20 Best B&B in Cheshire, MA - Bed and Breakfast from AED 408

A lake surrounded by autumn-colored trees and hills.

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Our top choices for Cheshire bed & breakfast

1. Harbour House Inn

Cheshire

Gregory

AED 985 total

includes taxes & fees

26 Oct - 27 Oct

2. The Trail in Adams - Berkshires’ Art Hotel

Adams

Susan

AED 744 total

includes taxes & fees

28 Sep - 29 Sep

3. The Cornell Inn, Lenox & The Berkshires

Lenox

Rosann

AED 647 total

includes taxes & fees

27 Oct - 28 Oct

4. Shaker Mill Inn

West Stockbridge

Mervin

AED 721 total

includes taxes & fees

1 Oct - 2 Oct

5. Cozy Retreat in historic Farmhouse - Tranquility Room

Rowe

AED 555 total

includes taxes & fees

27 Sep - 28 Sep

6. Whistler's Inn Bed & Breakfast

Lenox

Mary Anna

AED 650 total

includes taxes & fees

5 Oct - 6 Oct

7. Inn at Silver Maple Farm

East Chatham

"We had a very pleasant stay at this. Eautiful country property. Check in was smooth and instructions were easy to follow. Our room, in the main building was well appointed. The bed was super comfortable and the amenities were fine. Breakfast was great! Common areas were lovely and inviting, and the s’mores kits in the lobby were just the thing for an evening around the outdoor fire pit. Highly recommend for anyone seeking a serene country setting."

Jody

AED 880 total

includes taxes & fees

28 Sep - 29 Sep

8. Chambery Inn

Lee

Alexandra

AED 1,108 total

includes taxes & fees

27 Sep - 28 Sep

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Top Cheshire Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"It’s an older facility , as expected, but with great character and very clean . Special praise goes to the staff , in particular , Michele at the front desk . Super nice and very helpful in answering our questions about the local activities . Will keep in mind for another visit ."

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good

"I stayed in a townhouse, an upgrade from the room I booked. It was quiet and private, which I enjoyed, and more room than I needed. If my family's schedule had been different, I could have invited them over for a cookout (they live nearby). The townhouse was rather dated and I am afraid a bit dreary, with a lot of browns and beiges. But well-outfitted and convenient."

Berkshire Mountain Lodge

8/10 Good

"One of the most important aspects of a good hotel is the smell of it when I first walk in the door. This lodge smelled clean and was clean. The second important thing is the customer service. This place was just okay. Polite but not very friendly. The third important aspect is the plumbing and that was just okay too. Workable enough so we didn’t have to ask for another room but the little soaps were tiny and the toilet was in okay condition. A little hard to flush sometimes. They act like it’s someplace special but it really isn’t. It was a good stay but nothing special. Location was convenient to everything - restaurants and stores."

Frequently asked questions

Searching for B&Bs in Cheshire?

If you want to find a place to stay with a small number of rooms and a more personalized environment, a B&B might be a great fit for your vacation to Cheshire. When you want to explore some attractions in town, Mount Greylock State Reservation and Cheshire Reservoir are worth a stop.

Why would you choose a B&B versus a traditional hotel?

B&Bs all have a unique charm. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a fun place to get away.

What are the best B&Bs in Cheshire?

Below are some well-liked B&Bs in the area: Harbour House Inn: 6 rooms. 1.2 mi (2 km) from the heart of Cheshire. Enjoy the free full breakfast and unique décor. The Cornell Inn, Lenox & The Berkshires: 14.8 mi (23.9 km) from the downtown core. Enjoy the free full breakfast and unique décor. Inn at Silver Maple Farm: 11 rooms. Situated 18.2 mi (29.3 km) from the heart of Cheshire. Enjoy the free buffet breakfast and designer toiletries. The Trail in Adams - Berkshires' Art Hotel: 9 rooms. Located 4.7 mi (7.5 km) from the core of Cheshire. Enjoy the unique décor and patio area.

What's the best time of year to book my B&B in Cheshire?

When you're planning your stay in Cheshire, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Cheshire are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

What is there to do in Cheshire?

When you want to spend some time in the great outdoors, Mount Greylock State Reservation and Cheshire Reservoir are some notable spots. You might also consider a trip to sites like Mount Greylock State Reservation Visitor Center or Mount Greylock if you have time to see more of the area.

How can I get to and around Cheshire?

Mapping out your trip in and around Cheshire is easy with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 11.5 mi (18.5 km) away from the heart of the city. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 33.6 mi (54 km) away. If you'd like to explore around the area, you may want a rental car for your journey.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cheshire bed & breakfast

1. Harbour House Inn

2. The Trail in Adams - Berkshires’ Art Hotel

3. The Cornell Inn, Lenox & The Berkshires

4. Shaker Mill Inn

5. Cozy Retreat in historic Farmhouse - Tranquility Room

6. Whistler's Inn Bed & Breakfast

7. Inn at Silver Maple Farm

8. Chambery Inn

9. Cozy Farmhouse Retreat - Ram Dass Room

10. Cozy Retreat in Historic Farmhouse, Charming Bunk Bed Room,- Owl Dorm

11. Experience Timeless Elegance in The Edith Wharton Room!

12. Devonfield Inn B&B

13. Brook Farm Inn

14. The Inn at Stockbridge

15. Cozy Carriage House room with a double bed and private balcony

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

17. Historic Susan B. Anthony Room - Cozy & Charming Stay

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

19. Elegant Carriage House room with a queen bed and private patio.

20. Elegant suite with a king bed, fireplace, and kitchenette.

Top Cheshire Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Berkshires Untold

Holiday Inn Club Vacations Oak 'n Spruce Resort

Quality Inn Lee - Lenox South

The Red Lion Inn

The Whitlock

Hampton Inn & Suites Berkshires-Lenox

Berkshire Mountain Lodge

Hotel Downstreet, an Ascend Collection Hotel

Frequently asked questions

Search B&B in Cheshire

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cheshire bed & breakfast

1. Harbour House Inn

2. The Trail in Adams - Berkshires’ Art Hotel

3. The Cornell Inn, Lenox & The Berkshires

4. Shaker Mill Inn

5. Cozy Retreat in historic Farmhouse - Tranquility Room

6. Whistler's Inn Bed & Breakfast

7. Inn at Silver Maple Farm

8. Chambery Inn

9. Cozy Farmhouse Retreat - Ram Dass Room

10. Cozy Retreat in Historic Farmhouse, Charming Bunk Bed Room,- Owl Dorm

11. Experience Timeless Elegance in The Edith Wharton Room!

12. Devonfield Inn B&B

13. Brook Farm Inn

14. The Inn at Stockbridge

15. Cozy Carriage House room with a double bed and private balcony

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

17. Historic Susan B. Anthony Room - Cozy & Charming Stay

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

19. Elegant Carriage House room with a queen bed and private patio.

20. Elegant suite with a king bed, fireplace, and kitchenette.

Top Cheshire Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Frequently asked questions