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The Berkshires Hotel Guide - Hotels with Bar in The Berkshires, Massachusetts

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Check availability on The Berkshires Hotels with Bar

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

Our top choices for The Berkshires hotels with a bar

Two Adirondack chairs facing a river with a forested hill in the background.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
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.

1. The Yankee Inn

The Yankee Inn
Lenox
United States
Basil
€106
includes taxes & fees
1 Nov - 2 Nov
The Yankee Inn
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 dining area with a glass table, red walls, and framed artwork.

2. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United Kingdom
judith
€157
includes taxes & fees
27 Oct - 28 Oct
The Cornell Inn, Lenox & The Berkshires
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
€130
includes taxes & fees
1 Nov - 2 Nov
Berkshires Untold
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 restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.
A library with bookshelves, a television, and two armchairs.

4. Hotel On North

Hotel On North
Pittsfield
United States
Devon
€125
includes taxes & fees
8 Nov - 9 Nov
Hotel On North
A multi-story building with a balcony, a pond with rocks, and a tree.
A café with a display case, a frozen food section, and a marketplace sign.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.
A living room with a sofa, armchair, coffee table, and a patterned rug.

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
€134
includes taxes & fees
29 Oct - 30 Oct
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
A covered outdoor area with stone pillars and a view of a road and green hills.
A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.

6. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
United States
Vandhana
€125
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Lenox Berkshires
A hotel patio with outdoor seating and a fire pit.
A bar area with a long counter, red bar stools, and shelves with bottles and decorative items.
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.

7. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
United States
James
€118
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 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
€201
includes taxes & fees
4 Nov - 5 Nov
The Red Lion Inn
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.
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.
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
€135
includes taxes & fees
8 Nov - 9 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.
A bar area with wooden beams, red chairs, and a long wooden table.
A spacious living area with a fireplace, wooden beams, and a large window.
An outdoor seating area with stone fire pit, chairs, and a red building in the background.

10. The Williams Inn

The Williams Inn
Williamstown
United States
Pete
€203
includes taxes & fees
8 Nov - 9 Nov
The Williams Inn
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Top The Berkshires Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Great"
Sharath 1-night trip
Posted 13 hours ago
Hotel Downstreet, an Ascend Collection Hotel
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Nice Property clean rooms walked the new footpath out back always enjoy the saltwater pool."
Dan 2-night trip
Posted 13 hours ago
The Yankee Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"The hotel was clean and pleasant. Staff members were courteous and helpful! Very satisfied with our stay and will consider a future stay here!"
Anne Marie 2-night trip
Posted 16 hours ago
Quality Inn Great Barrington
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"The parking lot was being resurfaced and we could not find a handicap spot near the door. It was inconvenient, and one handicap spot was filled by a car without a handicap placard."
Marcia 1-night trip
Posted 1 day ago
Hampton Inn & Suites Berkshires-Lenox
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"Wonderful staff , great location ! Fresh brownies offered at check in , specialty cocktails in the evening , lovely breakfast in the morning:)"
Sandra 1-night trip
Posted 1 day ago
The Cornell Inn, Lenox & The Berkshires

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