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Search results; Over 1,000 homes in Hillsdale

Guest favourite
Guest suite in Town of Hillsdale
Overnight at Althouse-Higgins
2 bedrooms, 3 beds, 1 private bathroom
9–14 Aug
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4.98 out of 5 average rating, 143 reviews
Top guest favourite
Flat in Town of Hillsdale
Serene Suite: Hudson & Berkshires, Walk to Brewery
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
4.98 out of 5 average rating, 255 reviews
Top guest favourite
Place to stay in Town of Hillsdale
Sun Filled Historic Retreat | Berkshires & Hudson
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
4.94 out of 5 average rating, 100 reviews
Guest favourite
Cabin in Town of Hillsdale
Secluded Mountain Getaway with Swimming Pond.
4 bedrooms, 4 queen beds, 3 bathrooms
13–18 Sept
4.91 out of 5 average rating, 128 reviews
Superhost
Barn in Town of Hillsdale
Historic 1850s Carriage House Studio @ Town Center
1 bedroom, 1 queen bed, 1 bathroom
22–27 Aug
4.88 out of 5 average rating, 17 reviews
Rooms in Town of Hillsdale
Bellwether on Main, Passive House & AAC
2 bedrooms, 2 queen beds, 2 bathrooms
9–14 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Town of Hillsdale
Private unit in shared 1830 Farmhouse
2 bedrooms, 2 beds, 1 bathroom
12–17 Aug
5.0 out of 5 average rating, 39 reviews
Guest favourite
Home in Town of Hillsdale
Historic 1850s "The Bell House" with Private Pool
5 bedrooms, 5 beds, 4.5 bathrooms
26–31 Oct
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Barn in Town of Hillsdale
Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna
3 bedrooms, 3 beds, 2 bathrooms
12–17 Aug
4.97 out of 5 average rating, 179 reviews
Guest favourite
Cabin in Town of Hillsdale
Cabin in the woods near Catamount Ski resort
2 bedrooms, 3 beds, 2 bathrooms
31 Aug – 5 Sept
4.88 out of 5 average rating, 187 reviews
Home in Town of Hillsdale
Secluded 19-Acre Hudson Valley Escape w/ Pool
3 bedrooms, 6 beds, 2.5 bathrooms
23–28 Aug
New place to stay
Home in Town of Hillsdale
Lakefront Escape w/ Dock! Hudson Valley Home
2 bedrooms, 2 beds, 1 bathroom
28 Aug – 2 Sept
New place to stay
Top guest favourite
Barn in Town of Hillsdale
Blue Door Barn - Pond and Sweeping Views
1 bedroom, 2 beds, 1 bathroom
5–10 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Town of Hillsdale
Berkshire Mountain House
4 bedrooms, 8 beds, 3 bathrooms
31 Aug – 5 Sept
4.94 out of 5 average rating, 34 reviews
Guest favourite
Flat in Great Barrington
King Bed|ADA ROOM|2m Ski Resort
1 king bed, 1 bathroom
23–28 Aug
4.9 out of 5 average rating, 69 reviews
Guest favourite
Flat in Great Barrington
King Bed|Wi-Fi|2m Ski Resort|Berkshires
1 king bed, 1 bathroom
23–28 Aug
4.88 out of 5 average rating, 130 reviews
Guest favourite
Room in Town of Hillsdale
Sweet Butter and Cream Guestroom
1 double bed, 1.5 bathrooms
4–9 Aug
4.81 out of 5 average rating, 75 reviews
Top guest favourite
Home in Town of Hillsdale
Gorgeous Mountain Views Retreat: Family & Nature
4 bedrooms, 5 beds, 2.5 bathrooms
13–18 Aug
4.98 out of 5 average rating, 80 reviews
Top guest favourite
Cottage in Town of Hillsdale
Underhill Cottage
3 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
4.98 out of 5 average rating, 59 reviews