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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, 702 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, 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
19–24 Jul
Top guest favourite
Guest house in Hyde Park
Modern cottage with Hudson River view
4.99 out of 5 average rating, 791 reviews, 1 bed, 1 bathroom
30 Aug – 4 Sept
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
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
Room in Poughkeepsie
Hudson Pond · Hideaway King Suite · GF Breakfast
4.97 out of 5 average rating, 239 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
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
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
Flat in Marlboro
Cliff Top at Turtle Rock
4.97 out of 5 average rating, 448 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 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
2–7 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
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
24–29 Jul
Top guest favourite
Cottage in Hyde Park
Cozy Historic Hyde Park Cottage - Near CIA & River
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
31 Jul – 5 Aug
Top guest favourite
Home in New Paltz
Relaxing Chalet Getaway, 5 min to Main St
4.98 out of 5 average rating, 108 reviews, 4 bedrooms, 4 beds, 2.5 bathrooms
22–27 Aug
Top guest favourite
Home in Highland
Bedelle Farmhouse on the Farm
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
26–31 Jul
Top guest favourite
Home in Highland
Spacious 4BD Country Gem - Fire Pit & Chill Vibes
4.96 out of 5 average rating, 69 reviews, 4 bedrooms, 4 beds, 3.5 bathrooms
19–24 Jul