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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
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4.87 out of 5 average rating, 357 reviews
Superhost
Home in Highland
VIEWS on Hudson River / Luxury Modern Home
5.0 out of 5 average rating, 6 reviews, 4 bedrooms, 5 beds, 3 bathrooms
18–23 Aug
Top guest favourite
Home in Highland
Cliffside Luxury: Hot Tub, Sun & River Views!
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
15–20 Aug
Top guest favourite
Guest suite in Highland
Cozy Studio | Near World’s Longest Walkway Bridge
4.94 out of 5 average rating, 69 reviews, 1 bedroom, 3 beds, 1 bathroom
31 Aug – 5 Sept
Home in Highland
7 Mi to The Walkway: Hudson Valley Adventure Base
4.8 out of 5 average rating, 5 reviews, 4 bedrooms, 7 beds, 1.5 bathrooms
4–9 Sept
Guest favourite
Home in Highland
Modern Stylish Farmhouse
5.0 out of 5 average rating, 23 reviews, 2 bedrooms, 3 beds, 1 bathroom
1–6 Aug
Home in Highland
Secluded House on 55 ac w/pool 5 Mins to New Paltz
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Room in Poughkeepsie
Hudson Pond · Hideaway King Suite · GF Breakfast
4.97 out of 5 average rating, 241 reviews, 1 king bed, 1 bathroom
21–26 Aug
Top guest favourite
Cottage in New Paltz
Stone House 1807. Comfort, Peace and Nature.
4.99 out of 5 average rating, 593 reviews, 2 bedrooms, 3 beds, 1 bathroom
8–13 Sept
Top guest favourite
Home in Highland
Hudson Valley Estate 90 min from NYC Pool&GameRoom
5.0 out of 5 average rating, 50 reviews, 4 bedrooms, 6 beds, 2.5 bathrooms
10–15 Aug
Top guest favourite
Home in New Paltz
The Gunks House
4.99 out of 5 average rating, 77 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Aug
Guest favourite
Camper van/Motorhome in New Paltz
Daisy - 2025 Airstream Under the Gunks
4.92 out of 5 average rating, 12 reviews, 1 bedroom, 2 beds, 1 bathroom
10–15 Aug
Top guest favourite
Cabin in Saugerties
Luxury Catskills A-Frame Cabin | Hot Tub & Sauna
5.0 out of 5 average rating, 147 reviews, 2 bedrooms, 2 beds, 2 bathrooms
2–7 Sept
Top guest favourite
Home in Hyde Park
Beautiful 3 bedroom home with Hudson River views
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 4 beds, 1 bathroom
18–23 Aug
Top guest favourite
Home in Highland
Bedelle Farmhouse on the Farm
5.0 out of 5 average rating, 20 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
1–6 Aug
Guest favourite
Home in Highland
Splendid Isolation @ Extraordinary Country Retreat
4.97 out of 5 average rating, 78 reviews, 4 bedrooms, 4 beds, 5 bathrooms
7–14 Sept
Top guest favourite
Home in New Paltz
Cozy New Paltz Escape Walk to Town, Trails & Shops
5.0 out of 5 average rating, 44 reviews, 1 bedroom, 2 beds, 1 bathroom
23–28 Aug
Guest favourite
Flat in Newburgh
Special Nest w Private Entrance River View Porches
4.89 out of 5 average rating, 268 reviews, 1 bedroom, 1 bed, 2 bathrooms
2–7 Nov
Top guest favourite
Home in Rosendale
Stylish Rosendale Escape by Shops & Trails
5.0 out of 5 average rating, 24 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
1–6 Aug