Hotels with a Bar in The Berkshires
Massachusetts
United States of America
Hotels with a Bar
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A large white building with multiple chimneys, surrounded by lush gardens with various flowers.

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your current months are November, 2026 and December, 2026.

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Our top choices for The Berkshires hotels with a bar

Two Adirondack chairs facing a river with a forested hill in the background.

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

A hotel room with a fireplace, a desk, a television, and a poster of a lake scene.

1. The Yankee Inn

The Yankee Inn

2.5 star property

Lenox

9.2 out of 10, Wonderful, (1,013 reviews)

9.2/10

Wonderful

(1,013 reviews)

"The location was good for our trip."

Basil

The price is ₹11,311

₹11,311

₹12,634 total

includes taxes & fees

20 Nov - 21 Nov

The Yankee Inn

A multi-story hotel with a classic facade, large windows, and a prominent entrance.

A lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.

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.

2. Hotel On North

Hotel On North

3.5 star property

Pittsfield

9.6 out of 10, Exceptional, (978 reviews)

9.6/10

Exceptional

(978 reviews)

"Very nice hotel"

Philip

The price is ₹11,000

₹11,000

₹12,287 total

includes taxes & fees

29 Nov - 30 Nov

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.

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.

An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".

3. Berkshires Untold

Berkshires Untold

3.5 star property

Lenox

9.0 out of 10, Wonderful, (1,066 reviews)

9.0/10

Wonderful

(1,066 reviews)

"Very nice place beautiful view"

Brian

The price is ₹11,559

₹11,559

₹12,912 total

includes taxes & fees

29 Nov - 30 Nov

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 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.

4. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 star property

Lenox

9.4 out of 10, Exceptional, (1,001 reviews)

9.4/10

Exceptional

(1,001 reviews)

"Lovely room, comfortable bed and a nice breakfast."

judith

The price is ₹16,092

₹16,092

₹18,457 total

includes taxes & fees

10 Nov - 11 Nov

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.

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.

5. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3.0 star property

Lenox

9.2 out of 10, Wonderful, (685 reviews)

9.2/10

Wonderful

(685 reviews)

"Great stay!"

Vandhana

The price is ₹11,901

₹11,901

₹13,293 total

includes taxes & fees

15 Nov - 16 Nov

Courtyard by Marriott Lenox Berkshires

A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

A multi-story building with a symmetrical facade, multiple balconies, and a central tower.

A multi-story building with a balcony, a pond with rocks, and a tree.

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

3.5 star property

South Lee

9.2 out of 10, Wonderful, (1,000 reviews)

9.2/10

Wonderful

(1,000 reviews)

"Nice place to stay"

Michael

The price is ₹11,074

₹11,074

₹14,220 total

includes taxes & fees

10 Nov - 11 Nov

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

A hotel patio with outdoor seating and a fire pit.

A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

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.

7. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

3.0 star property

Pittsfield

9.2 out of 10, Wonderful, (716 reviews)

9.2/10

Wonderful

(716 reviews)

"Great place to stay. Great staff and convenient location. Nice restaurant as well."

James

The price is ₹11,244

₹11,244

₹12,560 total

includes taxes & fees

15 Nov - 16 Nov

Hilton Garden Inn Lenox Pittsfield

A straw hat, sunglasses, and two drinks on a striped towel by a body of water.

A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

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.

8. The Red Lion Inn

The Red Lion Inn

3.5 star property

Stockbridge

8.8 out of 10, Excellent, (1,006 reviews)

8.8/10

Excellent

(1,006 reviews)

"Enjoyed staying in the old hotel and loved the large porch with the bar to relax on."

Mallory

The price is ₹14,924

₹14,924

₹21,378 total

includes taxes & fees

12 Nov - 13 Nov

The Red Lion Inn

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.

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.

9. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires

3.0 star property

Lenox

9.6 out of 10, Exceptional, (51 reviews)

9.6/10

Exceptional

(51 reviews)

"Clean, spacious room Accommodating staff especially Shawn and Jennifer at the front desk. Very nice pool and gym Definitely coming back"

Francis

The price is ₹12,791

₹12,791

₹14,287 total

includes taxes & fees

12 Nov - 13 Nov

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.

An outdoor seating area with stone fire pit, chairs, and a red building in the background.

A spacious interior with a wooden staircase, a seating area with patterned cushions, and large windows allowing natural light.

A spacious living area with a fireplace, wooden beams, and a large window.

10. The Williams Inn

The Williams Inn

4.0 star property

Williamstown

9.6 out of 10, Exceptional, (711 reviews)

9.6/10

Exceptional

(711 reviews)

"Fantastic hotel! Would definitely stay again."

Pete

The price is ₹18,934

₹18,934

₹21,149 total

includes taxes & fees

8 Nov - 9 Nov

The Williams Inn

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

View all properties

Top The Berkshires Hotel Reviews

A bedroom with a large bed, a chair, and a window with curtains.

A large, two-story house with a porch and multiple windows, surrounded by a well-maintained lawn.

