A person snowboarding down a snowy slope.

Search Hotels with a Bar in The Berkshires

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on The Berkshires Hotels with a Bar

Tonight
27 Sept - 28 Sept
Tomorrow
28 Sept - 29 Sept
Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct

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 view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

1. The Yankee Inn

The Yankee Inn
Lenox
United States
William
£91
includes taxes & fees
27 Oct - 28 Oct
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 cozy library with bookshelves, a fireplace, and comfortable seating.

2. Berkshires Untold

Berkshires Untold
Lenox
United States
Drue
£125
includes taxes & fees
29 Sept - 30 Sept
Berkshires Untold
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 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
Jared
£113
includes taxes & fees
30 Sept - 1 Oct
Holiday Inn Club Vacations Oak 'n Spruce Resort
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 modern restaurant with wooden flooring, bar area, and seating arrangements.
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.

4. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
United States
Tracy
£119
includes taxes & fees
25 Oct - 26 Oct
Courtyard by Marriott Lenox Berkshires
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 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
£113
includes taxes & fees
5 Oct - 6 Oct
Hotel On North
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A bar with wooden floors and shelves filled with bottles.
A covered porch with wicker furniture and hanging flower baskets.

6. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Stephan
£169
includes taxes & fees
29 Sept - 30 Sept
The Red Lion 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.

7. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United States
Rosann
£133
includes taxes & fees
27 Oct - 28 Oct
The Cornell Inn, Lenox & The Berkshires
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.
A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.
A spacious living room with a large sofa, a coffee table, and a fireplace.
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
£123
includes taxes & fees
4 Oct - 5 Oct
Hilton Garden Inn Lenox Pittsfield
An indoor swimming pool with clear pool rules signage, multiple seating areas, and a view of the outdoors through large windows.
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.

9. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
United States
Debra
£94
includes taxes & fees
29 Oct - 30 Oct
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A large, multi-story building with a prominent stone facade and a metal roof, surrounded by landscaped gardens and a pedestrian bridge.
A spacious interior with a wooden staircase, a seating area with patterned cushions, and large windows allowing natural light.
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
William
£156
includes taxes & fees
29 Sept - 30 Sept
The Williams Inn
View all properties

Top The Berkshires Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Another great stay at VV. My hallway got flooded by a broken hot water heater on my first morning there (Friday), they got a property restoration co in to start cleanup right away but between the industrial fans blowing round the clock and stagnant odor from the soaked carpet hanging heavy all the way up and down the hall, if I hadn’t been checking out today (Sunday) I would have requested to move units for the rest of my stay. Staff was super professional, apologetic, this was not their fault, and I will happily book again at VV in the future."
Elizabeth 3-night trip
Posted 3 hours ago
Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

10/10 Excellent
"There was a nice set up for the complimentary breakfast."
Allison 2-night trip
Posted 9 hours ago
The Yankee Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Front desk guy was great very helpful.. rooms were clean,good location"
Michael 1-night trip
Posted 9 hours ago
Quality Inn Great Barrington
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Another unforgettable experience at the Red Lion. My family has been coming up for 50 years, we’re happy to continue the tradition. Wether Fall, Spring, Summer or Winter, the 4 seasons at the Red Lion are always a favorite!"
Nelson 1-night trip
Posted 12 hours ago
The Red Lion 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 4 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 6 days ago
Jiminy Peak Mountain Resort

Explore a world of travel with Expedia