The Best Hotels with Bars in The Berkshires, MA from ₩138,892 in 2026

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Our top choices for The Berkshires hotels with a bar

Superior Room, 1 King Bed, Jetted Tub | Jetted tub

The Yankee Inn

Lenox

Mark

₩233,584 total

includes taxes & fees

Jun 7 - Jun 8

Berkshires Untold

Lenox

Vivian

₩209,836 total

includes taxes & fees

Jun 3 - Jun 4

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

South Lee

Kimberly

₩239,642 total

includes taxes & fees

Jun 9 - Jun 10

The Red Lion Inn

Stockbridge

molly

₩353,072 total

includes taxes & fees

Jun 9 - Jun 10

Hotel On North

Pittsfield

KEITH AND SHIRLEY

₩300,808 total

includes taxes & fees

Jun 4 - Jun 5

Courtyard by Marriott Lenox Berkshires

Lenox

Phyllis

₩316,102 total

includes taxes & fees

Jun 4 - Jun 5

Cozy Corner Motel

Williamstown

Barbara J

₩149,755 total

includes taxes & fees

Jun 8 - Jun 9

The Cornell Inn, Lenox & The Berkshires

Lenox

Arthur

₩269,467 total

includes taxes & fees

Jun 9 - Jun 10

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Top The Berkshires Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

6/10 Okay

"The staff were very polite and helpful. But the property was under construction, so you had to walk over a block to your car and park it or you can do a valet that was never present? From what I was told from other people that were staying there is that the place I’ve been under construction for a couple years now that was not advertise that was going on so it was kind of frustrating."

Vacation Village in the Berkshires

10/10 Excellent

"I can't say enough about this property. The rooms (our two bedroom suite was actually two conjoined rooms) were bigger and better appointed than advertised. The staff was friendly, helpful and the service was prompt. Everything was included for a family stay including coffee and coffee maker, pots and pans, dishes, glasses and utensils. rTwo things stand out above the great rooms and lovely property. First, my grandchildren locked a toy in the safe and the staff member who recovered the toy was quick, kind, and ever so pleasant. Second, my daughter left a pair of earbuds behind and the staff found them after she left, and the hotel returned them. I'll go out of my way to stay here again and I suggest that you stay here as well."