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Search results; Over 1,000 homes in Hillsdale

Home in Town of Hillsdale
Fenced yard, playroom & the Berkshires - $0 fees
4 bedrooms, 5 beds, 3 private bathrooms
9–14 Sept
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4.84 out of 5 average rating, 193 reviews
Top guest favourite
Rooms in Town of Hillsdale
Bellwether on Main, Passive House & AAC
2 bedrooms, 2 queen beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Town of Hillsdale
Serene Suite: Hudson & Berkshires, Walk to Brewery
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 258 reviews
Top guest favourite
Place to stay in Town of Hillsdale
Sun Filled Historic Retreat | Berkshires & Hudson
1 bedroom, 1 queen bed, 1 bathroom
6–11 Sept
4.94 out of 5 average rating, 104 reviews
Guest favourite
Home in Town of Hillsdale
Historic 1850s "The Bell House" with Private Pool
5 bedrooms, 5 beds, 4.5 bathrooms
26–31 Oct
5.0 out of 5 average rating, 18 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 Town of Hillsdale
Private unit in shared 1830 Farmhouse
2 bedrooms, 2 beds, 1 bathroom
12–17 Sept
5.0 out of 5 average rating, 41 reviews
Top guest favourite
Home in Town of Hillsdale
Gorgeous Mountain Views Retreat: Family & Nature
4 bedrooms, 5 beds, 2.5 bathrooms
13–18 Sept
4.98 out of 5 average rating, 82 reviews
Top guest favourite
Barn in Town of Hillsdale
Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.97 out of 5 average rating, 182 reviews
Top guest favourite
Guest suite in Town of Hillsdale
The Barn @ Althouse - Higgins
2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 29 reviews
Superhost
Home in Town of Hillsdale
Quaint center of town Farmhouse
2 bedrooms, 3 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 3 reviews
Flat in Egremont
Berkshires Charm Private Apartment
1 bedroom, 1 queen bed, 1 bathroom
18–23 Oct
New place to stay
Top guest favourite
Barn in Town of Hillsdale
Blue Door Barn - Pond and Sweeping Views
1 bedroom, 2 beds, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Town of Taghkanic
Wildflower Cottage near Hudson w/ Fire Pit & AC
3 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Farm stay in Chatham
Cozy, Charming Cabin Studio in Prime Hudson Valley
1 bedroom, 1 king bed, 1 bathroom
27 Sept – 2 Oct
4.99 out of 5 average rating, 80 reviews
Top guest favourite
Barn in New Marlborough
Hartsville Barn in the Berkshires
2 bedrooms, 2 king beds, 1 bathroom
27 Oct – 1 Nov
4.98 out of 5 average rating, 46 reviews
Guest favourite
Home in Town of Hillsdale
Berkshire Mountain House
4 bedrooms, 8 beds, 3 bathrooms
1–6 Sept
4.94 out of 5 average rating, 34 reviews
Guest favourite
Cottage in Egremont
Kayak on Prospect Lake, Paddle Boards, Swim Dock+!
3 bedrooms, 5 beds, 1 bathroom
12–17 Sept
4.98 out of 5 average rating, 55 reviews
Guest favourite
Home in Austerlitz
Private cottage close to shopping, dining, skiing.
3 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 14 reviews