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Search results; Over 1,000 homes in Hillsdale

Chalet in Town of Hillsdale
Natural Splendor: Forest Luxury Retreat
3 bedrooms, 4 beds, 4 private bathrooms
3–8 Oct
,
4.86 out of 5 average rating, 65 reviews
Rooms in Town of Hillsdale
Bellwether on Main, Passive House & AAC
2 bedrooms, 2 queen beds, 2 bathrooms
21–26 Jul
Top guest favourite
Place to stay in Town of Hillsdale
Sun Filled Historic Retreat | Berkshires & Hudson
4.94 out of 5 average rating, 95 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Top guest favourite
Flat in Town of Hillsdale
Serene Suite: Hudson & Berkshires, Walk to Brewery
4.98 out of 5 average rating, 250 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Guest favourite
Cabin in Town of Hillsdale
Tory Hill Cabin; (North Mountain Cottages)
4.9 out of 5 average rating, 178 reviews, 3 bedrooms, 3 beds, 1 bathroom
13–18 Sept
Top guest favourite
Home in Town of Hillsdale
Gorgeous Mountain Views Retreat: Family & Nature
4.97 out of 5 average rating, 78 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
26–31 Jul
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
26–31 Jul
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
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
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
Guest favourite
Guest suite in Town of Hillsdale
Overnight at Althouse-Higgins
4.98 out of 5 average rating, 142 reviews, 2 bedrooms, 3 beds, 1 bathroom
26–31 Jul
Guest favourite
Home in Town of Hillsdale
Historic 1850s "The Bell House" with Private Pool
5.0 out of 5 average rating, 15 reviews, 5 bedrooms, 5 beds, 4.5 bathrooms
19–24 Aug
Superhost
Home in Town of Hillsdale
Quaint center of town Farmhouse
2 bedrooms, 3 beds, 1 bathroom
24–29 Jul
Top guest favourite
Barn in Town of Hillsdale
Blue Door Barn - Pond and Sweeping Views
5.0 out of 5 average rating, 11 reviews, 1 bedroom, 2 beds, 1 bathroom
21–26 Aug
Guest favourite
Home in Copake
Copake Retreat
4.92 out of 5 average rating, 139 reviews, 3 bedrooms, 4 beds, 2 bathrooms
27 Jul – 1 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
Guest favourite
Home in Copake
Modern Rustic Getaway | Quiet | Wifi |Parking
4.97 out of 5 average rating, 77 reviews, 3 bedrooms, 3 beds, 2 bathrooms
17–22 Aug
Superhost
Barn in Town of Hillsdale
Historic 1850s Carriage House Studio @ Town Center
4.88 out of 5 average rating, 16 reviews, 1 bedroom, 1 bed, 1 bathroom
17–22 Aug
Top guest favourite
Cottage in Great Barrington
Artist Cottage
4.93 out of 5 average rating, 346 reviews, 1 bedroom, 1 bed, 2 bathrooms
2–7 Aug