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Search results; Over 1,000 homes in Hillsdale

Guest favourite
Cabin in Town of Hillsdale
Rustic, peaceful and affordable cabin
4 bedrooms, 9 beds, 2 private bathrooms
30 Aug – 4 Sept
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4.8 out of 5 average rating, 343 reviews
Guest favourite
Rooms in Town of Hillsdale
Bellwether on Main, Passive House & AAC
2 bedrooms, 2 queen beds, 2 bathrooms
19–24 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Town of Hillsdale
Serene Suite: Hudson & Berkshires, Walk to Brewery
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 257 reviews
Top guest favourite
Place to stay in Town of Hillsdale
Sun Filled Historic Retreat | Berkshires & Hudson
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
4.94 out of 5 average rating, 101 reviews
Guest favourite
Home in Town of Hillsdale
Historic 1850s "The Bell House" with Private Pool
5 bedrooms, 5 beds, 4.5 bathrooms
26–31 Oct
5.0 out of 5 average rating, 16 reviews
Guest favourite
Cabin in Town of Hillsdale
Secluded Mountain Getaway with Swimming Pond.
4 bedrooms, 4 queen beds, 3 bathrooms
13–18 Sept
4.91 out of 5 average rating, 128 reviews
Top guest favourite
Barn in Town of Hillsdale
Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna
3 bedrooms, 3 beds, 2 bathrooms
30 Aug – 4 Sept
4.97 out of 5 average rating, 180 reviews
Top guest favourite
Home in Town of Hillsdale
Gorgeous Mountain Views Retreat: Family & Nature
4 bedrooms, 5 beds, 2.5 bathrooms
13–18 Sept
4.98 out of 5 average rating, 80 reviews
Top guest favourite
Home in Town of Hillsdale
Private unit in shared 1830 Farmhouse
2 bedrooms, 2 beds, 1 bathroom
29 Aug – 3 Sept
5.0 out of 5 average rating, 41 reviews
Home in Town of Hillsdale
Saltwater Pool - Hudson Valley Escape on 19 acres
3 bedrooms, 6 beds, 2.5 bathrooms
23–28 Aug
New place to stay
Superhost
Home in Town of Hillsdale
Quaint center of town Farmhouse
2 bedrooms, 3 beds, 1 bathroom
12–17 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Guest suite in Town of Hillsdale
The Barn @ Althouse - Higgins
2 bedrooms, 3 beds, 1 bathroom
14–19 Aug
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Home in Hudson
Chic Hudson Farmhouse w/ Fireplace & Porch
3 bedrooms, 3 beds, 1.5 bathrooms
16–21 Aug
4.98 out of 5 average rating, 121 reviews
Top guest favourite
Barn in Town of Hillsdale
Blue Door Barn - Pond and Sweeping Views
1 bedroom, 2 beds, 1 bathroom
17–22 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Loft in Great Barrington
The Old Red Barn
1 bedroom, 1 queen bed, 1 bathroom
8–13 Sept
4.99 out of 5 average rating, 366 reviews
Guest favourite
Farm stay in Town of Hillsdale
FARM HOUSE on Old Horse Farm!
4 bedrooms, 7 beds, 2.5 bathrooms
12–17 Aug
4.98 out of 5 average rating, 81 reviews
Top guest favourite
Tiny home in Chatham
Peaceful Tiny House Escape by Hudson & Berkshires
2 bedrooms, 2 queen beds, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 282 reviews
Top guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.99 out of 5 average rating, 313 reviews
Top guest favourite
Guest house in Athens
Athens Cottage
2 bedrooms, 3 beds, 1 bathroom
21–26 Sept
4.97 out of 5 average rating, 72 reviews