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Search results; Over 1,000 homes in Hillsdale

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
Sun Filled Historic Retreat | Berkshires & Hudson
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.94 out of 5 average rating, 106 reviews
Top guest favourite
Flat in Town of Hillsdale
Serene Suite: Hudson & Berkshires, Walk to Brewery
1 bedroom, 1 queen bed, 1 bathroom
26 Sept – 1 Oct
4.98 out of 5 average rating, 261 reviews
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Home in Town of Hillsdale
Private unit in shared 1830 Farmhouse
2 bedrooms, 2 beds, 1 bathroom
12–17 Sept
5.0 out of 5 average rating, 43 reviews
Top guest favourite
Rooms in Town of Hillsdale
Bellwether on Main, Passive House & AAC
2 bedrooms, 2 queen beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 10 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
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, 83 reviews
Superhost
Barn in Town of Hillsdale
Historic 1850s Carriage House Studio @ Town Center
1 bedroom, 1 queen bed, 1 bathroom
14–19 Sept
4.89 out of 5 average rating, 19 reviews
Top guest favourite
Barn in Town of Hillsdale
Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.97 out of 5 average rating, 184 reviews
Guest favourite
Guest suite in Town of Hillsdale
Overnight at Althouse-Higgins
2 bedrooms, 3 beds, 1 bathroom
6–11 Sept
4.98 out of 5 average rating, 143 reviews
Guest favourite
Home in Town of Hillsdale
Berkshire Mountain House
4 bedrooms, 8 beds, 3 bathrooms
6–11 Sept
4.94 out of 5 average rating, 34 reviews
Top guest favourite
Home in Town of Hillsdale
Lakefront close to ski & shopping
3 bedrooms, 8 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 69 reviews
Top guest favourite
Cottage in Town of Hillsdale
Underhill Cottage
3 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
4.98 out of 5 average rating, 59 reviews
Top guest favourite
Loft in Great Barrington
The Old Red Barn
1 bedroom, 1 queen bed, 1 bathroom
26 Sept – 1 Oct
4.99 out of 5 average rating, 370 reviews
Guest favourite
Home in Town of Hillsdale
Modern Lux Estate+Guesthouse, Swimming Pond
6 bedrooms, 6 beds, 7.5 bathrooms
7–13 Sept
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Home in Great Barrington
Seekonk Hill
2 bedrooms, 2 queen beds, 2 bathrooms
26–31 Oct
4.98 out of 5 average rating, 46 reviews
Top guest favourite
Cabin in Town of Taghkanic
A Summer Reset. Rest. Reconnect. Upstate.
2 bedrooms, 2 beds, 1 bathroom
26–31 Oct
4.96 out of 5 average rating, 47 reviews
Guest favourite
Cottage in Copake
Modern Mid-Century House -Hike, Kayak, Lake Access
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.92 out of 5 average rating, 132 reviews
Guest favourite
Home in Town of Hillsdale
Lake Front House with Rustic and Charming Feel
3 bedrooms, 4 beds, 1.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 8 reviews