroom
19–24 Jul
Top guest favourite
Guest suite in New Paltz
Cozy New Paltz apartment (no cleaning fee)
4.91 out of 5 average rating, 1157 reviews, 1 bedroom, 1 bed, 1 bathroom
20–25 Sept
Guest favourite
Home in Highland
Splendid Isolation @ Extraordinary Country Retreat
4.97 out of 5 average rating, 78 reviews, 4 bedrooms, 4 beds, 5 bathrooms
7–14 Sept
Top guest favourite
Flat in New Paltz
Peaceful and Private Boutique Apartment *Pool*
4.94 out of 5 average rating, 401 reviews, 2 bedrooms, 2 beds, 1 bathroom
20–25 Jul