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Search results; Over 1,000 homes in Highland

Guest favourite
Barn in Highland
Magical Charming 1850s Barn on Idyllic Former Farm
1 bedroom, 2 beds, 1 private bathroom
21–26 Aug
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4.93 out of 5 average rating, 102 reviews
Guest favourite
Home in Highland
VIEWS on Hudson River / Luxury Modern Home
4 bedrooms, 5 beds, 3 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Guest suite in Highland
Cozy Studio | Near World’s Longest Walkway Bridge
1 bedroom, 3 beds, 1 bathroom
31 Aug – 5 Sept
4.94 out of 5 average rating, 70 reviews
Top guest favourite
Home in Highland
Cliffside Luxury: Hot Tub, Sun & River Views!
3 bedrooms, 5 beds, 2.5 bathrooms
7–12 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Highland
Modern Stylish Farmhouse
2 bedrooms, 3 beds, 1 bathroom
6–11 Aug
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Room in Rhinecliff
Rhinecliff: King Room with Balcony
1 king bed, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 14 reviews
Guest favourite
Camper van/Motorhome in New Paltz
Daisy - 2025 Airstream Under the Gunks
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.93 out of 5 average rating, 14 reviews
Guest favourite
Tent in High Falls
Fern Forest Campsite
1 bedroom, 1 double bed, WC
9–14 Aug
4.89 out of 5 average rating, 219 reviews
Top guest favourite
Home in Highland
Spacious 4BD Country Gem - Fire Pit & Chill Vibes
4 bedrooms, 4 queen beds, 3.5 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 72 reviews
Home in Highland
Secluded House on 55 ac w/pool 5 Mins to New Paltz
3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
New place to stay
Top guest favourite
Cottage in Clintondale
Old Mill Cottage - Upstate Mountain Views
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 399 reviews
Guest favourite
Home in Highland
Splendid Isolation @ Extraordinary Country Retreat
4 bedrooms, 4 beds, 5 bathrooms
7–14 Sept
4.97 out of 5 average rating, 79 reviews
Top guest favourite
Flat in New Paltz
Modena Mad House
1 bedroom, 1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.96 out of 5 average rating, 423 reviews
Top guest favourite
Guest suite in Ulster Park
Sunny and Spacious Studio - a serene getaway
1 bedroom, 3 beds, 1 bathroom
16–21 Aug
4.95 out of 5 average rating, 152 reviews
Guest favourite
Apartment in Poughkeepsie
Spacious and stylish entire one bedroom apartment.
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 382 reviews
Guest favourite
Home in New Paltz
1875 School House near HV Rail Trail
2 bedrooms, 3 beds, 1 bathroom
14–19 Aug
4.97 out of 5 average rating, 87 reviews
Top guest favourite
Place to stay in Accord
Native Soul Stays, a wooded sauna retreat
1 bedroom, 1 king bed, No bathroom
14–19 Aug
4.96 out of 5 average rating, 305 reviews
Top guest favourite
Home in Highland
Hudson Valley Estate 90 min from NYC Pool&GameRoom
4 bedrooms, 6 beds, 2.5 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 51 reviews
Top guest favourite
Guest house in Hyde Park
Modern cottage with Hudson River view
1 bed, 1 bathroom
31 Oct – 5 Nov
4.99 out of 5 average rating, 797 reviews