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Search results; Over 1,000 homes in Hillsdale

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Top guest favourite
Barn in Town of Hillsdale
Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna
3 bedrooms, 3 beds, 2 private bathrooms
4–9 Oct
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4.97 out of 5 average rating, 185 reviews
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Top guest favourite
Rooms in Town of Hillsdale
Bellwether on Main, Passive House & AAC
2 bedrooms, 2 queen beds, 2 bathrooms
11–16 Oct
5.0 out of 5 average rating, 13 reviews
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Top guest favourite
Place to stay in Town of Hillsdale
Sun Filled Historic Retreat | Berkshires & Hudson
1 bedroom, 1 queen bed, 1 bathroom
18–23 Oct
4.94 out of 5 average rating, 109 reviews
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Top guest favourite
Flat in Town of Hillsdale
Serene Suite: Hudson & Berkshires, Walk to Brewery
1 bedroom, 1 queen bed, 1 bathroom
11–16 Oct
4.98 out of 5 average rating, 264 reviews
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Top guest favourite
Home in Town of Hillsdale
Sprawling Farmhouse Perfect for Large Groups
6 bedrooms, 7 beds, 3.5 bathrooms
29 Oct – 3 Nov
4.99 out of 5 average rating, 88 reviews
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Top guest favourite
Home in Town of Hillsdale
Private unit in shared 1830 Farmhouse
2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
5.0 out of 5 average rating, 44 reviews
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Top guest favourite
Flat in Town of Hillsdale
Perfect Apt near Berkshires, Hudson Valley
2 bedrooms, 2 beds, 1.5 bathrooms
22–29 Oct
4.96 out of 5 average rating, 102 reviews
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Cottage in Town of Hillsdale
Sunset Cottage at Breezy Hill Farm
2 bedrooms, 2 queen beds, 1 bathroom
4–9 Oct
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Top guest favourite
Home in Town of Hillsdale
Sprawling Farmhouse + Cottage Perfect for Groups
8 bedrooms, 10 beds, 4.5 bathrooms
29 Oct – 3 Nov
5.0 out of 5 average rating, 60 reviews
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Guest favourite
Farm stay in Town of Hillsdale
FARM HOUSE on Old Horse Farm!
4 bedrooms, 7 beds, 2.5 bathrooms
19–24 Oct
4.98 out of 5 average rating, 82 reviews
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Top guest favourite
Home in Town of Hillsdale
Renovated farmhouse with stunning views
5 bedrooms, 5 beds, 2.5 bathrooms
1–6 Feb
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Home in Town of Hillsdale
Gorgeous Mountain Views Retreat: Family & Nature
4 bedrooms, 5 beds, 2.5 bathrooms
1–6 Oct
4.98 out of 5 average rating, 83 reviews
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Guest favourite
Home in Town of Hillsdale
Meadowland Farmhouse — 5 minutes from town
3 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 25 reviews
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Guest favourite
Home in Town of Hillsdale
Three minutes to Catamount!
4 bedrooms, 5 beds, 2.5 bathrooms
1–6 Oct
4.88 out of 5 average rating, 41 reviews
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Top guest favourite
Cottage in Town of Hillsdale
Underhill Cottage
3 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
4.98 out of 5 average rating, 59 reviews
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Superhost
Barn in Town of Hillsdale
Historic 1850s Carriage House Studio @ Town Center
1 bedroom, 1 queen bed, 1 bathroom
26–31 Oct
4.86 out of 5 average rating, 21 reviews
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Guest favourite
Guest suite in Town of Hillsdale
Overnight at Althouse-Higgins
2 bedrooms, 3 beds, 1 bathroom
1–6 Oct
4.98 out of 5 average rating, 145 reviews
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Guest favourite
Home in Town of Hillsdale
Berkshire Mountain House
4 bedrooms, 8 beds, 3 bathrooms
1–6 Oct
4.94 out of 5 average rating, 34 reviews
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Superhost
Home in Town of Hillsdale
Quaint center of town Farmhouse
2 bedrooms, 3 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 3 reviews