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Search results; Over 1,000 homes in Hillsdale

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, 94 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, 249 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, 37 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
23–28 Jul
Superhost
Barn in Town of Hillsdale
Historic 1850s Carriage House Studio @ Town Center
4.87 out of 5 average rating, 15 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
19–24 Jul
Guest favourite
Home in Town of Hillsdale
Berkshire Mountain House
4.94 out of 5 average rating, 34 reviews, 4 bedrooms, 8 beds, 3 bathrooms
1–6 Aug
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
Home in Town of Hillsdale
Historic 1850s "The Bell House" with Private Pool
5.0 out of 5 average rating, 13 reviews, 5 bedrooms, 5 beds, 4.5 bathrooms
12–17 Oct
Top guest favourite
Home in Town of Hillsdale
Sprawling Farmhouse + Cottage Perfect for Groups
5.0 out of 5 average rating, 56 reviews, 8 bedrooms, 10 beds, 4.5 bathrooms
10–15 Sept
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
Flat in Great Barrington
King Bed|Wi-Fi|2m Ski Resort|Studio|Berkshires
4.93 out of 5 average rating, 164 reviews, 1 bed, 1 bathroom
19–24 Jul
Top guest favourite
Home in Copake Lake
Waterside Private Retreat Home Near Copake Lake
5.0 out of 5 average rating, 14 reviews, 3 bedrooms, 5 beds, 2 bathrooms
31 Jul – 5 Aug
Top guest favourite
Home in Town of Hillsdale
Sprawling Farmhouse Perfect for Large Groups
4.99 out of 5 average rating, 88 reviews, 6 bedrooms, 7 beds, 3.5 bathrooms
10–15 Sept
Top guest favourite
Home in Copake Lake
Waterfront Retreat in a woodsy haven
5.0 out of 5 average rating, 11 reviews, 4 bedrooms, 5 beds, 3 bathrooms
31 Aug – 5 Sept
Guest favourite
Home in Town of Hillsdale
Serene Hillsdale Cottage Amped with Tech and Wifi
4.97 out of 5 average rating, 29 reviews, 4 bedrooms, 6 beds, 2.5 bathrooms
13–18 Jul
Top guest favourite
Cabin in Town of Taghkanic
A Summer Reset. Rest. Reconnect. Upstate.
4.95 out of 5 average rating, 41 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Aug – 1 Sept
Guest favourite
Home in Town of Hillsdale
Hillsdale Neighbors | Valley Views • Firepit
4.88 out of 5 average rating, 8 reviews, 4 bedrooms, 4 beds, 3 bathrooms
7–12 Sept