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Hotels with Bars / Lounges in The Berkshires, Massachusetts

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Check availability on The Berkshires Hotels with Bars / Lounges

Tonight
Oct 10 - Oct 11
Tomorrow
Oct 11 - Oct 12
Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25

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 view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
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
Basil
P6,659
P7,438 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee 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 spacious room with a large window, a brick wall, a sofa set, and a patterned carpet.
A restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.

2. Hotel On North

Hotel On North
Pittsfield
United States
Lawrence
P8,424
P9,410 total
includes taxes & fees
Nov 1 - Nov 2
Hotel On North
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.
A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.
An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".
A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.

3. Berkshires Untold

Berkshires Untold
Lenox
United States
Madhavi R
P8,179
P9,136 total
includes taxes & fees
Nov 2 - Nov 3
Berkshires Untold
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
A covered outdoor area with stone pillars and a view of a road and green hills.
A modern restaurant with wooden flooring, bar area, and seating arrangements.
A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

4. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
United States
Tracy
P7,891
P8,814 total
includes taxes & fees
Nov 8 - Nov 9
Courtyard by Marriott Lenox Berkshires
A snow-covered outdoor area with a patio, seating, and a covered dining area.
A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.
A modern living room with a fireplace, comfortable seating, and a large window with curtains.
A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.

5. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United States
Rosann
P9,640
P11,057 total
includes taxes & fees
Oct 27 - Oct 28
The Cornell Inn, Lenox & The Berkshires
A building with a porch and multiple windows, surrounded by purple flowers.
A living room with a sofa, armchair, coffee table, and a patterned rug.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.

6. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
South Lee
United States
Jared
P7,350
P9,438 total
includes taxes & fees
Oct 22 - Oct 23
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
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 brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A covered porch with wicker furniture and hanging flower baskets.

7. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Stephan
P9,896
P14,174 total
includes taxes & fees
Nov 3 - Nov 4
The Red Lion Inn
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.
A spacious living room with a large sofa, a coffee table, and a fireplace.
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.
A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.

8. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
United States
James
P8,034
P8,973 total
includes taxes & fees
Nov 8 - Nov 9
Hilton Garden Inn Lenox Pittsfield
A large, multi-story building with a prominent stone facade and a metal roof, surrounded by landscaped gardens and a pedestrian bridge.
A spacious interior with a wooden staircase, a seating area with patterned cushions, and large windows allowing natural light.
A bar area with wooden beams, red chairs, and a long wooden table.
An outdoor seating area with stone fire pit, chairs, and a red building in the background.

9. The Williams Inn

The Williams Inn
Williamstown
United States
Soleil
P12,762
P14,255 total
includes taxes & fees
Nov 8 - Nov 9
The Williams Inn
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.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.

10. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
United States
Kirsty
P8,983
P10,034 total
includes taxes & fees
Nov 8 - Nov 9
Element by Marriott Lenox Berkshires
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Top The Berkshires Hotel Reviews

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

8/10 Good
"It was fine. No breakfast that I saw"
Michael 1-night trip
Posted 14 hours ago
Best Western Plus Berkshire Hills Inn & Suites
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Although it's an older hotel, it's well maintained.Clean and updated also very friendly staff."
Marti 1-night trip
Posted 19 hours ago
The Yankee Inn
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

8/10 Good
"The pool and hot tub were not heated enough. We didn't plan to use any other amenities so that was a disappointment. We enjoyed our stay. The room was good as we are our breakfast and dinner in the room. The kitchen was great and equipped with everything we needed."
Abby 2-night trip
Posted 20 hours ago
Jiminy Peak Mountain Resort
The Red Lion Inn

The Red Lion Inn

8/10 Good
"Would go there again but would request to be in the main Inn, they have properties all over the town center that are considered the Inn. That was disappointing. A very unique property and super cute!"
Joanne 1-night trip
Posted 4 days ago
The Red Lion Inn
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 5 days ago
Quality Inn Great Barrington

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