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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 19 - Oct 20
Tomorrow
Oct 20 - Oct 21
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

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 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
NT$3,435
NT$3,836 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 cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.
An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".
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.

2. Berkshires Untold

Berkshires Untold
Lenox
United States
Madhavi R
NT$4,218
NT$4,712 total
includes taxes & fees
Nov 1 - Nov 2
Berkshires Untold
A building entrance with a large planter with purple flowers and a small tree.
A library with bookshelves, a television, and two armchairs.
A restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.
A spacious room with a large window, a brick wall, a sofa set, and a patterned carpet.

3. Hotel On North

Hotel On North
Pittsfield
United States
Devon
NT$4,345
NT$4,853 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 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.

4. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
United States
Vandhana
NT$4,070
NT$4,546 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 hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

5. 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
NT$3,791
NT$4,868 total
includes taxes & fees
Oct 26 - Oct 27
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
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.

6. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United Kingdom
judith
NT$4,972
NT$5,703 total
includes taxes & fees
Oct 27 - Oct 28
The Cornell Inn, Lenox & The Berkshires
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A bar with wooden floors and shelves filled with bottles.
A covered porch with wicker furniture and hanging flower baskets.

7. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Mallory
NT$5,104
NT$7,311 total
includes taxes & fees
Nov 4 - Nov 5
The Red Lion Inn
A hotel patio with outdoor seating and a fire pit.
A modern reception area with a green textured wall, a reception desk, and a coffee machine.
A modern kitchen with a marble countertop, stainless steel appliances, and a variety of food items displayed on the counter.
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

8. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
United States
James
NT$4,143
NT$4,628 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Lenox Pittsfield
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.
An outdoor seating area with Adirondack chairs and a fire feature.
A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.

9. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
United States
Francis
NT$4,374
NT$4,886 total
includes taxes & fees
Nov 8 - Nov 9
Element by Marriott Lenox Berkshires
A cozy reading nook with a bookshelf, two armchairs, a round table, and a floor lamp.
A large, multi-story building with a prominent stone facade and a metal roof, surrounded by landscaped gardens and a pedestrian bridge.
A spacious living area with a fireplace, wooden beams, and a large window.
A spacious interior with a wooden staircase, a seating area with patterned cushions, and large windows allowing natural light.

10. The Williams Inn

The Williams Inn
Williamstown
United States
Joshua
NT$6,582
NT$7,352 total
includes taxes & fees
Nov 11 - Nov 12
The Williams Inn
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Top The Berkshires Hotel Reviews

Hotel On North

Hotel On North

10/10 Excellent
"Well maintained and updated property. Very kind and helpful team."
Michele 1-night trip
Posted 3 hours ago
Hotel On North
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

8/10 Good
"Cuisine bien équipée beau site. Un peu vieillot. La porte du lave vaisselle était brisée mais il fonctionnait tout de même bien. On avait un bac avec sel et poivre et sucre en plus que des filtres et sachets à café. Un beau gros four/air fryer dans la chambre également qui était très pratique. Des couverts pour 6 personnes.Jy retournerais sans hésitation . Le lit était confortable. Les oreillers un peu moins"
Gabriel 2-night trip
Posted 9 hours ago
Jiminy Peak Mountain Resort
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Amazing experience, Great for families,nearby many trails and scenic driveway! Will be back certainly"
Chui shan 1-night trip
Posted 9 hours ago
Vacation Village in the Berkshires
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"Great place to stay, super friendly staff. All that the Lenox and Lee had to offer isn't far. Will stay again."
Jason 1-night trip
Posted 13 hours ago
The Cornell Inn, Lenox & The Berkshires
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"-"
Serena 1-night trip
Posted 1 day ago
Quality Inn Great Barrington
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Would stay here again for sure"
Jennifer 1-night trip
Posted 2 days ago
Hotel Downstreet, an Ascend Collection Hotel

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