Berkshire County Bed And Breakfast 2026

A historic building with a tall tower, surrounded by lush green trees and a well-maintained lawn.

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Top Cities in Berkshire County

A town hall with a central dome and columns, surrounded by trees and people.

A street lined with brick buildings, one with a red awning and a sign reading "Shear Madness Salon".

Our top choices for Berkshire County bed & breakfast

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

1. The Cornell Inn, Lenox & The Berkshires

Lenox

judith

￥27,611 total

includes taxes & fees

Oct 27 - Oct 28

A red building with a sign reading "Shaker Mill Inn."

2. Shaker Mill Inn

West Stockbridge

Mahadeva

￥19,618 total

includes taxes & fees

Nov 2 - Nov 3

3. Wilder House Berkshires

Sheffield

Liliana

￥28,713 total

includes taxes & fees

Nov 2 - Nov 3

A wooden cabin interior with a dining area featuring two white chairs, a table with a coffee pot and a cup, and a view into the kitchen through an open doorway.

4. The Trail in Adams - Berkshires’ Art Hotel

Adams

Susan

￥25,574 total

includes taxes & fees

Nov 1 - Nov 2

A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

5. Brook Farm Inn

Lenox

Carrie

￥35,338 total

includes taxes & fees

Oct 29 - Oct 30

A two-story building with a sign reading "Chambéry Inn".

6. Chambery Inn

Lee

Alexandra

￥39,266 total

includes taxes & fees

Nov 3 - Nov 4

A dining table with pastries, a coffee pot, and a vase of sunflowers.

7. Granville House

Housatonic

Cynthia

￥44,683 total

includes taxes & fees

Nov 1 - Nov 2

A large, two-story house with a well-maintained lawn and a fence.

8. Devonfield Inn B&B

Lee

Sebastien

￥64,657 total

includes taxes & fees

Nov 2 - Nov 3

A two-story house with a brick entrance and a white facade.

9. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Stockbridge

Philippe

￥61,604 total

includes taxes & fees

Nov 26 - Nov 27

A two-story building with a central entrance, a porch with railings, and a sign indicating 'The Berkshire Mountain Inn.'

10. The Berkshire Mountain Inn

Great Barrington

Courtney

A modern bathroom with a glass shower, white marble walls, and a large window.

11. 33 Main

Lenox

James

A wooden deck with wicker furniture and a view of a lake.

12. Lakehouse Inn

Lee

Kathleen

A well-appointed bedroom with a large bed, a bedside table, a chair, and a bathroom visible through an open door.

13. Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

Lenox

￥50,822 total

includes taxes & fees

Oct 27 - Oct 28

A garden with a white gazebo, a brick pathway, and various plants and flowers.

14. Whistler's Inn Bed & Breakfast

Lenox

Mary Anna

￥24,128 total

includes taxes & fees

Oct 27 - Oct 28

15. The Inn at Stockbridge

Stockbridge

Kimberly

￥67,113 total

includes taxes & fees

Nov 12 - Nov 13

A covered porch with wicker furniture, a table, and hanging plants.

16. Eastgate Inn B&B

Lenox

William

A well-lit room with a staircase, a table with books, a lamp, and a bonsai tree.

17. Inn at Kenmore Hall

Richmond

Margaret

A large, two-story building with a symmetrical facade, multiple windows, and a central entrance with a covered porch.

18. Harbour House Inn

Cheshire

Gregory

￥42,066 total

includes taxes & fees

Oct 28 - Oct 29

A wooden deck with a table and chairs, surrounded by a metal railing, overlooking a lush green landscape with trees.

19. The Red Door B&B

Lee

Anonymous traveler

￥43,894 total

includes taxes & fees

Oct 27 - Oct 28

A neatly made bed with a headboard, a bedside lamp, a framed painting, and a small bedside table with a tissue box.

20. Experience Timeless Elegance in The Edith Wharton Room!

Lenox

￥50,822 total

includes taxes & fees

Oct 27 - Oct 28

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Top Berkshire County Hotel Reviews

Hotel On North

10/10 Excellent

"Perfect for our weekend family trip. Staff was super friendly. Walkable to multiple bakeries/cafes for breakfast. Walls are a little thin so noise can be a problem but otherwise no complaints."

Vacation Village in the Berkshires

10/10 Excellent

"We had a great 2 night stay in a 2 bedroom deluxe suite with our 5-person family for Family Weekend at Williams College, as our daughter just started her college career there. The accommodations were perfect, immaculate, comfortable, spacious and exactly what we needed. We had fun in the pool and playing pool - and the outdoor hotter looked inviting although it was busy so we didn't get into it on this trip. Looking forward to staying again, perhaps when there's some snow on the ground! Highly recommend staying at this lovely resort!"

Berkshire Mountain Lodge

10/10 Excellent

"We loved our experience here. The rooms were better than we could have imagined. Having a full kitchen and separate bedroom on vacation is beyond brilliant. The pool was pretty awesome - sunset looks pretty great through the back windows. They show a movie in the common room on their big TV every night. If you want an old school meet the other visitors experience, you could probably have it. There is laundry on every floor. I think the awesome prices we got were due to it not being ski season? once we go there and did some driving around we realized Bousquet mountain was right there. So probably a brilliant choice for a long family ski trip. There are a couple of really convenient grocery stores and restaurants right there - but most of the tourist attractions and pittsfield downtown are 10minute or so drive away. Beautiful lobby/property. Enjoyed the coffee machine in the library. Really great experience. We'd love to stay again."