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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
Sep 1 - Sep 2
Tomorrow
Sep 2 - Sep 3
This weekend
Sep 4 - Sep 6
Next weekend
Sep 11 - Sep 13

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 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
Karen
NT$2,738
NT$3,059 total
includes taxes & fees
Sep 28 - Sep 29
The Yankee Inn
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.
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.
A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.

2. Berkshires Untold

Berkshires Untold
Lenox
United States
Christine
NT$4,433
NT$4,951 total
includes taxes & fees
Sep 28 - Sep 29
Berkshires Untold
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A bar with wooden floors and shelves filled with bottles.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A backyard with a swimming pool, lounge chairs, and a hot tub.

3. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Patricia
NT$5,231
NT$7,414 total
includes taxes & fees
Sep 3 - Sep 4
The Red Lion Inn
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 multi-story building with a symmetrical facade, multiple balconies, and a central tower.
An indoor swimming pool with clear water, a lifeguard station, and a sign indicating no lifeguard on duty.

4. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
United States
Claudia
NT$3,472
NT$4,496 total
includes taxes & fees
Sep 16 - Sep 17
Holiday Inn Club Vacations Oak 'n Spruce Resort
A building entrance with a large planter with purple flowers and a small tree.
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.
A lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.

5. Hotel On North

Hotel On North
Pittsfield
United States
Drew
NT$4,253
NT$4,750 total
includes taxes & fees
Sep 9 - Sep 10
Hotel On North
A snow-covered outdoor area with a patio, seating, and a covered dining area.
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.
A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.

6. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United States
FRED
NT$6,423
NT$7,367 total
includes taxes & fees
Sep 10 - Sep 11
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 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.
A modern restaurant with wooden flooring, bar area, and seating arrangements.

7. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
United Kingdom
Laura
NT$5,627
NT$6,286 total
includes taxes & fees
Sep 7 - Sep 8
Courtyard by Marriott Lenox Berkshires
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.
A spacious living room with a large sofa, a coffee table, and a fireplace.
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.
A hotel patio with outdoor seating and a fire pit.

8. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
United States
James
NT$4,683
NT$5,231 total
includes taxes & fees
Sep 13 - Sep 14
Hilton Garden Inn Lenox Pittsfield
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.
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.
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
Lawrence
NT$5,628
NT$6,287 total
includes taxes & fees
Sep 9 - Sep 10
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 bar area with wooden beams, red chairs, and a long wooden table.
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
John
NT$7,816
NT$8,731 total
includes taxes & fees
Sep 23 - Sep 24
The Williams Inn
View all properties

Top The Berkshires Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"It is a good value for money. Location is very good, right on the main street, just one block away from downtown Great Barrington with almost all the restaurants and shops within walking distance. Downside is that it is a motel, not a standard hotel. If you have a room on the second floor then you have to haul your luggage up as there is no elevator. Breakfast has bare minimum items. It would help if fresh fruit and cereal is added. There is improvement possible in the overall upkeep. However, I'll certainly recommend it for a short stay for budget customers like me."
SANJAY 2-night trip
Posted 3 hours ago
Quality Inn Great Barrington
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"Lovely people and place. Breakfast was great and so was the room. Highly recommend."
FRED 1-night trip
Posted 1 day ago
The Cornell Inn, Lenox & The Berkshires
Hotel On North

Hotel On North

8/10 Good
"Nice room! Comfortable bed. Super friendly staff."
Jana 1-night trip
Posted 2 days ago
Hotel On North
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

8/10 Good
"It was clean and amenities were above average."
Prasanna 1-night trip
Posted 2 days ago
Best Western Plus Berkshire Hills Inn & Suites
Willows Motel Williamstown

Willows Motel Williamstown

10/10 Excellent
"Our one-night stay at Willows Motel was very pleasant. The staff/managers/owners were friendly and helpful, our room was comfortable and clean. We were easily able to control the temperature with up-to-date air conditioning. The free continental breakfast was healthy and generous, including a plentiful assortment of fruits, nuts, dates, etc. to accompany the cereal, breads, bagels, etc. We also appreciated the well-kept small garden areas around the property. We would choose the Willows Motel again if we are staying in the Williamstown area."
Carol 1-night trip
Posted 2 days ago
Willows Motel Williamstown
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Nice to have a kitchenette to cook in"
Jacqueline 1-night trip
Posted 2 days ago
Jiminy Peak Mountain Resort
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"We were there for one night and it worked out great. Nice breakfast!"
Erlinde 1-night trip
Posted 8 days ago
Hampton Inn & Suites Berkshires-Lenox

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