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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 29 - Sep 30
Tomorrow
Sep 30 - Oct 1
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

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 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
William
NT$3,430
NT$3,831 total
includes taxes & fees
Oct 27 - Oct 28
The Yankee Inn
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 covered outdoor area with stone pillars and a view of a road and green hills.

2. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
United States
Tracy
NT$4,494
NT$5,020 total
includes taxes & fees
Oct 25 - Oct 26
Courtyard by Marriott Lenox Berkshires
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.
A cozy library with bookshelves, a fireplace, and comfortable seating.
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.

3. Berkshires Untold

Berkshires Untold
Lenox
United States
Drue
NT$4,969
NT$5,551 total
includes taxes & fees
Sep 30 - Oct 1
Berkshires Untold
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 two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.
A dining area with a glass table, red walls, and framed artwork.

4. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United States
Rosann
NT$4,873
NT$5,589 total
includes taxes & fees
Oct 27 - Oct 28
The Cornell Inn, Lenox & The Berkshires
A building with a porch and multiple windows, surrounded by purple flowers.
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.

5. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
United States
Jared
NT$3,715
NT$4,771 total
includes taxes & fees
Oct 19 - Oct 20
Holiday Inn Club Vacations Oak 'n Spruce Resort
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A covered porch with wicker furniture and hanging flower baskets.
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.

6. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Stephan
NT$5,645
NT$7,883 total
includes taxes & fees
Oct 19 - Oct 20
The Red Lion Inn
A building entrance with a large planter with purple flowers and a small tree.
A spacious room with a large window, a brick wall, a sofa set, and a patterned carpet.
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.

7. Hotel On North

Hotel On North
Pittsfield
United States
Drew
NT$4,266
NT$4,766 total
includes taxes & fees
Oct 5 - Oct 6
Hotel On North
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.
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.
A spacious living room with a large sofa, a coffee table, and a fireplace.

8. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
United States
James
NT$4,649
NT$5,193 total
includes taxes & fees
Oct 25 - Oct 26
Hilton Garden Inn Lenox Pittsfield
Room
A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.
A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.
A conference room with a whiteboard, tables, and chairs.

9. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
United States
Debra
NT$3,273
NT$3,656 total
includes taxes & fees
Oct 29 - Oct 30
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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.

10. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
United States
Kirsty
NT$5,371
NT$5,999 total
includes taxes & fees
Oct 18 - Oct 19
Element by Marriott Lenox Berkshires
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Top The Berkshires Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"I typically do not reserve in motel with parking in front of each space due to security, I was mistaken at this facility. Pleasant neighborhood and the building was situated well off the main street."
Peter 1-night trip
Posted 21 hours ago
Quality Inn Great Barrington
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"One of the most unique establishments in the US. It brings one back to time when life was much simpler. Highly recomended."
Michael 1-night trip
Posted 1 day ago
The Red Lion Inn
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Nice room. Exceptionally clean. Great staff"
Daniel 3-night trip
Posted 1 day ago
The Yankee Inn
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Great location; walkable to restaurants. Spacious 7th floor room had a nice town and mountain view. All staff friendly and helpful. Bed was comfortable; room very clean. Breakfast was minimal and uninspiring."
Karl 1-night trip
Posted 6 days ago
Hotel Downstreet, an Ascend Collection Hotel
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Even in the off season it was beautiful."
Karen 1-night trip
Posted 8 days ago
Jiminy Peak Mountain Resort

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