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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
Oct 12 - Oct 13
Tomorrow
Oct 13 - Oct 14
This weekend
Oct 16 - Oct 18
Next weekend
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 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 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
Basil
NT$3,384
NT$3,780 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.
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.
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".

2. Berkshires Untold

Berkshires Untold
Lenox
United States
Madhavi R
NT$4,156
NT$4,643 total
includes taxes & fees
Nov 1 - Nov 2
Berkshires Untold
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.

3. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United Kingdom
judith
NT$4,899
NT$5,619 total
includes taxes & fees
Oct 27 - Oct 28
The Cornell Inn, Lenox & The Berkshires
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
Lawrence
NT$4,281
NT$4,782 total
includes taxes & fees
Nov 1 - Nov 2
Hotel On North
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
A modern restaurant with wooden flooring, bar area, and seating arrangements.
A covered outdoor area with stone pillars and a view of a road and green hills.

5. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
United States
Tracy
NT$4,010
NT$4,479 total
includes taxes & fees
Nov 1 - Nov 2
Courtyard by Marriott Lenox Berkshires
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 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
NT$3,735
NT$4,797 total
includes taxes & fees
Oct 22 - Oct 23
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
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 bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.
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$4,083
NT$4,560 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Lenox Pittsfield
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 swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A covered porch with wicker furniture and hanging flower baskets.

8. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Stephan
NT$5,029
NT$7,203 total
includes taxes & fees
Nov 3 - Nov 4
The Red Lion Inn
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.
An outdoor seating area with Adirondack chairs and a fire feature.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.
A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.

9. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
United States
Kirsty
NT$4,565
NT$5,100 total
includes taxes & fees
Nov 8 - Nov 9
Element by Marriott Lenox Berkshires
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.
An outdoor seating area with stone fire pit, chairs, and a red building in the background.
A bar area with wooden beams, red chairs, and a long wooden table.

10. The Williams Inn

The Williams Inn
Williamstown
United States
Soleil
NT$6,486
NT$7,245 total
includes taxes & fees
Nov 8 - Nov 9
The Williams Inn
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Top The Berkshires Hotel Reviews

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"It's a perfect stop on our little Berkshires trip. The Inn had everything we needed and more. The property was beautiful, and the staff was beyond helpful. We will certainly be back."
Alexandra 1-night trip
Posted 1 hour ago
The Cornell Inn, Lenox & The Berkshires
The Red Lion Inn

The Red Lion Inn

8/10 Good
"We had a nice stay at the Red Lion Inn. Our room was clean and had a fireplace, but did not have a mini-refrigerator and the TV was placed to the side of the bed. The restaurant charged a lot ($65 for a filet mignon entree) and the food was not up to that price. The bread and salad were a la carte. The whole place seemed in need of a refresh."
Patricia 1-night trip
Posted 1 hour ago
The Red Lion Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"It's like home away from home."
Teena 2-night trip
Posted 4 hours ago
Vacation Village in the Berkshires
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"It was good"
Vishva 1-night trip
Posted 19 hours ago
Hampton Inn & Suites Berkshires-Lenox
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"First, this is an absolutely gorgeous place! The outside areas are beautiful with comfy furniture, flowers and fire pits. Inside is a small intimate restaurant and bar, plus sitting area. With books and plants, very nice. We had dinner there which was excellent, and loved cocktails and sunset outside by the fire pits. When we checked in, we were assigned one of their premium rooms, which sounded great. However, it was on the second floor, at the very end of a long outside corridor, accessible only by stairs near the lobby. There is no elevator. We did go to the room, lugging our bags and a cooler. Unpleasant, as we are somewhat older. We concluded that we did not want to be that far from the main area, so asked to be moved, and were accommodated. We found the new room the same, but lacking a luggage rack and a coffee service (those were only available in the premium rooms at the end of the long corridor). We were given a luggage rack, and complimentary coffee was available in the restaurant in the morning, but it seemed odd that those were considered premium in such a nice place. Otherwise we loved the hotel, room was very nice with a comfortable bed and a very updated bath with a walk in shower. The real star of the hotel is the lobby restaurant and outdoor space - that was just perfect!"
William 1-night trip
Posted 23 hours ago
Quality Inn Great Barrington
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Our room was nice and clean. The suite is perfect. Can fix a cup of tea or a meal, everything you need just bring your food. A restaurant on site if you don't want to cook. Bed was comfortable with crisp white linens."
Anna 2-night trip
Posted 1 day ago
Jiminy Peak Mountain Resort

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