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Search results; Over 1,000 homes in Hillsdale

Descriptions are based on details hosts provide
Top guest favourite
Barn in Town of Hillsdale
Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna
3 bedrooms, 3 beds, 2 private bathrooms
12–17 Aug
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4.97 out of 5 average rating, 178 reviews
Top guest favourite
Place to stay in Town of Hillsdale
Sun Filled Historic Retreat | Berkshires & Hudson
4.94 out of 5 average rating, 95 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Place to stay in Town of Hillsdale
Bellwether on Main, Passive House & AAC
2 bedrooms, 2 beds, 2 bathrooms
21–26 Jul
Top guest favourite
Flat in Town of Hillsdale
Serene Suite: Hudson & Berkshires, Walk to Brewery
4.98 out of 5 average rating, 249 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Top guest favourite
Home in Town of Hillsdale
1830 farmhouse near the Berkshires
5.0 out of 5 average rating, 37 reviews, 2 bedrooms, 2 beds, 1 bathroom
18–23 Jul
Guest favourite
Cabin in Town of Hillsdale
Tory Hill Cabin; (North Mountain Cottages)
4.9 out of 5 average rating, 178 reviews, 3 bedrooms, 3 beds, 1 bathroom
13–18 Sept
Guest favourite
Guest suite in Town of Hillsdale
Overnight at Althouse-Higgins
4.98 out of 5 average rating, 142 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Top guest favourite
Home in Town of Hillsdale
Gorgeous Mountain Views Retreat: Family & Nature
4.97 out of 5 average rating, 78 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
26–31 Jul
Top guest favourite
Home in Hudson
Chic Hudson Farmhouse w/ Fireplace & Porch
4.98 out of 5 average rating, 120 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
2–7 Aug
Guest favourite
Home in Copake
Fireplace, fire pit, and lake access
4.97 out of 5 average rating, 76 reviews, 3 bedrooms, 3 beds, 2 bathrooms
3–8 Aug
Superhost
Home in Town of Hillsdale
Newly renovated between Hudson and the Berkshires
2 bedrooms, 3 beds, 1 bathroom
15–20 Jul
Guest favourite
Home in Town of Hillsdale
Restored 1850s estate with a private pool
5.0 out of 5 average rating, 14 reviews, 5 bedrooms, 5 beds, 4.5 bathrooms
12–17 Oct
Top guest favourite
Home in Town of Hillsdale
Meadowland Farmhouse — 5 minutes from town
5.0 out of 5 average rating, 22 reviews, 3 bedrooms, 5 beds, 2 bathrooms
17–22 Jul
Top guest favourite
Loft in Great Barrington
The Old Red Barn
4.99 out of 5 average rating, 364 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Sept
Top guest favourite
Barn in New Marlborough
Hartsville Barn in the Berkshires
4.98 out of 5 average rating, 41 reviews, 2 bedrooms, 2 beds, 1 bathroom
14–19 Sept
Guest favourite
Home in Copake
Copake Retreat
4.9 out of 5 average rating, 139 reviews, 3 bedrooms, 4 beds, 2 bathrooms
27 Jul – 1 Aug
Top guest favourite
Home in Salisbury
Greystone at Twin Lakes
4.99 out of 5 average rating, 67 reviews, 3 bedrooms, 3 beds, 1 bathroom
24–29 Aug
Top guest favourite
Home in Copake Lake
Waterfront home with a private dock
5.0 out of 5 average rating, 14 reviews, 3 bedrooms, 5 beds, 2 bathrooms
3–8 Aug
Guest favourite
Cabin in Town of Hillsdale
Secluded Mountain Getaway with Swimming Pond.
4.91 out of 5 average rating, 128 reviews, 4 bedrooms, 4 beds, 3 bathrooms
13–18 Sept