A rural landscape with snow-covered fields, a winding road, and scattered trees.

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Check prices for these dates

Tonight
6 Oct - 7 Oct
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7 Oct - 8 Oct
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9 Oct - 11 Oct
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16 Oct - 18 Oct
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Top Hillsdale Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

8/10 Good
"Loved our stay. Room was nice and clean. Some things a little dated but great for the price!"
Lauren 2-night trip
Posted 3 hours ago
Berkshire Mountain Lodge
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"Delightful and charming! When you go to an inn that is over 200 years old you don’t know what to expect and everything was a wonderful surprise. Super clean, stylish, and staff that was warm and friendly. We had what we believe was the smallest room in the Inn, not much over 100 ft.², and it was perfect for a one night stay. The breakfast options were a real treat!"
F. Cole 1-night trip
Posted 7 hours ago
The Cornell Inn, Lenox & The Berkshires
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

8/10 Good
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Alexandra 1-night trip
Posted 20 hours ago
Pocketbook Hotel and Bath
Hotel On North

Hotel On North

10/10 Excellent
"Beautiful boutique hotel. We will be back!"
Rebecca 1-night trip
Posted 22 hours ago
Hotel On North
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good
"I would recommend for families or large groups."
John 2-night trip
Posted 23 hours ago
Holiday Inn Club Vacations Oak 'n Spruce Resort
St. Charles Hotel

St. Charles Hotel

8/10 Good
"The St. Charles hotel is a good place to stay if you are looking for a great location to stay. It's within walking distance of restaurants and close to places to visit. However the WiFi network does kick out a lot."
James 2-night trip
Posted 1 day ago
St. Charles Hotel
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"The staff was very pleasant and helpful. Breakfast was good. They had delicious and fresh muffins. Parking was right outside our door."
Leslie 2-night trip
Posted 1 day ago
Quality Inn Great Barrington
Berkshires Untold

Berkshires Untold

8/10 Good
"Fantastic location, and friendly staff. The rooms were comfortable."
David 1-night trip
Posted 2 days ago
Berkshires Untold
Interlaken Inn & Resort

Interlaken Inn & Resort

10/10 Excellent
"The Interlaken is a lovely property "between the lakes" in Lakeville. We stayed in the main building, which I recommend (there is also another building on the property with a view of the lake). We had a nice screened-in balcony porch attached to our room which we enjoyed each evening. The lobby is cozy with a fireplace. The staff were friendly and helpful."
Suzanne 5-night trip
Posted 5 days ago
Interlaken Inn & Resort