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Search results; Over 1,000 homes in Hillsdale

Top guest favourite
Flat in Town of Hillsdale
Serene Suite: Hudson & Berkshires, Walk to Brewery
1 bedroom, 1 bed, 1 private bathroom
9–14 Aug
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4.98 out of 5 average rating, 252 reviews
Rooms in Town of Hillsdale
Bellwether on Main, Passive House & AAC
2 bedrooms, 2 queen beds, 2 bathrooms
2–7 Aug
Top guest favourite
Place to stay in Town of Hillsdale
Sun Filled Historic Retreat | Berkshires & Hudson
4.94 out of 5 average rating, 97 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Guest favourite
Home in Town of Hillsdale
Historic 1850s "The Bell House" with Private Pool
5.0 out of 5 average rating, 16 reviews, 5 bedrooms, 5 beds, 4.5 bathrooms
26–31 Oct
Home in Town of Hillsdale
Secluded 19-Acre Hudson Valley Escape w/ Pool
New place to stay, 3 bedrooms, 6 beds, 2.5 bathrooms
16–21 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
Top guest favourite
Home in Town of Hillsdale
Private unit in shared 1830 Farmhouse
5.0 out of 5 average rating, 38 reviews, 2 bedrooms, 2 beds, 1 bathroom
12–17 Aug
Top guest favourite
Barn in Town of Hillsdale
Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna
4.97 out of 5 average rating, 178 reviews, 3 bedrooms, 3 beds, 2 bathrooms
12–17 Aug
Guest favourite
Guest suite in Town of Hillsdale
Overnight at Althouse-Higgins
4.98 out of 5 average rating, 143 reviews, 2 bedrooms, 3 beds, 1 bathroom
1–6 Aug
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
Superhost
Home in Town of Hillsdale
Quaint center of town Farmhouse
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 3 beds, 1 bathroom
1–6 Aug
Guest favourite
Cabin in Town of Hillsdale
Cabin in the woods near Catamount Ski resort
4.88 out of 5 average rating, 186 reviews, 2 bedrooms, 3 beds, 2 bathrooms
31 Aug – 5 Sept
Guest favourite
Cottage in Craryville
Farm Cottage w/ Donkeys, Fire Pit & Wood Stove
4.91 out of 5 average rating, 594 reviews, 3 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
Top guest favourite
Home in Town of Hillsdale
Gorgeous Mountain Views Retreat: Family & Nature
4.97 out of 5 average rating, 79 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
23–28 Aug
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
10–15 Aug
Top guest favourite
Home in Town of Hillsdale
Sprawling Farmhouse + Cottage Perfect for Groups
5.0 out of 5 average rating, 58 reviews, 8 bedrooms, 10 beds, 4.5 bathrooms
10–15 Sept
Guest favourite
Home in Copake
Copake Retreat
4.92 out of 5 average rating, 140 reviews, 3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
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
24–29 Aug
Top guest favourite
Cabin in Town of Taghkanic
A Summer Reset. Rest. Reconnect. Upstate.
4.95 out of 5 average rating, 42 reviews, 2 bedrooms, 2 beds, 1 bathroom
28 Aug – 2 Sept