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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
4 bedrooms, 5 beds, 3 bathrooms
19–24 Jul
New place to stay
Top guest favourite
Guest suite in Highland
Cozy Studio | Near World’s Longest Walkway Bridge
1 bedroom, 3 beds, 1 bathroom
28 Aug – 2 Sept
4.94 out of 5 average rating, 66 reviews
Top guest favourite
Home in Highland
Cliffside Luxury: Hot Tub, Sun & River Views!
3 bedrooms, 5 beds, 2.5 bathrooms
19–24 Jul
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Guest house in Hyde Park
Modern cottage with Hudson River view
1 bed, 1 bathroom
30 Aug – 4 Sept
4.99 out of 5 average rating, 791 reviews
Guest favourite
Apartment in Poughkeepsie
Spacious and stylish entire one bedroom apartment.
1 bedroom, 4 beds, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 379 reviews
Guest favourite
Flat in Poughkeepsie
3 Bdrm. Near Hudson Valley Colleges & Attractions
3 bedrooms, 3 beds, 1 bathroom
26–31 Jul
4.93 out of 5 average rating, 394 reviews
Top guest favourite
Home in Staatsburg
Boulder Tree House
1 bedroom, 2 beds, 2 bathrooms
6–11 Aug
4.99 out of 5 average rating, 131 reviews
Top guest favourite
Home in Marlboro
Hudson Valley Farmhouse | Winery & Hiking Getaway
3 bedrooms, 4 beds, 2.5 bathrooms
26–31 Jul
4.99 out of 5 average rating, 229 reviews
Top guest favourite
Cottage in Hyde Park
Cozy Historic Hyde Park Cottage - Near CIA & River
3 bedrooms, 3 beds, 1.5 bathrooms
31 Jul – 5 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Tiny home in New Paltz
Hudson Valley Tiny House
1 bed, 1 bathroom
2–7 Aug
4.99 out of 5 average rating, 899 reviews
Top guest favourite
Home in Hyde Park
Wooded Rhinebeck-Beacon area Escape w/Outdoor Spa
2 bedrooms, 4 beds, 2.5 bathrooms
24–29 Jul
4.99 out of 5 average rating, 80 reviews
Top guest favourite
Home in Highland
Spacious 4BD Country Gem - Fire Pit & Chill Vibes
4 bedrooms, 4 queen beds, 3.5 bathrooms
19–24 Jul
4.96 out of 5 average rating, 69 reviews
Top guest favourite
Home in Highland
Hudson Valley Estate 90 min from NYC Pool&GameRoom
4 bedrooms, 6 beds, 2.5 bathrooms
21–26 Jul
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Flat in New Paltz
Modena Mad House
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
4.96 out of 5 average rating, 422 reviews
Top guest favourite
Home in New Paltz
Streamside Haven - Scenic and Walkable to Downtown
3 bedrooms, 3 beds, 1 bathroom
26–31 Jul
4.97 out of 5 average rating, 39 reviews
Top guest favourite
Home in Rhinebeck
Eagle Rock House
3 bedrooms, 3 beds, 2.5 bathrooms
2–7 Nov
5.0 out of 5 average rating, 257 reviews
Top guest favourite
Cottage in Clintondale
Old Mill Cottage - Upstate Mountain Views
1 bedroom, 2 beds, 1 bathroom
9–14 Aug
4.97 out of 5 average rating, 395 reviews
Top guest favourite
Home in New Paltz
Relaxing Chalet Getaway, 5 min to Main St
4 bedrooms, 4 beds, 2.5 bathrooms
22–27 Aug
4.98 out of 5 average rating, 108 reviews