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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
9–14 Aug
4.94 out of 5 average rating, 95 reviews
Place to stay in Town of Hillsdale
Bellwether on Main, Passive House & AAC
2 bedrooms, 2 queen beds
21–26 Jul
Top guest favourite
Flat in Town of Hillsdale
Serene Suite: Hudson & Berkshires, Walk to Brewery
1 bedroom, 1 queen bed
9–14 Aug
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
18–23 Jul
5.0 out of 5 average rating, 37 reviews
Guest favourite
Cabin in Town of Hillsdale
Tory Hill Cabin; (North Mountain Cottages)
3 bedrooms, 3 beds
13–18 Sept
4.9 out of 5 average rating, 178 reviews
Top guest favourite
Home in Town of Hillsdale
Gorgeous Mountain Views Retreat: Family & Nature
4 bedrooms, 5 beds
26–31 Jul
4.97 out of 5 average rating, 78 reviews
Guest favourite
Guest suite in Town of Hillsdale
Overnight at Althouse-Higgins
2 bedrooms, 3 beds
19–24 Jul
4.98 out of 5 average rating, 142 reviews
Guest favourite
Home in Copake
Modern Rustic Getaway | Quiet | Wifi |Parking
3 bedrooms, 3 beds
3–8 Aug
4.97 out of 5 average rating, 76 reviews
Superhost
Home in Town of Hillsdale
Quaint center of town Farmhouse
2 bedrooms, 3 beds
15–20 Jul
Top guest favourite
Home in Town of Hillsdale
Meadowland Farmhouse — 5 minutes from town
3 bedrooms, 5 beds
17–22 Jul
5.0 out of 5 average rating, 22 reviews
Guest favourite
Home in Town of Hillsdale
Historic 1850s "The Bell House" with Private Pool
5 bedrooms, 5 beds
12–17 Oct
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Salisbury
Greystone at Twin Lakes
3 bedrooms, 3 beds
24–29 Aug
4.99 out of 5 average rating, 67 reviews
Top guest favourite
Loft in Great Barrington
The Old Red Barn
1 bedroom, 1 queen bed
1–6 Sept
4.99 out of 5 average rating, 364 reviews
Guest favourite
Home in Copake
Copake Retreat
3 bedrooms, 4 beds
27 Jul – 1 Aug
4.9 out of 5 average rating, 139 reviews
Top guest favourite
Home in Copake Lake
Waterside Private Retreat Home Near Copake Lake
3 bedrooms, 5 beds
3–8 Aug
5.0 out of 5 average rating, 14 reviews
Guest favourite
Cabin in Town of Ancram
Architectural Cabin, 2 bed, near Taghkanic Lake
1 bedroom, 2 queen beds
27 Jul – 1 Aug
4.98 out of 5 average rating, 48 reviews
Guest favourite
Home in Chatham
Writer's Retreat in the Woods
2 bedrooms, 2 queen beds
27 Mar – 1 Apr
5.0 out of 5 average rating, 39 reviews
Top guest favourite
Home in Copake
Bright/Spacious Getaway at foot of the Berkshires
4 bedrooms, 4 queen beds
30 Jul – 4 Aug
4.95 out of 5 average rating, 104 reviews