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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 baths
Oct 3 – 8
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4.86 out of 5 average rating, 65 reviews
Top guest favorite
Place to stay in Town of Hillsdale
Sun Filled Historic Retreat | Berkshires & Hudson
1 bedroom, 1 queen bed, 1 bath
Aug 16 – 21
4.94 out of 5 average rating, 101 reviews
Top guest favorite
Apartment in Town of Hillsdale
Serene Suite: Hudson & Berkshires, Walk to Brewery
1 bedroom, 1 queen bed, 1 bath
Aug 23 – 28
4.98 out of 5 average rating, 257 reviews
Guest favorite
Home in Town of Hillsdale
Historic 1850s "The Bell House" with Private Pool
5 bedrooms, 5 beds, 4.5 baths
Oct 26 – 31
5.0 out of 5 average rating, 16 reviews
Top guest favorite
Home in Town of Hillsdale
Private unit in shared 1830 Farmhouse
2 bedrooms, 2 beds, 1 bath
Aug 29 – Sep 3
5.0 out of 5 average rating, 41 reviews
Guest favorite
Rooms in Town of Hillsdale
Bellwether on Main, Passive House & AAC
2 bedrooms, 2 queen beds, 2 baths
Aug 19 – 24
5.0 out of 5 average rating, 6 reviews
Guest favorite
Cabin in Town of Hillsdale
Secluded Mountain Getaway with Swimming Pond.
4 bedrooms, 4 queen beds, 3 baths
Sep 13 – 18
4.91 out of 5 average rating, 128 reviews
Top guest favorite
Barn in Town of Hillsdale
Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna
3 bedrooms, 3 beds, 2 baths
Aug 30 – Sep 4
4.97 out of 5 average rating, 181 reviews
Top guest favorite
Home in Town of Hillsdale
Gorgeous Mountain Views Retreat: Family & Nature
4 bedrooms, 5 beds, 2.5 baths
Sep 13 – 18
4.98 out of 5 average rating, 80 reviews
Top guest favorite
Cottage in Town of Hillsdale
Underhill Cottage
3 bedrooms, 3 beds, 2 baths
Sep 28 – Oct 3
4.98 out of 5 average rating, 59 reviews
Guest favorite
Guest suite in Town of Hillsdale
Overnight at Althouse-Higgins
2 bedrooms, 3 beds, 1 bath
Aug 23 – 28
4.98 out of 5 average rating, 143 reviews
Guest favorite
Farm stay in Town of Hillsdale
FARM HOUSE on Old Horse Farm!
4 bedrooms, 7 beds, 2.5 baths
Aug 13 – 18
4.98 out of 5 average rating, 82 reviews
Superhost
Home in Town of Hillsdale
Quaint center of town Farmhouse
2 bedrooms, 3 beds, 1 bath
Aug 13 – 18
5.0 out of 5 average rating, 3 reviews
Home in Town of Hillsdale
Saltwater Pool - Hudson Valley Escape on 19 acres
3 bedrooms, 6 beds, 2.5 baths
Sep 8 – 13
New place to stay
Guest favorite
Home in Town of Hillsdale
Berkshire Mountain House
4 bedrooms, 8 beds, 3 baths
Aug 31 – Sep 5
4.94 out of 5 average rating, 34 reviews
Guest favorite
Cabin in Town of Hillsdale
Cabin in the woods near Catamount Ski resort
2 bedrooms, 3 beds, 2 baths
Sep 15 – 20
4.88 out of 5 average rating, 187 reviews
Superhost
Barn in Town of Hillsdale
Historic 1850s Carriage House Studio @ Town Center
1 bedroom, 1 queen bed, 1 bath
Aug 22 – 27
4.88 out of 5 average rating, 17 reviews
Top guest favorite
Home in Copake Lake
Waterside Private Retreat Home Near Copake Lake
3 bedrooms, 5 beds, 2 baths
Aug 30 – Sep 4
5.0 out of 5 average rating, 19 reviews
Top guest favorite
Home in Town of Hillsdale
Meadowland Farmhouse — 5 minutes from town
3 bedrooms, 5 beds, 2 baths
Aug 24 – 29
5.0 out of 5 average rating, 23 reviews