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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
7–12 Sept
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4.97 out of 5 average rating, 181 reviews
Guest favourite
Rooms in Town of Hillsdale
Bellwether on Main, Passive House & AAC
2 bedrooms, 2 queen beds, 2 bathrooms
19–24 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Town of Hillsdale
Serene Suite: Hudson & Berkshires, Walk to Brewery
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 257 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
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
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
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
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, 80 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
Top guest favourite
Home in Hudson
Chic Hudson Farmhouse w/ Fireplace & Porch
3 bedrooms, 3 beds, 1.5 bathrooms
28 Aug – 2 Sept
4.98 out of 5 average rating, 121 reviews
Superhost
Home in Town of Hillsdale
Quaint center of town Farmhouse
2 bedrooms, 3 beds, 1 bathroom
15–20 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Copake Lake
Waterside Private Retreat Home Near Copake Lake
3 bedrooms, 5 beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 19 reviews
Guest favourite
Home in Town of Taghkanic
Wildflower Cottage near Hudson w/ Fire Pit & AC
3 bedrooms, 4 beds, 2 bathrooms
18–23 Aug
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Guest house in Athens
Athens Cottage
2 bedrooms, 3 beds, 1 bathroom
21–26 Sept
4.97 out of 5 average rating, 73 reviews
Top guest favourite
Home in Salisbury
Greystone at Twin Lakes
3 bedrooms, 3 beds, 1 bathroom
24–29 Aug
4.97 out of 5 average rating, 70 reviews
Top guest favourite
Barn in Town of Hillsdale
Blue Door Barn - Pond and Sweeping Views
1 bedroom, 2 beds, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 12 reviews
Guest favourite
Farm stay in Town of Hillsdale
FARM HOUSE on Old Horse Farm!
4 bedrooms, 7 beds, 2.5 bathrooms
15–20 Aug
4.98 out of 5 average rating, 82 reviews
Top guest favourite
Cottage in Great Barrington
Artist Cottage
1 bedroom, 1 queen bed, 2 bathrooms
30 Oct – 4 Nov
4.93 out of 5 average rating, 350 reviews
Top guest favourite
Barn in New Marlborough
Hartsville Barn in the Berkshires
2 bedrooms, 2 king beds, 1 bathroom
27 Oct – 1 Nov
4.98 out of 5 average rating, 45 reviews