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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
9–14 Sept
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4.97 out of 5 average rating, 185 reviews
Top guest favourite
Flat in Town of Hillsdale
Perfect Apt near Berkshires, Hudson Valley
2 bedrooms, 2 beds
10–17 Sept
4.96 out of 5 average rating, 102 reviews
Top guest favourite
Rooms in Town of Hillsdale
Bellwether on Main, Passive House & AAC
2 bedrooms, 2 queen beds
9–14 Sept
5.0 out of 5 average rating, 11 reviews
Guest favourite
Cabin in Town of Hillsdale
Secluded Mountain Getaway with Swimming Pond.
4 bedrooms, 4 queen beds
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
12–17 Sept
5.0 out of 5 average rating, 43 reviews
Top guest favourite
Home in Town of Hillsdale
Gorgeous Mountain Views Retreat: Family & Nature
4 bedrooms, 5 beds
13–18 Sept
4.98 out of 5 average rating, 83 reviews
Superhost
Barn in Town of Hillsdale
Historic 1850s Carriage House Studio @ Town Center
1 bedroom, 1 queen bed
28 Sept – 3 Oct
4.89 out of 5 average rating, 19 reviews
Top guest favourite
Guest suite in Town of Hillsdale
The Barn @ Althouse - Higgins
2 bedrooms, 3 beds
14–19 Sept
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Place to stay in Town of Hillsdale
Sun Filled Historic Retreat | Berkshires & Hudson
1 bedroom, 1 queen bed
20–25 Sept
4.94 out of 5 average rating, 107 reviews
Top guest favourite
Cottage in Town of Hillsdale
Underhill Cottage
3 bedrooms, 3 beds
28 Sept – 3 Oct
4.98 out of 5 average rating, 59 reviews
Guest favourite
Home in Town of Hillsdale
Berkshire Mountain House
4 bedrooms, 8 beds
11–16 Sept
4.94 out of 5 average rating, 34 reviews
Top guest favourite
Flat in Town of Hillsdale
Serene Suite: Hudson & Berkshires, Walk to Brewery
1 bedroom, 1 queen bed
11–16 Oct
4.98 out of 5 average rating, 262 reviews
Guest favourite
Home in Town of Hillsdale
Modern Lux Estate+Guesthouse, Swimming Pond
6 bedrooms, 6 beds
10–15 Sept
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Home in Town of Hillsdale
Lakefront close to ski & shopping
3 bedrooms, 8 beds
13–18 Sept
5.0 out of 5 average rating, 69 reviews
Top guest favourite
Home in Great Barrington
The Hideaway: Berkshire Home - village of Egremont
3 bedrooms, 7 beds
10–15 Sept
4.95 out of 5 average rating, 148 reviews
Guest favourite
Home in Town of Hillsdale
Lake Front House with Rustic and Charming Feel
3 bedrooms, 4 beds
9–14 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Town of Hillsdale
Serene Hillsdale Cottage Amped with Tech and Wifi
4 bedrooms, 6 beds
9–14 Sept
4.97 out of 5 average rating, 32 reviews
Guest favourite
Home in Great Barrington
Pool & Hot Tub Escape • Hudson Valley-Berkshires
4 bedrooms, 5 beds
25–30 Oct
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Cabin in Town of Taghkanic
A Summer Reset. Rest. Reconnect. Upstate.
2 bedrooms, 2 beds
26–31 Oct
4.96 out of 5 average rating, 47 reviews