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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
4.93 out of 5 average rating, 92 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
Top guest favourite
Flat in Town of Hillsdale
Serene Suite: Hudson & Berkshires, Walk to Brewery
4.98 out of 5 average rating, 247 reviews, 1 bedroom, 1 bed, 1 bathroom
25–30 Jul
Top guest favourite
Home in Town of Hillsdale
Private unit in shared 1830 Farmhouse
5.0 out of 5 average rating, 36 reviews, 2 bedrooms, 2 beds, 1 bathroom
18–23 Jul
Place to stay in Town of Hillsdale
Bellwether on Main, Passive House & AAC
2 bedrooms, 2 beds, 2 bathrooms
5–10 Jul
Guest favourite
Flat in Great Barrington
King Bed|Wi-Fi|2m Ski Resort|Berkshires
4.89 out of 5 average rating, 123 reviews, 1 bed, 1 bathroom
5–10 Jul
Guest favourite
Barn in Town of Hillsdale
Historic 1850s Carriage House Studio @ Town Center
4.93 out of 5 average rating, 14 reviews, 1 bedroom, 1 bed, 1 bathroom
18–23 Jul
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
7–12 Jul
Top guest favourite
Home in Town of Hillsdale
Gorgeous Mountain Views Retreat: Family & Nature
4.97 out of 5 average rating, 77 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
8–13 Jul
Top guest favourite
Home in Copake
Yellow Door House
4.92 out of 5 average rating, 92 reviews, 2 bedrooms, 2 beds, 1 bathroom
12–17 Nov
Top guest favourite
Home in Copake Lake
Waterside Private Retreat Home Near Copake Lake
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 5 beds, 2 bathrooms
6–11 Jul
Guest favourite
Cabin in Town of Hillsdale
Secluded Mountain Getaway with Swimming Pond.
4.91 out of 5 average rating, 127 reviews, 4 bedrooms, 4 beds, 3 bathrooms
13–18 Sept
Top guest favourite
Barn in Town of Hillsdale
Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna
4.97 out of 5 average rating, 175 reviews, 3 bedrooms, 3 beds, 2 bathrooms
12–17 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
31 Aug – 5 Sept
Top guest favourite
Home in Town of Hillsdale
Sprawling Farmhouse + Cottage Perfect for Groups
5.0 out of 5 average rating, 55 reviews, 8 bedrooms, 10 beds, 4.5 bathrooms
27 Aug – 1 Sept
Top guest favourite
Flat in Great Barrington
Private En Suite in Beautiful Victorian
4.95 out of 5 average rating, 416 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Oct
Top guest favourite
Home in Town of Ancram
It's Going To Be A Sunny Weekend By The Lake
4.99 out of 5 average rating, 170 reviews, 3 bedrooms, 4 beds, 1 bathroom
6–11 Jul
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 Ghent
The Wool House - Luxe Hudson Farmhouse on 3 acres
5.0 out of 5 average rating, 16 reviews, 4 bedrooms, 5 beds, 2 bathrooms
5–10 Jul