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Search results; Over 1,000 homes in Highland

Guest favourite
Home in Highland
Life in Color, Live Art Home
3 bedrooms, 3 beds, 2 private bathrooms
23–28 Aug
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4.79 out of 5 average rating, 52 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
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
Flat in Highland
View on Vineyard.
1 bedroom, 1 queen bed, 1 bathroom
21–26 Aug
4.92 out of 5 average rating, 13 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
Guest favourite
Home in Highland
Modern Stylish Farmhouse
2 bedrooms, 3 beds, 1 bathroom
7–12 Aug
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Room in Poughkeepsie
Hudson Pond · Garden Queen Suite · GF Breakfast
1 queen bed, 1 bathroom
31 Aug – 6 Sept
4.99 out of 5 average rating, 163 reviews
Top guest favourite
Cottage in Hyde Park
Cozy Historic Hyde Park Cottage - Near CIA & River
3 bedrooms, 3 beds, 1.5 bathrooms
9–14 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in New Paltz
Cozy New Paltz Escape Walk to Town, Trails & Shops
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 47 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
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, 383 reviews
Top guest favourite
Guest house in New Paltz
The Pool House
2 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Home in Hyde Park
Wooded Rhinebeck-Beacon area Escape w/Outdoor Spa
2 bedrooms, 4 beds, 2.5 bathrooms
15–20 Aug
4.99 out of 5 average rating, 82 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
Top guest favourite
Home in Staatsburg
Boulder Tree House
1 bedroom, 2 beds, 2 bathrooms
7–12 Nov
4.99 out of 5 average rating, 134 reviews
Top guest favourite
Flat in Marlboro
Cliff Top at Turtle Rock
1 bedroom, 1 queen bed, 1 bathroom
15–20 Aug
4.97 out of 5 average rating, 451 reviews
Top guest favourite
Home in Accord
Accord River House
2 bedrooms, 2 queen beds, 2 bathrooms
9–14 Aug
4.99 out of 5 average rating, 102 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
Top guest favourite
Home in Poughkeepsie
Beautiful, Fun, Spacious 5 Acre Family Retreat
3 bedrooms, 7 beds, 2.5 bathrooms
10–15 Aug
4.93 out of 5 average rating, 111 reviews