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Search results; Over 1,000 homes in Hillsdale

Descriptions are based on details hosts provide
Chalet in Town of Hillsdale
Natural Splendor: Forest Luxury Retreat
3 bedrooms, 4 beds, 4 private bathrooms
3–8 Oct
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4.86 out of 5 average rating, 65 reviews
Top guest favourite
Place to stay in Town of Hillsdale
Suite in an 1881 Victorian inn
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
4.94 out of 5 average rating, 95 reviews
Place to stay in Town of Hillsdale
Certified Passive House in walkable hamlet
2 bedrooms, 2 queen beds, 2 bathrooms
21–26 Jul
Top guest favourite
Flat in Town of Hillsdale
Serene Suite: Hudson & Berkshires, Walk to Brewery
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
4.98 out of 5 average rating, 249 reviews
Top guest favourite
Home in Town of Hillsdale
Private unit in shared 1830 Farmhouse
2 bedrooms, 2 beds, 1 bathroom
18–23 Jul
5.0 out of 5 average rating, 37 reviews
Guest favourite
Cabin in Town of Hillsdale
Fireplace, fire pit, and a tent-friendly yard
3 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.9 out of 5 average rating, 178 reviews
Guest favourite
Guest suite in Town of Hillsdale
Renovated 1845 building in the Berkshires
2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
4.98 out of 5 average rating, 142 reviews
Top guest favourite
Barn in Town of Hillsdale
15-acre hilltop with sauna and hot tub
3 bedrooms, 3 beds, 2 bathrooms
12–17 Aug
4.97 out of 5 average rating, 178 reviews
Top guest favourite
Home in Town of Hillsdale
Gorgeous Mountain Views Retreat: Family & Nature
4 bedrooms, 5 beds, 2.5 bathrooms
26–31 Jul
4.97 out of 5 average rating, 78 reviews
Top guest favourite
Home in Hudson
Chic Hudson Farmhouse w/ Fireplace & Porch
3 bedrooms, 3 beds, 1.5 bathrooms
2–7 Aug
4.98 out of 5 average rating, 120 reviews
Guest favourite
Home in Copake
Fireplace, fire pit, and lake access
3 bedrooms, 3 beds, 2 bathrooms
3–8 Aug
4.97 out of 5 average rating, 76 reviews
Superhost
Home in Town of Hillsdale
Quaint center of town Farmhouse
2 bedrooms, 3 beds, 1 bathroom
15–20 Jul
Guest favourite
Home in Town of Hillsdale
Restored 1850s estate with a private pool
5 bedrooms, 5 beds, 4.5 bathrooms
12–17 Oct
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Town of Hillsdale
Modern rustic farmhouse on 3 acres
3 bedrooms, 5 beds, 2 bathrooms
17–22 Jul
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Loft in Great Barrington
The Old Red Barn
1 bedroom, 1 queen bed, 1 bathroom
1–6 Sept
4.99 out of 5 average rating, 364 reviews
Top guest favourite
Barn in New Marlborough
1860s post-and-beam barn with a fire pit
2 bedrooms, 2 king beds, 1 bathroom
14–19 Sept
4.98 out of 5 average rating, 41 reviews
Guest favourite
Home in Copake
Copake Retreat
3 bedrooms, 4 beds, 2 bathrooms
27 Jul – 1 Aug
4.9 out of 5 average rating, 139 reviews
Top guest favourite
Home in Salisbury
Greystone at Twin Lakes
3 bedrooms, 3 beds, 1 bathroom
24–29 Aug
4.99 out of 5 average rating, 67 reviews
Top guest favourite
Home in Copake Lake
Waterfront home with a private dock
3 bedrooms, 5 beds, 2 bathrooms
3–8 Aug
5.0 out of 5 average rating, 14 reviews