The Best Hotels with Bars in The Berkshires, MA from NT$3,853 in 2026

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Our top choices for The Berkshires hotels with a bar

An outdoor patio with a stone table and chairs, a grill, and a stone fireplace.

1. Maya's Garden House

Great Barrington

NT$40,954 total

includes taxes & fees

Nov 1 - Nov 2

A calm lake at dusk with a wooden dock and two chairs facing the water.

2. Berkshire Lake Lodge

Lee

mike

NT$3,926 total

includes taxes & fees

Nov 2 - Nov 3

A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

3. Monument Mountain Motel

Great Barrington

Andrea

NT$2,179 total

includes taxes & fees

Nov 1 - Nov 2

4. Quality Inn Lee - Lenox South

Lee

James

NT$2,999 total

includes taxes & fees

Dec 1 - Dec 2

An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.

5. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

Cynthia

NT$3,022 total

includes taxes & fees

Nov 30 - Dec 1

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

6. The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

Gustavo

NT$3,986 total

includes taxes & fees

Nov 22 - Nov 23

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

7. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

NT$5,222 total

includes taxes & fees

Nov 4 - Nov 5

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

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

South Lee

Michael

NT$4,653 total

includes taxes & fees

Nov 1 - Nov 2

A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

9. East Rock Inn

Great Barrington

Sharon

NT$4,582 total

includes taxes & fees

Dec 1 - Dec 2

A dining area with round tables set for two, a fireplace, and a mural on the wall.

10. The Old Inn On The Green

Great Barrington

mary ellen

NT$11,388 total

includes taxes & fees

Nov 3 - Nov 4

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

11. The Yankee Inn

Lenox

Basil

NT$3,853 total

includes taxes & fees

Nov 1 - Nov 2

A spacious hotel lobby with multiple seating areas, large windows, and a television.

12. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

NT$3,986 total

includes taxes & fees

Nov 6 - Nov 7

13. Berkshire Mountain Lodge

Pittsfield

Charline

NT$3,733 total

includes taxes & fees

Nov 8 - Nov 9

A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

14. Quality Inn Great Barrington

Downtown Great Barrington

Lynne

NT$2,564 total

includes taxes & fees

Dec 1 - Dec 2

An indoor swimming pool with clear water, tiled floors, and a blue wall.

15. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Pittsfield

Yuguo

NT$3,750 total

includes taxes & fees

Nov 30 - Dec 1

A building entrance with a large planter with purple flowers and a small tree.

16. Hotel On North

Pittsfield

Philip

NT$4,220 total

includes taxes & fees

Dec 1 - Dec 2

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

17. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

NT$4,314 total

includes taxes & fees

Nov 15 - Nov 16

A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

18. Element by Marriott Lenox Berkshires

Lenox

Francis

NT$4,907 total

includes taxes & fees

Nov 11 - Nov 12

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

19. Courtyard by Marriott Lenox Berkshires

Lenox

Vandhana

NT$4,135 total

includes taxes & fees

Nov 29 - Nov 30

A two-story building with a sign reading "Chambéry Inn".

20. Chambery Inn

Lee

Alexandra

NT$7,655 total

includes taxes & fees

Nov 1 - Nov 2

View all properties

Top The Berkshires Hotel Reviews

Hotel On North

10/10 Excellent

"What a nice place to stay!"

The Yankee Inn

10/10 Excellent

"The Yankee Inn was clean and on a beautiful property. The beds were extremely comfortable. We enjoyed the morning breakfast, and the staff was extremely kind and helpful. If you book through Expedia - I would call ahead to verify the specifics of the room you have reserved, as Expedia’s description of the room I reserved didn’t match the description on the actual Yankee Inn website. Through Expedia, I reserved a King Deluxe with fireplace, balcony and mountain view. But the actual Yankee Inn website offers EITHER a King Deluxe with a fireplace and balcony OR King Deluxe with mountain view. The management made amends to accommodate as much as possible, but the Expedia advertising was a bit misleading in my opinion."

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Book Hotels with Bars in The Berkshires on Expedia.com

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Our top choices for The Berkshires hotels with a bar

1. Maya's Garden House

2. Berkshire Lake Lodge

3. Monument Mountain Motel

4. Quality Inn Lee - Lenox South

5. Holiday Inn Express Hotel & Suites Great Barrington by IHG

6. The Black Swan Lee - Lenox, an Ascend Collection Hotel

7. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

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

9. East Rock Inn

10. The Old Inn On The Green

11. The Yankee Inn

12. Hampton Inn & Suites Berkshires-Lenox

13. Berkshire Mountain Lodge

14. Quality Inn Great Barrington

15. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

16. Hotel On North

17. Hilton Garden Inn Lenox Pittsfield

18. Element by Marriott Lenox Berkshires

19. Courtyard by Marriott Lenox Berkshires

20. Chambery Inn

Top The Berkshires Hotel Reviews

Hotel On North

The Yankee Inn

Quality Inn Great Barrington

Jiminy Peak Mountain Resort

Explore a world of travel with Expedia

Find Hotels with Bars in The Berkshires, MA

Change your mind

Treat yourself

Be picky

Check availability on The Berkshires Hotels with Bars

Our top choices for The Berkshires hotels with a bar

1. Maya's Garden House

2. Berkshire Lake Lodge

3. Monument Mountain Motel

4. Quality Inn Lee - Lenox South

5. Holiday Inn Express Hotel & Suites Great Barrington by IHG

6. The Black Swan Lee - Lenox, an Ascend Collection Hotel

7. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

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

9. East Rock Inn

10. The Old Inn On The Green

11. The Yankee Inn

12. Hampton Inn & Suites Berkshires-Lenox

13. Berkshire Mountain Lodge

14. Quality Inn Great Barrington

15. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

16. Hotel On North

17. Hilton Garden Inn Lenox Pittsfield

18. Element by Marriott Lenox Berkshires

19. Courtyard by Marriott Lenox Berkshires

20. Chambery Inn

Top The Berkshires Hotel Reviews

Hotel On North

Explore a world of travel with Expedia