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Search results; Over 1,000 homes in Highland

Top guest favourite
Holiday home in Highland
Charming Vacation House w/ Pool & HotTub
3 bedrooms, 6 beds, 2.5 private bathrooms
8–13 Sept
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5.0 out of 5 average rating, 39 reviews
Top guest favourite
Home in Highland
VIEWS on Hudson River / Luxury Modern Home
4 bedrooms, 5 beds
23–28 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Highland
Two Tillson
2 bedrooms, 2 queen beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Guest suite in Highland
Cozy Studio | Near World’s Longest Walkway Bridge
1 bedroom, 3 beds
28 Aug – 2 Sept
4.94 out of 5 average rating, 71 reviews
Guest favourite
Flat in Highland
View on Vineyard.
1 bedroom, 1 queen bed
6–11 Sept
4.93 out of 5 average rating, 14 reviews
Top guest favourite
Home in Highland
Cliffside Luxury: Hot Tub, Sun & River Views!
3 bedrooms, 5 beds
29 Aug – 3 Sept
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
22–27 Aug
New place to stay
Top guest favourite
Cottage in Clintondale
Old Mill Cottage - Upstate Mountain Views
1 bedroom, 2 beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 401 reviews
Guest favourite
Home in Highland
Splendid Isolation @ Extraordinary Country Retreat
4 bedrooms, 4 beds
7–14 Sept
4.97 out of 5 average rating, 79 reviews
Top guest favourite
Room in Poughkeepsie
Hudson Pond · Garden Queen Suite · GF Breakfast
1 queen bed
11–16 Sept
4.99 out of 5 average rating, 169 reviews
Top guest favourite
Cottage in Hyde Park
Cozy Historic Hyde Park Cottage - Near CIA & River
3 bedrooms, 3 beds
6–11 Sept
5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in Highland
Modern Stylish Farmhouse
2 bedrooms, 3 beds
19–24 Aug
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Home in New Paltz
Victorian Haven
1 bedroom, 1 queen bed
27 Sept – 2 Oct
4.96 out of 5 average rating, 818 reviews
Top guest favourite
Home in New Paltz
Streamside Haven - Scenic and Walkable to Downtown
3 bedrooms, 3 beds
7–13 Sept
4.98 out of 5 average rating, 44 reviews
Top guest favourite
Guest house in New Paltz
The Pool House
2 beds
13–18 Sept
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Home in New Paltz
1875 School House near HV Rail Trail
2 bedrooms, 3 beds
20–25 Sept
4.97 out of 5 average rating, 88 reviews
Top guest favourite
Flat in New Paltz
Modena Mad House
1 bedroom, 1 queen bed
30 Aug – 4 Sept
4.96 out of 5 average rating, 424 reviews
Top guest favourite
Home in Highland
Bedelle Farmhouse on the Farm
3 bedrooms, 4 beds
23–28 Aug
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Cabin in Saugerties
Luxury Catskills A-Frame Cabin | Hot Tub & Sauna
2 bedrooms, 2 queen beds
13–18 Dec
4.99 out of 5 average rating, 155 reviews