A dining area with yellow chairs and tables, a kitchen in the background, and a clock on the wall.

A covered porch with a dining area, a sofa, and decorative wall art.

The White Hart

Salisbury

10/10 Excellent

Everything was excellent. The area, the food, the room, the very comfortable bed and the staff.

liz

Reviewed June 25, 2018Reviewed June 25, 2018

The White Hart

A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

A dining table set with a vase of flowers, a book, and cutlery.

A cozy living room with a fireplace, a blue sofa, a red armchair, and a coffee table with books and a teapot.

A loft bedroom with a sloped ceiling, a ceiling fan, a floor lamp, a bed with a patterned bedspread, a chair, and a small table.

Brook Farm Inn

Lenox

10/10 Excellent

Beautifully presented bed and breakfast accommodation where we felt very much at home. The room was bright and cheerful and outstandingly clean. The water was hot and plentiful and the beds comfortable. Breakfast was freshly cooked and varied and the welcome was warm and informative.

Judy

Reviewed October 13, 2016Reviewed October 13, 2016

Brook Farm Inn

A bedroom with a double bed, two chairs, a small table with a hat, and floral curtains.

A large, two-story house with a covered porch and multiple chimneys.

A stone gate with a lantern, surrounded by trees and a grassy area.

A cozy living room with a fireplace, comfortable seating, and a view of the outdoors.

The Four Chimneys Inn

Bennington

10/10 Excellent

Lovely place very comfortable

Hannah

Reviewed July 3, 2026Reviewed July 3, 2026

The Four Chimneys Inn

The Cornell Inn, Lenox & The Berkshires

Lenox

10/10 Excellent

Lovely room, comfortable bed and a nice breakfast.

judith

Reviewed October 10, 2026Reviewed October 10, 2026

The Cornell Inn, Lenox & The Berkshires

A large, historic building with a covered porch and outdoor seating area.

A grand staircase with patterned carpet, a wooden table with a vase of flowers, a chandelier, and a clock.

A large, historic house with multiple chimneys, a covered porch, and lush greenery.

A grand foyer with a patterned carpet, a wooden staircase, a chandelier, a mounted deer head, and a large clock.

Simsbury 1820 House

Simsbury Center

10/10 Excellent

Superb room with 4 poster, lovely owner and excellent value for money

Tim & Angela

Reviewed April 30, 2015Reviewed April 30, 2015

Simsbury 1820 House

Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.

A row of colorful Victorian-style houses with a prominent red one labeled "PORCHES."

A hallway with a collection of plates on the walls, leading to a staircase.

Two people sitting by a campfire in a wooded area with benches and a clear view of the surrounding trees.

The Porches Inn at Mass MoCA

North Adams

10/10 Excellent

Nice stay with friendly welcoming staff

Martin

Reviewed May 11, 2019Reviewed May 11, 2019

The Porches Inn at Mass MoCA

The Yankee Inn

Lenox

10/10 Excellent

Excellent room. All very clean.

Martin

Reviewed October 15, 2025Reviewed October 15, 2025

The Yankee Inn

Courtyard by Marriott Lenox Berkshires

Lenox

10/10 Excellent

Helpful staff, clean room and great facilities.

Laura

Reviewed July 30, 2026Reviewed July 30, 2026

Courtyard by Marriott Lenox Berkshires

Hilton Garden Inn Lenox Pittsfield

Pittsfield

8/10 Good

The most unfriendly front desk staff on arrival out of the 6 hotels we've stayed in this vacation. Hotel is very modern but with questionable decorative style (i.e. Gaudy colour scheme and patterned carpets). Rooms are spacious and well equipped. Restaurant is a bit soulless but colleague working the bar, taking food orders, doing room service (ie. Everything!) is a bit of a star.

Anonymous traveller

Reviewed October 14, 2016Reviewed October 14, 2016

Hilton Garden Inn Lenox Pittsfield

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

South Lee

10/10 Excellent

We absolutely loved it here 10/10

Judith

Reviewed August 8, 2026Reviewed August 8, 2026

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

A patio area with wooden chairs and tables, surrounded by dense greenery and trees.

A white two-story building with a porch, labeled as a motel.

A hay bale display with pumpkins and scarecrows.

A hotel room with a TV, a desk, a chair, a dresser, a bed with a patterned bedspread, and a microwave.

Willows Motel Williamstown

Williamstown

10/10 Excellent

On Mohawk Trail. Limited space to eat if raining, but excellent choice for breakfast

Russell

Reviewed October 18, 2018Reviewed October 18, 2018

Willows Motel Williamstown

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Search Hotels with a Bar in The Berkshires

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for The Berkshires hotels with a bar

1. The Yankee Inn

2. Hotel On North

3. Berkshires Untold

4. The Cornell Inn, Lenox & The Berkshires

5. Courtyard by Marriott Lenox Berkshires

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

7. Hilton Garden Inn Lenox Pittsfield

8. The Red Lion Inn

9. Element by Marriott Lenox Berkshires

10. The Williams Inn

Top The Berkshires Hotel Reviews

The White Hart

10/10 Excellent

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