filters

Search results; Over 1,000 homes in Highland

Guest favourite
Guest suite in Highland
Peaceful Home (full kitchen, washer/dryer)
1 bedroom, 4 beds, 1 private bathroom
7–12 Sept
,
4.87 out of 5 average rating, 358 reviews
Guest favourite
Home in Highland
VIEWS on Hudson River / Luxury Modern Home
4 bedrooms, 5 beds, 3 bathrooms
18–23 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Highland
Two Tillson
2 bedrooms, 2 queen beds, 2.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in Highland
Cliffside Luxury: Hot Tub, Sun & River Views!
3 bedrooms, 5 beds, 2.5 bathrooms
10–15 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
6–11 Sept
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
Top 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, 384 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
Tiny home in New Paltz
Hudson Valley Tiny House
1 bed, 1 bathroom
13–18 Aug
4.99 out of 5 average rating, 906 reviews
Guest favourite
Flat in Poughkeepsie
3 Bdrm. Near Hudson Valley Colleges & Attractions
3 bedrooms, 3 beds, 1 bathroom
16–21 Aug
4.93 out of 5 average rating, 394 reviews
Top guest favourite
Flat in Hyde Park
Private, cozy, clean, apartment in Hyde Park NY
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.94 out of 5 average rating, 54 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
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, 48 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 Hyde Park
Charming Hyde Park Retreat|Minutes from Vanderbilt
3 bedrooms, 3 queen beds, 1.5 bathrooms
11–16 Aug
5.0 out of 5 average rating, 35 reviews
Guest favourite
Home in Highland
Modern Stylish Farmhouse
2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Flat in Marlboro
Cliff Top at Turtle Rock
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.97 out of 5 average rating, 451 reviews
Top guest favourite
Home in Highland
Bedelle Farmhouse on the Farm
3 bedrooms, 4 beds, 1.5 bathrooms
9–14 Aug
5.0 out of 5 average rating, 22 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