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Search results; Over 1,000 homes in Hillsdale

Top guest favourite
Flat in Town of Hillsdale
Serene Suite: Hudson & Berkshires, Walk to Brewery
1 bedroom, 1 bed, 1 private bathroom
9–14 Aug
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4.98 out of 5 average rating, 249 reviews
Top guest favourite
Place to stay in Town of Hillsdale
Sun Filled Historic Retreat | Berkshires & Hudson
1 bedroom, 1 queen bed, 1 bathroom
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, 2 bathrooms
21–26 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
Home in Town of Hillsdale
Private unit in shared 1830 Farmhouse
2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
5.0 out of 5 average rating, 38 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
Barn in Town of Hillsdale
Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna
3 bedrooms, 3 beds, 2 bathrooms
12–17 Aug
4.97 out of 5 average rating, 178 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, 14 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, 78 reviews
Guest favourite
Home in Copake
Copake Retreat
3 bedrooms, 4 beds, 2 bathrooms
27 Jul – 1 Aug
4.92 out of 5 average rating, 139 reviews
Guest favourite
Guest suite in Town of Hillsdale
Overnight at Althouse-Higgins
2 bedrooms, 3 beds, 1 bathroom
26–31 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 Copake Lake
Waterside Private Retreat Home Near Copake Lake
3 bedrooms, 5 beds, 2 bathrooms
31 Jul – 5 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Cabin in Town of Taghkanic
A Summer Reset. Rest. Reconnect. Upstate.
2 bedrooms, 2 beds, 1 bathroom
27 Aug – 1 Sept
4.95 out of 5 average rating, 41 reviews
Top guest favourite
Home in Town of Ancram
Near Hudson-Gorgeous Sunsets+Catskill Mt Views
3 bedrooms, 3 queen beds, 2 bathrooms
23–28 Jul
5.0 out of 5 average rating, 40 reviews
Guest favourite
Home in Copake
Modern Rustic Getaway | Quiet | Wifi |Parking
3 bedrooms, 3 beds, 2 bathrooms
17–22 Aug
4.97 out of 5 average rating, 77 reviews
Top guest favourite
Home in Town of Hillsdale
Meadowland Farmhouse — 5 minutes from town
3 bedrooms, 5 beds, 2 bathrooms
24–29 Aug
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Cottage in Great Barrington
Artist Cottage
1 bedroom, 1 queen bed, 2 bathrooms
2–7 Aug
4.93 out of 5 average rating, 345 reviews