Hotels with Bars / Lounges, The Berkshires Massachusetts | Expedia

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Check availability on The Berkshires Hotels with Bars / Lounges

Tonight

Aug 26 - Aug 27

Tomorrow

Aug 27 - Aug 28

This weekend

Aug 28 - Aug 30

Next weekend

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 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.

A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

1. The Yankee Inn

Lenox

United States

Karen

P9,445

P10,550 total

includes taxes & fees

Sep 13 - Sep 14

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

Lenox

United States

Christine

P8,749

P9,772 total

includes taxes & fees

Sep 15 - Sep 16

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.

3. Holiday Inn Club Vacations Oak 'n Spruce Resort

South Lee

United States

Claudia

P7,220

P9,271 total

includes taxes & fees

Sep 10 - Sep 11

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 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

Stockbridge

United States

Patricia

P9,721

P13,924 total

includes taxes & fees

Sep 8 - Sep 9

A building entrance with a large planter with purple flowers and a small tree.

A restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.

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

Pittsfield

United States

Drew

P11,046

P12,338 total

includes taxes & fees

Sep 7 - Sep 8

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 large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

6. Courtyard by Marriott Lenox Berkshires

Lenox

United Kingdom

Laura

P10,967

P12,250 total

includes taxes & fees

Sep 7 - Sep 8

A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.

A hotel patio with outdoor seating and a fire pit.

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.

7. Hilton Garden Inn Lenox Pittsfield

Pittsfield

United States

James

P9,198

P10,275 total

includes taxes & fees

Sep 13 - Sep 14

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 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.

8. The Cornell Inn, Lenox & The Berkshires

Lenox

United States

Edward

P12,200

P13,993 total

includes taxes & fees

Aug 31 - Sep 1

View all properties

Top The Berkshires Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent

"This particular room, the mattress on the sifabed is worn and uncomfortable. Needs a real topper, or to be replaced. I slept on the couch, not in the bed, with a sheet on it."

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good

"We have been coming for the last few years. Generally, 4 or 5 times a year. We love the Berkshires. People vote with their feet. It is a good value. We will be back."

The Yankee Inn

The Yankee Inn

8/10 Good

"Almost two hotels in one. Several structures. One nicely updated, all check-ins, breakfast. Our stay was in an older building… while it was clean there was a musty smell. The room was very dated and the ac was loud… Time to upgrade that building."

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent

"Fine place to stay in the Lenox area."

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