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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
23–28 Aug
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4.98 out of 5 average rating, 258 reviews
Guest favourite
Rooms in Town of Hillsdale
Bellwether on Main, Passive House & AAC
2 bedrooms, 2 queen beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Place to stay in Town of Hillsdale
Sun Filled Historic Retreat | Berkshires & Hudson
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.94 out of 5 average rating, 102 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, 18 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
Top guest favourite
Home in Town of Hillsdale
Private unit in shared 1830 Farmhouse
2 bedrooms, 2 beds, 1 bathroom
29 Aug – 3 Sept
5.0 out of 5 average rating, 41 reviews
Top guest favourite
Barn in Town of Hillsdale
Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.97 out of 5 average rating, 181 reviews
Top guest favourite
Home in Town of Hillsdale
Gorgeous Mountain Views Retreat: Family & Nature
4 bedrooms, 5 beds, 2.5 bathrooms
13–18 Sept
4.98 out of 5 average rating, 81 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
Top guest favourite
Guest suite in Town of Hillsdale
The Barn @ Althouse - Higgins
2 bedrooms, 3 beds, 1 bathroom
22–27 Aug
5.0 out of 5 average rating, 29 reviews
Flat in Egremont
Berkshires Charm Private Apartment
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
New place to stay
Guest favourite
Farm stay in Town of Hillsdale
FARM HOUSE on Old Horse Farm!
4 bedrooms, 7 beds, 2.5 bathrooms
27 Aug – 1 Sept
4.98 out of 5 average rating, 82 reviews
Superhost
Home in Town of Hillsdale
Quaint center of town Farmhouse
2 bedrooms, 3 beds, 1 bathroom
19–24 Aug
5.0 out of 5 average rating, 3 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
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
Guest favourite
Cabin in Town of Hillsdale
Cabin in the woods near Catamount Ski resort
2 bedrooms, 3 beds, 2 bathrooms
15–20 Sept
4.88 out of 5 average rating, 187 reviews
Cabin in Town of Hillsdale
Tory Hill Cabin; (North Mountain Cottages)
3 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.9 out of 5 average rating, 179 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, 73 reviews
Guest favourite
Home in Town of Hillsdale
Three minutes to Catamount!
4 bedrooms, 5 beds, 2.5 bathrooms
1–6 Sept
4.88 out of 5 average rating, 40 reviews