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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
1 bedroom, 1 queen bed, 1 bathroom
19–24 Jul
4.94 out of 5 average rating, 94 reviews
Place to stay in Town of Hillsdale
Bellwether on Main, Passive House & AAC
2 bedrooms, 2 queen beds, 2 bathrooms
23–28 Jul
Guest favourite
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, 178 reviews
Top guest favourite
Flat in Town of Hillsdale
Serene Suite: Hudson & Berkshires, Walk to Brewery
1 bedroom, 1 queen bed, 1 bathroom
25–30 Jul
4.98 out of 5 average rating, 249 reviews
Top guest favourite
Home in Town of Hillsdale
Private unit in shared 1830 Farmhouse
2 bedrooms, 2 beds, 1 bathroom
18–23 Jul
5.0 out of 5 average rating, 37 reviews
Guest favourite
Home in Town of Hillsdale
Berkshire Mountain House
4 bedrooms, 8 beds, 3 bathrooms
1–6 Aug
4.94 out of 5 average rating, 34 reviews
Top guest favourite
Home in Town of Hillsdale
Gorgeous Mountain Views Retreat: Family & Nature
4 bedrooms, 5 beds, 2.5 bathrooms
26–31 Jul
4.97 out of 5 average rating, 77 reviews
Guest favourite
Home in Town of Hillsdale
Historic 1850s "The Bell House" with Private Pool
5 bedrooms, 5 beds, 4.5 bathrooms
12–17 Oct
5.0 out of 5 average rating, 13 reviews
Guest favourite
Home in Copake
Modern Rustic Getaway | Quiet | Wifi |Parking
3 bedrooms, 3 beds, 2 bathrooms
25–30 Jul
4.97 out of 5 average rating, 75 reviews
Guest favourite
Guest suite in Town of Hillsdale
Overnight at Althouse-Higgins
2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
4.98 out of 5 average rating, 142 reviews
Top guest favourite
Home in Hudson
Chic Hudson Farmhouse w/ Fireplace & Porch
3 bedrooms, 3 beds, 1.5 bathrooms
2–7 Aug
4.98 out of 5 average rating, 120 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
Meadowland Farmhouse — 5 minutes from town
3 bedrooms, 5 beds, 2 bathrooms
15–20 Jul
5.0 out of 5 average rating, 21 reviews
Superhost
Home in Town of Hillsdale
Quaint center of town Farmhouse
2 bedrooms, 3 beds, 1 bathroom
13–18 Jul
Top guest favourite
Home in Copake Lake
Waterside Private Retreat Home Near Copake Lake
3 bedrooms, 5 beds, 2 bathrooms
24–29 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Salisbury
Greystone at Twin Lakes
3 bedrooms, 3 beds, 1 bathroom
24–29 Aug
4.99 out of 5 average rating, 67 reviews
Guest favourite
Home in Town of Hillsdale
Serene Hillsdale Cottage Amped with Tech and Wifi
4 bedrooms, 6 beds, 2.5 bathrooms
13–18 Jul
4.97 out of 5 average rating, 29 reviews
Top guest favourite
Barn in New Marlborough
Hartsville Barn in the Berkshires
2 bedrooms, 2 king beds, 1 bathroom
14–19 Sept
4.98 out of 5 average rating, 41 reviews