20 Best B&B in Cheshire, MA - Bed and Breakfast from ￥17,435

A lake surrounded by autumn-colored trees and hills.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Our top choices for Cheshire bed & breakfast

1. Harbour House Inn

Cheshire

Gregory

￥38,703 total

includes taxes & fees

Oct 1 - Oct 2

2. The Trail in Adams - Berkshires’ Art Hotel

Adams

Jenna

￥29,019 total

includes taxes & fees

Sep 21 - Sep 22

3. Shaker Mill Inn

West Stockbridge

Mervin

￥25,643 total

includes taxes & fees

Sep 21 - Sep 22

4. The Cornell Inn, Lenox & The Berkshires

Lenox

Rosann

￥29,599 total

includes taxes & fees

Sep 21 - Sep 22

5. Whistler's Inn Bed & Breakfast

Lenox

Mary Anna

￥25,864 total

includes taxes & fees

Sep 21 - Sep 22

6. Cozy Farmhouse Retreat - Ram Dass Room

Rowe

￥17,435 total

includes taxes & fees

Sep 24 - Sep 25

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

￥35,844 total

includes taxes & fees

Sep 22 - Sep 23

8. Chambery Inn

Lee

Alexandra

￥45,420 total

includes taxes & fees

Oct 21 - Oct 22

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Top Cheshire Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

"Love this place for a weekend getaway."

The Red Lion Inn

8/10 Good

"Bedding and bed were lovely. excellent to have good lighting at sink as well as a magnified mirror! Often lacking in places we have stayed. AC had trouble cooling the room down until we turned it on full blast. too much ambient light from floodlight on property next door and from hall (I finally turned off hallway light which helped. ) Common areas and halls need some brightening up with fresh, lighter paint--seemed dingy. Was terribly frustrating trying to make the Nespresso machine work. We do not own one and there were NO INSTRUCTIONS. You should assume people do not know how to operate any appliances like that and should have a card with directions. We gave up and went to the Tavern where we had lovely coffee and breakfast. Also had a great dinner in Tavern after our arrival. The patch burrata salad was superb. As was our waitress."

Find out more about Cheshire

Cheshire B&B information

Number of reviews	1,502
Accommodation	46 B&B
Lowest Price	￥17,435
Highest Price	￥98,016

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.

Explore a world of travel with Expedia

More ways to book

Book B&B in Cheshire on Expedia.com

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. Shaker Mill Inn

4. The Cornell Inn, Lenox & The Berkshires

5. Whistler's Inn Bed & Breakfast

6. Cozy Farmhouse Retreat - Ram Dass Room

7. Inn at Silver Maple Farm

8. Chambery Inn

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

10. Cozy Retreat in historic Farmhouse - Tranquility Room

11. The Inn at Stockbridge

12. Experience Timeless Elegance in The Edith Wharton Room!

13. Devonfield Inn B&B

14. Brook Farm Inn

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

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

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

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

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

20. Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

Top Cheshire Hotel Reviews

Vacation Village in the Berkshires

Berkshires Untold

The Black Swan Lee - Lenox, an Ascend Collection Hotel

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

Howard Johnson by Wyndham Lenox

Hotel Downstreet, an Ascend Collection Hotel

The Red Lion Inn

Find out more about Cheshire

Cheshire B&B information

Frequently asked questions

Explore a world of travel with Expedia

Find Cheshire Bed And Breakfast

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. Shaker Mill Inn

4. The Cornell Inn, Lenox & The Berkshires

5. Whistler's Inn Bed & Breakfast

6. Cozy Farmhouse Retreat - Ram Dass Room

7. Inn at Silver Maple Farm

8. Chambery Inn

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

10. Cozy Retreat in historic Farmhouse - Tranquility Room

11. The Inn at Stockbridge

12. Experience Timeless Elegance in The Edith Wharton Room!

13. Devonfield Inn B&B

14. Brook Farm Inn

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

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

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

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

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

20. Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

Top Cheshire Hotel Reviews

Vacation Village in the Berkshires

Find out more about Cheshire

Cheshire B&B information

Frequently asked questions

Explore a world of travel with Expedia