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Find Hotels with Bars in The Berkshires, MA

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Check availability on The Berkshires Hotels with Bars

Tonight
Sep 12 - Sep 13
Tomorrow
Sep 13 - Sep 14
Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27

Our top choices for The Berkshires hotels with a bar

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.

1. The Yankee Inn

The Yankee Inn
Lenox
United States
Karen
NT$3,671
NT$4,100 total
includes taxes & fees
Sep 22 - Sep 23
The Yankee Inn
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.
An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".
A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.
A cozy library with bookshelves, a fireplace, and comfortable seating.

2. Berkshires Untold

Berkshires Untold
Lenox
United States
David
NT$4,154
NT$4,640 total
includes taxes & fees
Sep 13 - Sep 14
Berkshires Untold
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A bar with wooden floors and shelves filled with bottles.
A covered porch with wicker furniture and hanging flower baskets.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

3. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
James
NT$5,096
NT$7,264 total
includes taxes & fees
Sep 23 - Sep 24
The Red Lion Inn
A building entrance with a large planter with purple flowers and a small tree.
A library with bookshelves, a television, and two armchairs.
A lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.
A restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.

4. Hotel On North

Hotel On North
Pittsfield
United States
Drew
NT$4,236
NT$4,731 total
includes taxes & fees
Sep 13 - Sep 14
Hotel On North
A building with a porch and multiple windows, surrounded by purple flowers.
A café with a display case, a frozen food section, and a marketplace sign.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
A living room with a sofa, armchair, coffee table, and a patterned rug.

5. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
United States
Linda
NT$3,691
NT$4,740 total
includes taxes & fees
Sep 14 - Sep 15
Holiday Inn Club Vacations Oak 'n Spruce Resort
A snow-covered outdoor area with a patio, seating, and a covered dining area.
A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.
A modern living room with a fireplace, comfortable seating, and a large window with curtains.
A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.

6. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United States
Sarah
NT$5,190
NT$5,953 total
includes taxes & fees
Sep 14 - Sep 15
The Cornell Inn, Lenox & The Berkshires
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.
A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.
A spacious living room with a large sofa, a coffee table, and a fireplace.
A hotel patio with outdoor seating and a fire pit.

7. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
United States
James
NT$4,760
NT$5,317 total
includes taxes & fees
Sep 20 - Sep 21
Hilton Garden Inn Lenox Pittsfield
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
A modern restaurant with wooden flooring, bar area, and seating arrangements.
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
A covered outdoor area with stone pillars and a view of a road and green hills.

8. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
United States
Tracy
NT$6,183
NT$6,907 total
includes taxes & fees
Sep 20 - Sep 21
Courtyard by Marriott Lenox Berkshires
A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.
A buffet area with a counter, food items, and a beverage station.
A round dining table set for a formal event, with white tablecloth, silverware, and purple napkins.

9. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
United States
Debra
NT$3,639
NT$4,065 total
includes taxes & fees
Oct 12 - Oct 13
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.
A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.
A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.
An outdoor seating area with Adirondack chairs and a fire feature.

10. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
United States
Kirsty
NT$5,616
NT$6,273 total
includes taxes & fees
Sep 20 - Sep 21
Element by Marriott Lenox Berkshires
View all properties

Top The Berkshires Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"It was very nice. Don’t like how they hold on your credit card 150 as long as they do. I can understand why they do it but I been back a week and there still holding that on my card."
Sandy 1-night trip
Posted 5 hours ago
Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Nasically a large motel with both an outdoor and indoor pool. A bit tired, but reasonably close to Lenox and to Tabglewood."
Jacob 1-night trip
Posted 9 hours ago
The Yankee Inn
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"Great and helpful staff. Delicious complimentary drinks and a free bottle of wine in your room!!"
Sarah 1-night trip
Posted 17 hours ago
The Cornell Inn, Lenox & The Berkshires
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good
"Great location for Mass Moca"
BONNIE 3-night trip
Posted 2 days ago
Hotel Downstreet, an Ascend Collection Hotel
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

8/10 Good
"Clean, staff was great, and ample parking"
Michael 3-night trip
Posted 2 days ago
Best Western Plus Berkshire Hills Inn & Suites
Willows Motel Williamstown

Willows Motel Williamstown

10/10 Excellent
"Awesome staff plus pet-friendly."
Gina 1-night trip
Posted 3 days ago
Willows Motel Williamstown
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"My family had a wonderful time at Jiminy Peak Mountain Resort! The staff truly cared about making sure we had a great stay. When we had a last-minute change and needed to upgrade our room, they handled everything so seamlessly and were incredibly accommodating. The space we received was much larger than we expected, with four floors, three bedrooms, two bathrooms, and three pull-out sofas. There was more than enough room for our whole family to stay comfortably, and it was very affordable for the amount of space and amenities we received. They were also very generous with towels and blankets. Although we didn’t end up using everything, it was reassuring to know that plenty was available if we needed more. The view from the backyard was beautiful, and the resort attractions were only minutes away. We especially enjoyed the scenic chairlift ride and mountain coaster. Everyone in our family, from old to young, had a great time. Overall, it was a wonderful and very affordable family getaway. We really appreciated the hospitality, spacious accommodations, beautiful surroundings, and activities for all ages. We would definitely recommend Jiminy Peak Mountain Resort!"
sophia 1-night trip
Posted 4 days ago
Jiminy Peak Mountain Resort
Hotel On North

Hotel On North

10/10 Excellent
"Best place in town"
Mary Ellen 2-night trip
Posted 5 days ago
Hotel On North

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