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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 25 - Oct 26
Tomorrow
Oct 26 - Oct 27
Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8

Our top choices for The Berkshires hotels with a bar

Two Adirondack chairs facing a river with a forested hill in the background.
A restaurant interior with white tables, cushioned booths, and a bar area.
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.

1. The Yankee Inn

The Yankee Inn
Lenox
United States
Basil
₩140,248
₩156,654 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
A multi-story hotel with a classic facade, large windows, and a prominent entrance.
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.

2. Hotel On North

Hotel On North
Pittsfield
United States
John
₩165,519
₩184,885 total
includes taxes & fees
Nov 8 - Nov 9
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
Lenox
United States
Madhavi R
₩172,253
₩192,407 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 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.
A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.

4. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United Kingdom
judith
₩203,036
₩232,882 total
includes taxes & fees
Oct 27 - Oct 28
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.
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
Vandhana
₩166,193
₩185,637 total
includes taxes & fees
Nov 1 - Nov 2
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 balcony, a pond with rocks, and a tree.
A multi-story building with a symmetrical facade, multiple balconies, and a central tower.
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
Michael
₩154,802
₩198,780 total
includes taxes & fees
Oct 28 - Oct 29
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A hotel patio with outdoor seating and a fire pit.
A spacious living room with a large sofa, a coffee table, and a fireplace.
A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.
A bar area with a long counter, red bar stools, and shelves with bottles and decorative items.

7. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
United States
James
₩157,024
₩175,388 total
includes taxes & fees
Nov 15 - Nov 16
Hilton Garden Inn Lenox Pittsfield
A straw hat, sunglasses, and two drinks on a striped towel by a body of water.
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.
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

8. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Mallory
₩208,413
₩298,528 total
includes taxes & fees
Nov 4 - Nov 5
The Red Lion Inn
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.
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.

9. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
United States
Francis
₩178,617
₩199,515 total
includes taxes & fees
Nov 8 - Nov 9
Element by Marriott Lenox Berkshires
A wooden boat on calm water with a house in the background.
A wooden wall with a white pendant light fixture.
Room
A wooden deck with a dog silhouette against a backdrop of autumn foliage.

10. Prospect Berkshires

Prospect Berkshires
Egremont
United States
Conor
₩375,096
₩463,318 total
includes taxes & fees
Nov 9 - Nov 10
Prospect Berkshires
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Top The Berkshires Hotel Reviews

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