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Search results; Over 1,000 homes in Hillsdale

Top guest favourite
Cottage in Town of Hillsdale
Underhill Cottage
3 bedrooms, 3 beds, 2 shared bathrooms
28 Sept – 3 Oct
,
4.98 out of 5 average rating, 59 reviews
Guest favourite
Rooms in Town of Hillsdale
Bellwether on Main, Passive House & AAC
2 bedrooms, 2 queen beds
23–28 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
23–28 Aug
4.98 out of 5 average rating, 258 reviews
Guest favourite
Home in Town of Hillsdale
Historic 1850s "The Bell House" with Private Pool
5 bedrooms, 5 beds
26–31 Oct
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Place to stay in Town of Hillsdale
Sun Filled Historic Retreat | Berkshires & Hudson
1 bedroom, 1 queen bed
23–28 Aug
4.94 out of 5 average rating, 102 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
Guest suite in Town of Hillsdale
The Barn @ Althouse - Higgins
2 bedrooms, 3 beds
22–27 Aug
5.0 out of 5 average rating, 29 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, 81 reviews
Top guest favourite
Home in Town of Hillsdale
Private unit in shared 1830 Farmhouse
2 bedrooms, 2 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 41 reviews
Top guest favourite
Barn in Town of Hillsdale
Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna
3 bedrooms, 3 beds
7–12 Sept
4.97 out of 5 average rating, 181 reviews
Superhost
Home in Town of Hillsdale
Quaint center of town Farmhouse
2 bedrooms, 3 beds
19–24 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Barn in Town of Ancram
Serene Modern Barn near Hudson
3 bedrooms, 3 beds
24–29 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
28 Aug – 2 Sept
4.98 out of 5 average rating, 122 reviews
Superhost
Barn in Town of Hillsdale
Historic 1850s Carriage House Studio @ Town Center
1 bedroom, 1 queen bed
22–27 Aug
4.88 out of 5 average rating, 17 reviews
Home in Great Barrington
Garden Retreat, 1st fl KING ste, EV, close to all
3 bedrooms, 4 beds
23–28 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Cabin in Town of Hillsdale
Cabin in the woods near Catamount Ski resort
2 bedrooms, 3 beds
15–20 Sept
4.88 out of 5 average rating, 187 reviews
Top guest favourite
Cabin in Mount Washington
Chic Cabin in the Berkshires, Mountain getaway!
4 bedrooms, 6 beds
15–20 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Austerlitz
Private cottage close to shopping, dining, skiing.
3 bedrooms, 4 beds
23–28 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Guest house in Athens
Athens Cottage
2 bedrooms, 3 beds
4–9 Nov
4.97 out of 5 average rating, 75 reviews