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Search results; Over 1,000 homes in Highland

Top guest favourite
Holiday home in Highland
Charming Vacation House w/ Pool & HotTub
3 bedrooms, 6 beds, 2.5 private bathrooms
8–13 Sept
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5.0 out of 5 average rating, 39 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, 8 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, 20 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
Home in Highland
Cliffside Luxury: Hot Tub, Sun & River Views!
3 bedrooms, 5 beds, 2.5 bathrooms
11–16 Aug
5.0 out of 5 average rating, 11 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
Superhost
Home in Highland
Peaceful Spacious 5 BR Family Home with a View
5 bedrooms, 7 beds, 4 bathrooms
16–21 Aug
New place to stay
Top guest favourite
Cottage in Hyde Park
Cozy Historic Hyde Park Cottage - Near CIA & River
3 bedrooms, 3 beds, 1.5 bathrooms
18–23 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Apartment in Poughkeepsie
Spacious and stylish entire one bedroom apartment.
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 384 reviews
Top guest favourite
Tiny home in New Paltz
Hudson Valley Tiny House
1 bed, 1 bathroom
30 Oct – 4 Nov
4.99 out of 5 average rating, 906 reviews
Home in Highland
7 Mi to The Walkway: Hudson Valley Adventure Base
4 bedrooms, 7 beds, 1.5 bathrooms
7–12 Sept
4.83 out of 5 average rating, 6 reviews
Guest favourite
Home in Highland
Modern Stylish Farmhouse
2 bedrooms, 3 beds, 1 bathroom
12–17 Aug
5.0 out of 5 average rating, 23 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
Home in Hyde Park
Luxe Mountain Getaway on Private Rd Near Rhinebeck
3 bedrooms, 5 beds, 3.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 3 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, 48 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
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, 165 reviews
Guest favourite
Camper van/Motorhome in New Paltz
Penelope, 1969 Airstream
1 bedroom, 2 king beds, WC
30 Aug – 4 Sept
4.96 out of 5 average rating, 147 reviews
Top guest favourite
Home in New Paltz
Beautiful house under the Gunks
3 bedrooms, 4 beds, 2.5 bathrooms
8–13 Nov
4.97 out of 5 average rating, 60 reviews