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Hotels with Entertainment in The Berkshires

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Check availability on The Berkshires Hotels with Entertainment

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov

Our top choices for The Berkshires hotels with entertainment

A grassy area with a lake, trees, and red chairs arranged around a fire pit.

1. Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
9.8 out of 10, Exceptional, (27 reviews)
"excellent lakeside view"
United States
mike
The price is S$156
includes taxes & fees
8 Nov - 9 Nov
Berkshire Lake Lodge
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

2. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (821 reviews)
"Nice view and location for fall color."
United States
Md
The price is S$230
includes taxes & fees
12 Nov - 13 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

3. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (942 reviews)
"Easy access to everywhere we went. Clean"
United States
Phillip
The price is S$86
includes taxes & fees
8 Nov - 9 Nov
Monument Mountain Motel
A Holiday Inn Express & Suites building with a clear entrance, a covered parking area, and a stone facade.

4. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (854 reviews)
"Always a pleasurable stay. The rooms are clean, the amenities are appreciated, and the staff very attentive. Great location and as a single traveler I always feel safe staying here."
United States
Cynthia
The price is S$119
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A lodge with a large building and a dock by a lake, surrounded by forest.

5. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,001 reviews)
"Amazing place, clean, staff is awesome , amazing location , amazing views! Free breakfast, free coffee bar , free gym and the best it’s pet friendly !"
United States
Gustavo
The price is S$153
includes taxes & fees
3 Dec - 4 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

6. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Downtown Great Barrington
8.6 out of 10, Excellent, (1,003 reviews)
"Our room was spotless and the staff was helpful and welcoming!"
United States
Lynne
The price is S$108
includes taxes & fees
7 Dec - 8 Dec
Quality Inn Great Barrington
A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

7. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
3.5 star property
South Lee
9.2 out of 10, Wonderful, (1,002 reviews)
"Nice place to stay"
United States
Michael
The price is S$183
includes taxes & fees
8 Nov - 9 Nov
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

8. East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (58 reviews)
"East Rock was a nice, clean, and comfortable place to stay. Everything was great, and I enjoyed my stay."
United States
Sharon
The price is S$170
includes taxes & fees
8 Dec - 9 Dec
East Rock Inn
A white two-story house with a front door, windows, and a chimney.

9. The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (96 reviews)
"Lovely property.unique historic buildings and rooms with updated amenities! Quiet and peaceful beautiful dinner!"
United States
mary ellen
The price is S$449
includes taxes & fees
8 Nov - 9 Nov
The Old Inn On The Green
Two Adirondack chairs facing a river with a forested hill in the background.

10. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
"The location was good for our trip."
United States
Basil
The price is S$156
includes taxes & fees
20 Nov - 21 Nov
The Yankee Inn
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

11. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (51 reviews)
"Clean, spacious room Accommodating staff especially Shawn and Jennifer at the front desk. Very nice pool and gym Definitely coming back"
United States
Francis
The price is S$193
includes taxes & fees
15 Nov - 16 Nov
Element by Marriott Lenox Berkshires
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

12. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (688 reviews)
"Great stay!"
United States
Vandhana
The price is S$180
includes taxes & fees
15 Nov - 16 Nov
Courtyard by Marriott Lenox Berkshires
Exterior

13. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,258 reviews)
"Comfortable stay, well stocked kitchen and room."
United States
Charline
The price is S$139
includes taxes & fees
6 Dec - 7 Dec
Berkshire Mountain Lodge
An indoor swimming pool with clear water, tiled floors, and a blue wall.

14. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (257 reviews)
"The room was clean and well kept, breakfast was amazing!"
United States
Ruth
The price is S$148
includes taxes & fees
6 Dec - 7 Dec
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A multi-story hotel with a classic facade, large windows, and a prominent entrance.

15. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (981 reviews)
"Very nice hotel"
United States
Philip
The price is S$166
includes taxes & fees
29 Nov - 30 Nov
Hotel On North
A reception area with a fireplace, seating, and a doormat with the logo "Quality".

16. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.6 out of 10, Excellent, (1,002 reviews)
"Just perfect lodging place for short time travelers"
United States
Bernardo Jr
The price is S$122
includes taxes & fees
2 Dec - 3 Dec
Quality Inn Lee - Lenox South
A spacious hotel lobby with multiple seating areas, large windows, and a television.

17. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.0 out of 10, Wonderful, (1,001 reviews)
"Breakfast was great"
United States
Thomas
The price is S$157
includes taxes & fees
15 Nov - 16 Nov
Hampton Inn & Suites Berkshires-Lenox
A hotel patio with outdoor seating and a fire pit.

18. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (716 reviews)
"Great place to stay. Great staff and convenient location. Nice restaurant as well."
United States
James
The price is S$170
includes taxes & fees
15 Nov - 16 Nov
Hilton Garden Inn Lenox Pittsfield
A crowded outdoor event with tents and people gathered in a grassy area.

19. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (390 reviews)
"An absolutely perfect getaway spot! Beautiful rooms, great service, and an ideal location. Highly recommend and we will be going back."
United States
Alexandra
The price is S$259
includes taxes & fees
16 Nov - 17 Nov
Chambery Inn
A snow-covered outdoor area with a patio, seating, and a covered dining area.

20. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.4 out of 10, Exceptional, (1,002 reviews)
"Lovely room, comfortable bed and a nice breakfast."
United Kingdom
judith
The price is S$250
includes taxes & fees
9 Nov - 10 Nov
The Cornell Inn, Lenox & The Berkshires
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top The Berkshires Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Gorgeous setting, comfortable beds and luxurious accommodations."
Carol 1-night trip
Posted 8 hours ago
Vacation Village in the Berkshires
The Red Lion Inn

The Red Lion Inn

8/10 Good
"We stayed in an adjacent house owned by the hotel. When we booked we assumed we’d be in the main hotel. The “out” building was unmarked and hard to find. It was dark when we arrived and there were no porch lights. We thought the overall experience was good. Quaint but this building could benefit from some upgrades."
Randall 1-night trip
Posted 10 hours ago
The Red Lion Inn

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