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Search results; Over 1,000 homes in Hillsdale

Guest favourite

Cabin in Town of Hillsdale

Cabin in the woods near Catamount Ski resort

2 bedrooms, 3 beds, 2 private bathrooms

31 Aug – 5 Sept

$1,842 SGD for 5 nights

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4.88 out of 5 average rating, 186 reviews

Rooms in Town of Hillsdale

Bellwether on Main, Passive House & AAC

2 bedrooms, 2 queen beds

2–7 Aug

$1,334 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Top guest favourite

Flat in Town of Hillsdale

Serene Suite: Hudson & Berkshires, Walk to Brewery

1 bedroom, 1 queen bed

9–14 Aug

$830 SGD for 5 nights

4.98 out of 5 average rating, 253 reviews

Top guest favourite

Place to stay in Town of Hillsdale

Sun Filled Historic Retreat | Berkshires & Hudson

1 bedroom, 1 queen bed

9–14 Aug

$813 SGD for 5 nights

4.94 out of 5 average rating, 98 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, 16 reviews

Home in Town of Hillsdale

Secluded 19-Acre Hudson Valley Escape w/ Pool

3 bedrooms, 6 beds

16–21 Aug

$5,864 SGD for 5 nights

New place to stay

Top guest favourite

Home in Town of Hillsdale

Private unit in shared 1830 Farmhouse

2 bedrooms, 2 beds

12–17 Aug

$1,743 SGD for 5 nights

5.0 out of 5 average rating, 39 reviews

Guest favourite

Cabin in Town of Hillsdale

Secluded Mountain Getaway with Swimming Pond.

4 bedrooms, 4 queen beds

13–18 Sept

$1,975 SGD for 5 nights

4.91 out of 5 average rating, 128 reviews

Guest favourite

Guest suite in Town of Hillsdale

Overnight at Althouse-Higgins

2 bedrooms, 3 beds

1–6 Aug

$1,798 SGD for 5 nights

4.98 out of 5 average rating, 143 reviews

Top guest favourite

Barn in Town of Hillsdale

Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna

3 bedrooms, 3 beds

12–17 Aug

$7,029 SGD for 5 nights

4.97 out of 5 average rating, 179 reviews

Superhost

Home in Town of Hillsdale

Quaint center of town Farmhouse

2 bedrooms, 3 beds

1–6 Aug

$2,515 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Guest favourite

Home in Town of Hillsdale

Berkshire Mountain House

4 bedrooms, 8 beds

31 Aug – 5 Sept

$2,925 SGD for 5 nights

4.94 out of 5 average rating, 34 reviews

Guest favourite

Cottage in Craryville

Farm Cottage w/ Donkeys, Fire Pit & Wood Stove

3 bedrooms, 3 double beds

2–7 Aug

$1,458 SGD for 5 nights

4.91 out of 5 average rating, 594 reviews

Top guest favourite

Home in Town of Hillsdale

Gorgeous Mountain Views Retreat: Family & Nature

4 bedrooms, 5 beds

13–18 Aug

4.98 out of 5 average rating, 80 reviews

Top guest favourite

Barn in Town of Hillsdale

Blue Door Barn - Pond and Sweeping Views

1 bedroom, 2 beds

17–22 Aug

$1,845 SGD for 5 nights

5.0 out of 5 average rating, 11 reviews

Top guest favourite

Loft in Great Barrington

The Old Red Barn

1 bedroom, 1 queen bed

10–15 Aug

$1,444 SGD for 5 nights

4.99 out of 5 average rating, 365 reviews

Top guest favourite

Cottage in Great Barrington

Artist Cottage

1 bedroom, 1 queen bed

13–18 Sept

$2,089 SGD for 5 nights

4.93 out of 5 average rating, 346 reviews

Guest favourite

Home in Copake

Copake Retreat

3 bedrooms, 4 beds

13–18 Sept

$1,292 SGD for 5 nights

4.92 out of 5 average rating, 140 reviews

Top guest favourite

Cabin in Town of Taghkanic

A Summer Reset. Rest. Reconnect. Upstate.

2 bedrooms, 2 beds

28 Aug – 2 Sept

$1,904 SGD for 5 nights

4.95 out of 5 average rating, 43 reviews