Top Hotels in Berkshire County - Compare Berkshire County Hotels

Berkshire County Accommodation: Most Popular Cities to Stay

A building with a marquee sign reading "MAHAIWE Performing Arts Center" and a smaller sign for "Black Violin" performances.

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Our top choices for Berkshire County hotels

1. Vacation Village in the Berkshires

Williamstown

Carol

includes taxes & fees

15 Nov - 16 Nov

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

2. Berkshire Mountain Lodge

Pittsfield

Susan J

includes taxes & fees

6 Dec - 7 Dec

Two Adirondack chairs facing a river with a forested hill in the background.

3. The Yankee Inn

Lenox

Stephanie

includes taxes & fees

12 Dec - 13 Dec

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.

4. Berkshires Untold

Lenox

Juan

includes taxes & fees

17 Nov - 18 Nov

A breakfast bar with bread, a coffee machine, and a fruit basket.

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

Lee

Tina

includes taxes & fees

13 Dec - 14 Dec

A wooden house with a porch, surrounded by trees and a body of water.

6. Prospect Berkshires

Egremont

Sunny

includes taxes & fees

1 Dec - 2 Dec

An aerial view of a residential area with a prominent white building with a dark roof, surrounded by autumn-colored trees.

7. The Red Lion Inn

Stockbridge

Lisabeth

includes taxes & fees

29 Nov - 30 Nov

A snow-covered outdoor area with a patio, seating, and a covered dining area.

8. The Cornell Inn, Lenox & The Berkshires

Lenox

judith

includes taxes & fees

16 Nov - 17 Nov

An indoor swimming pool with clear water, tiled floors, and a blue wall.

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

Pittsfield

Ruth

includes taxes & fees

13 Dec - 14 Dec

A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

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

South Lee

Michael

includes taxes & fees

15 Nov - 16 Nov

A large, multi-story building with a prominent stone facade and a metal roof, surrounded by landscaped gardens and a pedestrian bridge.

11. The Williams Inn

Williamstown

Pete

includes taxes & fees

15 Nov - 16 Nov

A cozy living room with a stone fireplace, comfortable seating, and a welcoming sign.

12. Jiminy Peak Mountain Resort

Hancock

Olga

includes taxes & fees

22 Nov - 23 Nov

A large house with a covered patio area featuring outdoor seating and a fire pit.

13. The Whitlock

Lenox

Beverly

includes taxes & fees

17 Nov - 18 Nov

A reception area with a large landscape painting, a dark reception desk, and a potted plant.

14. Hotel Downstreet, an Ascend Collection Hotel

North Adams

marwan

includes taxes & fees

7 Dec - 8 Dec

A wooden fire pit surrounded by six Adirondack chairs in a forested area.

15. Little Cat Lodge

Copake Falls

Nutcha

includes taxes & fees

18 Nov - 19 Nov

Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.

16. The Porches Inn at Mass MoCA

North Adams

Evonne

includes taxes & fees

15 Dec - 16 Dec

A multi-story hotel with a classic facade, large windows, and a prominent entrance.

17. Hotel On North

Pittsfield

Rosemarie

includes taxes & fees

29 Nov - 30 Nov

An outdoor patio area with a circular fire pit surrounded by wicker furniture and a stone fire table.

18. Courtyard by Marriott Lenox Berkshires

Lenox

Vandhana

includes taxes & fees

13 Dec - 14 Dec

A spacious hotel lobby with multiple seating areas, large windows, and a television.

19. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

includes taxes & fees

15 Dec - 16 Dec

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

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

Great Barrington

includes taxes & fees

18 Nov - 19 Nov

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Great weekend hotel deals in Berkshire County, MA

Showing deals for:27 Nov - 29 Nov

Berkshire Mountain Lodge

Pittsfield

9.0/10Wonderful (1,272 reviews)

Member Price available

for 2 nights, 1 room

£109 per night

includes taxes & fees

Hotels recommended for families in Berkshire County

The Yankee Inn

Lenox

includes taxes & fees

12 Dec - 13 Dec

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Top Berkshire County Hotel Reviews

Vacation Village in the Berkshires

8/10 Good

"The staff were super kind and helpful, however there were some concerns. The indoor pool was closed because there were too many pool chemicals in it, which was tough since that was a primary reason for choosing this property. This meant that the families with children were relegated to the hot tub and pool table areas because the arcade area costs money to play. The staff were kind, but the lack of swimming pool and the abundance of bored children arouns changed the atmosphere. "Too many chemicals" in the pool seems like an avoidable problem. The room was lovely, but we had to take out our own trash and wash our own dishes which wasn't quite "vacation vibes" since this was listed as a hotel. Loved the gas fireplace, but it does run on by using a dial on the wall that makes a ticking sound constantly. The walls were super thin, so I could see where that would be a challenge during busy season. Honestly, I feel like the whole property would feel kind of feral during busy season with so many "first come, first served" elements, but the mountain views were gorgeous and the staff were very very kind and helpful. Also, the room was beautifully clean and cozy, which is always a nice feeling."