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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 14 - Sep 15
Tomorrow
Sep 15 - Sep 16
This weekend
Sep 18 - Sep 20
Next weekend
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 cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.

1. The Yankee Inn

The Yankee Inn
Lenox
United States
Robert
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.
A cozy library with bookshelves, a fireplace, and comfortable seating.
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.

2. Berkshires Untold

Berkshires Untold
Lenox
United States
Drue
NT$4,166
NT$4,653 total
includes taxes & fees
Sep 16 - Sep 17
Berkshires Untold
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A backyard with a swimming pool, lounge chairs, and a hot tub.
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.

3. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
James
NT$5,012
NT$7,171 total
includes taxes & fees
Sep 28 - Sep 29
The Red Lion Inn
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 living room with a sofa, armchair, coffee table, and a patterned rug.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

4. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
United States
Linda
NT$3,702
NT$4,754 total
includes taxes & fees
Sep 21 - Sep 22
Holiday Inn Club Vacations Oak 'n Spruce Resort
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 lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.

5. Hotel On North

Hotel On North
Pittsfield
United States
Drew
NT$4,248
NT$4,745 total
includes taxes & fees
Sep 15 - Sep 16
Hotel On North
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.
A spacious living room with a large sofa, a coffee table, and a fireplace.
A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.

6. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
United States
James
NT$4,629
NT$5,171 total
includes taxes & fees
Sep 20 - Sep 21
Hilton Garden Inn Lenox Pittsfield
A snow-covered outdoor area with a patio, seating, and a covered dining area.
A modern living room with a fireplace, comfortable seating, and a large window with curtains.
A dining area with a glass table, red walls, and framed artwork.
A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.

7. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United States
Rosann
NT$6,428
NT$7,373 total
includes taxes & fees
Sep 15 - Sep 16
The Cornell Inn, Lenox & The Berkshires
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.
A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.

8. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
United States
Tracy
NT$6,202
NT$6,927 total
includes taxes & fees
Sep 20 - Sep 21
Courtyard by Marriott Lenox Berkshires
A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.
A round dining table set for a formal event, with white tablecloth, silverware, and purple napkins.
A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.

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 hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.
A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.
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$5,633
NT$6,292 total
includes taxes & fees
Sep 24 - Sep 25
Element by Marriott Lenox Berkshires
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Top The Berkshires Hotel Reviews

Hotel On North

Hotel On North

10/10 Excellent
"Great location, clean room!"
Gayle 1-night trip
Posted 6 hours ago
Hotel On North
The Red Lion Inn

The Red Lion Inn

8/10 Good
"We stopped at the red lion Inn on our travels back home from Maine. Our room was a block away from the main building and in an old house. It was very clean and comfortable. The location in town is nice."
Guy 1-night trip
Posted 10 hours ago
The Red Lion Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"It was perfect for our weekend away, clean, comfortable bed and a decent breakfast, definitely worth the value:)"
Kimberly 2-night trip
Posted 1 day ago
Quality Inn Great Barrington
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Loved the pond trail! What a nice shift after a long day on the road."
Deborah 1-night trip
Posted 1 day ago
The Yankee Inn
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good
"Clean room, great location. Perfect base for a weekend in the Berkshires."
Alexandra 2-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 4 days ago
Best Western Plus Berkshire Hills Inn & Suites

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