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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
Aug 21 - Aug 22
Tomorrow
Aug 22 - Aug 23
This weekend
Aug 21 - Aug 23
Next weekend
Aug 28 - Aug 30

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 swimming pool with a surrounding deck, a stone wall, and a building in the background.
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.

1. The Yankee Inn

The Yankee Inn
Lenox
United States
Karen
NT$5,046
NT$5,637 total
includes taxes & fees
Sep 21 - Sep 22
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
Pamela
NT$4,084
NT$4,561 total
includes taxes & fees
Sep 9 - Sep 10
Berkshires Untold
A serene riverside view with a stone bridge, reflecting trees and buildings.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
A café with a display case, a frozen food section, and a marketplace sign.
A living room with a sofa, armchair, coffee table, and a patterned rug.

3. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
United States
Claudia
NT$3,737
NT$4,798 total
includes taxes & fees
Sep 21 - Sep 22
Holiday Inn Club Vacations Oak 'n Spruce Resort
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.

4. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Patricia
NT$5,315
NT$7,524 total
includes taxes & fees
Sep 14 - Sep 15
The Red Lion Inn
A building entrance with a large planter with purple flowers and a small tree.
A lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.
A spacious room with a large window, a brick wall, a sofa set, and a patterned carpet.
A restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.

5. Hotel On North

Hotel On North
Pittsfield
United States
Drew
NT$5,717
NT$6,386 total
includes taxes & fees
Sep 7 - Sep 8
Hotel On North
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 bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.

6. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
United States
James
NT$4,672
NT$5,218 total
includes taxes & fees
Sep 13 - Sep 14
Hilton Garden Inn Lenox Pittsfield
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.
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$5,674
NT$6,338 total
includes taxes & fees
Sep 7 - Sep 8
Courtyard by Marriott Lenox Berkshires
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 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.

8. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United States
Edward
NT$6,311
NT$7,239 total
includes taxes & fees
Aug 26 - Aug 27
The Cornell Inn, Lenox & The Berkshires
A modern bar area with a central island, multiple bar stools, and a seating area with tables and chairs.
A banquet hall with round tables set for a formal event, featuring white tablecloths, silverware, and floral centerpieces.
A Holiday Inn & Suites hotel with a modern design, featuring a prominent sign and a well-lit entrance.
A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.

9. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
United States
Myrna
NT$3,801
NT$4,245 total
includes taxes & fees
Sep 20 - Sep 21
Holiday Inn & Suites Pittsfield-Berkshires by IHG
An outdoor seating area with Adirondack chairs and potted plants.
A hotel room with a large bed, two bedside lamps, a nightstand, a framed picture on the wall, and a window with curtains.
A building with a double door labeled "WELCOME" and "OFFICE," a "PARKING ONLY" sign, and flower baskets on either side of the entrance.
A reception area with a bulletin board, a 'no smoking' sign, a clock, and a 'STOP' sign.

10. Cozy Corner Motel

Cozy Corner Motel
Williamstown
United States
Jeremy
NT$2,817
NT$3,311 total
includes taxes & fees
Sep 20 - Sep 21
Cozy Corner Motel
View all properties

Top The Berkshires Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good
"."
Mark 3-night trip
Posted 8 hours ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"We come up to the Berkshires every year for Tanglewood and always stay here. The rooms are always clean and the staff friendly and helpful. The rooms have either a full kitchen or kitchenette so at the very least you can have coffee when you wake-up. The fact that Vacation Village is on Brodie Mountain it's quiet and restful."
William 3-night trip
Posted 16 hours ago
Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

10/10 Excellent
"What a wonderful stay! It was an impromptu overnight to the Berkshires and I’m so glad we chose to stay here. Our room was beautiful and clean, with a lovely view of the pond area out back from the balcony. Great bathroom and shower, very clean. Breakfast was yummy with a nice selection. The pools and hot tub were the BEST part. I absolutely will be back because one night was certainly not enough."
Kelly 1-night trip
Posted 1 day ago
The Yankee Inn
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"…."
Tiago 3-night trip
Posted 3 days ago
Jiminy Peak Mountain Resort
Hotel On North

Hotel On North

10/10 Excellent
"A great location for a concert at Tanglewood and a chance to explore a new city. Parking is easy and convenient. The staff is very welcoming and helpful. The facilities are clean, modern, quiet, and vintage at the same time. A beautiful bar and restaurant on site and many restaurants and coffee shops in walking distance. I would definitely stay here again!"
Amy 1-night trip
Posted 4 days ago
Hotel On North

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