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Hotels with Bars / Lounges in The Berkshires

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Check availability on The Berkshires Hotels with Bars / Lounges

Tonight
29 Aug - 30 Aug
Tomorrow
30 Aug - 31 Aug
Next weekend
4 Sept - 6 Sept
In two weeks
11 Sept - 13 Sept

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

1. The Yankee Inn

The Yankee Inn
Lenox
United States
Karen
S$216
includes taxes & fees
27 Sept - 28 Sept
The Yankee Inn
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A backyard with a swimming pool, lounge chairs, and a hot tub.
A bar with wooden floors and shelves filled with bottles.
A covered porch with wicker furniture and hanging flower baskets.

2. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Patricia
S$276
includes taxes & fees
29 Sept - 30 Sept
The Red Lion 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.
A cozy library with bookshelves, a fireplace, and comfortable seating.
An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".

3. Berkshires Untold

Berkshires Untold
Lenox
United States
Christine
S$199
includes taxes & fees
28 Sept - 29 Sept
Berkshires Untold
A living room with a sofa, armchair, coffee table, and a patterned rug.
A café with a display case, a frozen food section, and a marketplace sign.
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
S$191
includes taxes & fees
9 Sept - 10 Sept
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 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
S$254
includes taxes & fees
9 Sept - 10 Sept
Hotel On North
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.
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.

6. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
United Kingdom
Laura
S$252
includes taxes & fees
9 Sept - 10 Sept
Courtyard by Marriott Lenox Berkshires
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 modern living room with a fireplace, comfortable seating, and a large window with curtains.

7. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United States
Edward
S$289
includes taxes & fees
31 Aug - 1 Sept
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 spacious living room with a large sofa, a coffee table, and a fireplace.
A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.
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
S$219
includes taxes & fees
13 Sept - 14 Sept
Hilton Garden Inn Lenox Pittsfield
A large, multi-story building with a prominent stone facade and a metal roof, surrounded by landscaped gardens and a pedestrian bridge.
A spacious living area with a fireplace, wooden beams, and a large window.
A bar area with wooden beams, red chairs, and a long wooden table.
An outdoor seating area with stone fire pit, chairs, and a red building in the background.

9. The Williams Inn

The Williams Inn
Williamstown
United States
John
S$365
includes taxes & fees
15 Sept - 16 Sept
The Williams Inn
Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.
Two people sitting by a campfire in a wooded area with benches and a clear view of the surrounding trees.
A row of colorful Victorian-style houses with a prominent red one labeled "PORCHES."
A hallway with a collection of plates on the walls, leading to a staircase.

10. The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA
North Adams
United States
Floyd
S$263
includes taxes & fees
29 Sept - 30 Sept
The Porches Inn at Mass MoCA
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Top The Berkshires Hotel Reviews

Hotel On North

Hotel On North

10/10 Excellent
"One of my favorite hotels in America - for real!"
Martha 2-night trip
Posted 13 hours ago
Hotel On North
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"
Dorothy 1-night trip
Posted 16 hours ago
The Red Lion Inn
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"Room was"
Christopher 1-night trip
Posted 21 hours ago
The Cornell Inn, Lenox & The Berkshires
The Yankee Inn

The Yankee Inn

10/10 Excellent
"One of the quietest rooms we have ever stayed in. The location was very convenient to sites in both Lenox and Stockbridge."
Stacia 1-night trip
Posted 2 days ago
The Yankee Inn
The Little Lion

The Little Lion

8/10 Good
"Clean and comfortable room for reasonable price. Central area/lobby is nice place to sit and read, relax, and/or eat breakfast (coffee provided). Also red Adirondack chairs up on hill behind rooms and small tables/chairs in front of some rooms. Can use the outdoor pool and whirl pool a few miles away at the Red Lion Inn, which is desirable feature on summer days. A few negatives. While the building and rooms are set back from the road, it’s located off a busy road that goes between Stockbridge and Great Barrington. You will hear the cars during the day. It’s also not what I would consider an “Inn” as it’s really a motel. It used to be the Briarcliff Motel before the Red Lion Inn purchased it. Any questions, requests, or comments need to contact them as the Little Lion didn’t have any full time staff and no one at front desk in the lobby when we stayed. We received text with code for room door."
Bruce 1-night trip
Posted 3 days ago
The Little Lion
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Nice place"
Peter 1-night trip
Posted 3 days ago
Hotel Downstreet, an Ascend Collection Hotel
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."
Anthony 1-night trip
Posted 4 days ago
Best Western Plus Berkshire Hills Inn & Suites

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