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Search results; Over 1,000 homes in Highland

Top guest favourite
Guest suite in Highland
Peaceful Home (full kitchen, washer/dryer)
1 bedroom, 4 beds, 1 private bathroom
25–30 Jul
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4.87 out of 5 average rating, 356 reviews
Superhost
Home in Highland
VIEWS on Hudson River / Luxury Modern Home
New place to stay, 4 bedrooms, 5 beds, 3 bathrooms
20–25 Jul
Top guest favourite
Guest suite in Highland
Cozy Studio | Near World’s Longest Walkway Bridge
4.94 out of 5 average rating, 66 reviews, 1 bedroom, 3 beds, 1 bathroom
28 Aug – 2 Sept
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
20–25 Jul
Top guest favourite
Guest house in Hyde Park
Modern cottage with Hudson River view
4.99 out of 5 average rating, 792 reviews, 1 bed, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Apartment in Poughkeepsie
Spacious and stylish entire one bedroom apartment.
4.97 out of 5 average rating, 380 reviews, 1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Home in Marlboro
Hudson Valley Farmhouse | Winery & Hiking Getaway
4.99 out of 5 average rating, 229 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, 814 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Jul – 4 Aug
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 Poughkeepsie
Hudson Pond · Hideaway King Suite · GF Breakfast
4.97 out of 5 average rating, 240 reviews, 1 king bed, 1 bathroom
6–11 Aug
Top guest favourite
Cabin in Saugerties
Luxury Catskills A-Frame Cabin | Hot Tub & Sauna
5.0 out of 5 average rating, 145 reviews, 2 bedrooms, 2 beds, 2 bathrooms
30 Oct – 4 Nov
Top guest favourite
Flat in New Paltz
Modena Mad House
4.96 out of 5 average rating, 422 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Guest favourite
Cottage in New Paltz
Fun, Private, Rail Trail Cottage
4.9 out of 5 average rating, 58 reviews, 2 bedrooms, 3 beds, 1 bathroom
3–8 Aug
Top guest favourite
Tiny home in New Paltz
Hudson Valley Tiny House
4.99 out of 5 average rating, 899 reviews, 1 bed, 1 bathroom
2–7 Aug
Top guest favourite
Cottage in Clintondale
Blue Spruce Cottage
4.99 out of 5 average rating, 86 reviews, 2 bedrooms, 3 beds, 1 bathroom
13–18 Aug
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
26–31 Jul
Top guest favourite
Cottage in Clintondale
Old Mill Cottage - Upstate Mountain Views
4.97 out of 5 average rating, 395 reviews, 1 bedroom, 2 beds, 1 bathroom
9–14 Aug
Top guest favourite
Home in New Paltz
Cozy New Paltz Escape Walk to Town, Trails & Shops
5.0 out of 5 average rating, 39 reviews, 1 bedroom, 2 beds, 1 bathroom
23–28 Aug
Top guest favourite
Home in Highland
Hudson Valley Estate 90 min from NYC Pool&GameRoom
5.0 out of 5 average rating, 49 reviews, 4 bedrooms, 6 beds, 2.5 bathrooms
10–15 Aug