filters

Search results; Over 1,000 homes in Hillsdale

Guest favourite
Cabin in Town of Hillsdale
Secluded Mountain Getaway with Swimming Pond.
4 bedrooms, 4 beds, 3 private bathrooms
13–18 Sept
,
4.91 out of 5 average rating, 128 reviews
Top guest favourite
Flat in Town of Hillsdale
Serene Suite: Hudson & Berkshires, Walk to Brewery
1 bedroom, 1 queen bed
23–28 Aug
4.98 out of 5 average rating, 256 reviews
Top guest favourite
Place to stay in Town of Hillsdale
Sun Filled Historic Retreat | Berkshires & Hudson
1 bedroom, 1 queen bed
16–21 Aug
4.94 out of 5 average rating, 101 reviews
Rooms in Town of Hillsdale
Bellwether on Main, Passive House & AAC
2 bedrooms, 2 queen beds
19–24 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Town of Hillsdale
Historic 1850s "The Bell House" with Private Pool
5 bedrooms, 5 beds
26–31 Oct
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Town of Hillsdale
Private unit in shared 1830 Farmhouse
2 bedrooms, 2 beds
12–17 Aug
5.0 out of 5 average rating, 40 reviews
Top guest favourite
Barn in Town of Hillsdale
Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna
3 bedrooms, 3 beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 180 reviews
Home in Town of Hillsdale
Secluded 19-Acre Hudson Valley Escape w/ Pool
3 bedrooms, 6 beds
23–28 Aug
New place to stay
Guest favourite
Guest suite in Town of Hillsdale
Overnight at Althouse-Higgins
2 bedrooms, 3 beds
23–28 Aug
4.98 out of 5 average rating, 143 reviews
Top guest favourite
Home in Town of Hillsdale
Gorgeous Mountain Views Retreat: Family & Nature
4 bedrooms, 5 beds
23–28 Aug
4.98 out of 5 average rating, 80 reviews
Guest favourite
Home in Town of Hillsdale
Berkshire Mountain House
4 bedrooms, 8 beds
31 Aug – 5 Sept
4.94 out of 5 average rating, 34 reviews
Guest favourite
Cabin in Town of Hillsdale
Cabin in the woods near Catamount Ski resort
2 bedrooms, 3 beds
9–14 Sept
4.88 out of 5 average rating, 187 reviews
Superhost
Barn in Town of Hillsdale
Historic 1850s Carriage House Studio @ Town Center
1 bedroom, 1 queen bed
22–27 Aug
4.88 out of 5 average rating, 17 reviews
Top guest favourite
Cottage in Town of Hillsdale
Underhill Cottage
3 bedrooms, 3 beds
28 Sept – 3 Oct
4.98 out of 5 average rating, 59 reviews
Superhost
Home in Town of Hillsdale
Quaint center of town Farmhouse
2 bedrooms, 3 beds
11–16 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Farm stay in Town of Hillsdale
FARM HOUSE on Old Horse Farm!
4 bedrooms, 7 beds
10–15 Aug
4.98 out of 5 average rating, 81 reviews
Top guest favourite
Home in Town of Hillsdale
Sprawling Farmhouse + Cottage Perfect for Groups
8 bedrooms, 10 beds
29 Oct – 3 Nov
5.0 out of 5 average rating, 59 reviews
Guest favourite
Room in Town of Ancram
The Doodletown
1 double bed
17–22 Aug
4.96 out of 5 average rating, 212 reviews
Top guest favourite
Tiny home in Chatham
Peaceful Tiny House Escape by Hudson & Berkshires
2 bedrooms, 2 queen beds
13–18 Sept
4.99 out of 5 average rating, 282 reviews