Cheshire B&B: Best Cheshire Bed and Breakfast

A lake surrounded by autumn-colored trees and hills.

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Our top choices for Cheshire bed & breakfast

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

1. Harbour House Inn

Cheshire

Gregory

includes taxes & fees

29 Oct - 30 Oct

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.

2. The Trail in Adams - Berkshires’ Art Hotel

Adams

Susan

includes taxes & fees

26 Oct - 27 Oct

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

3. The Cornell Inn, Lenox & The Berkshires

Lenox

judith

includes taxes & fees

27 Oct - 28 Oct

A house with a chimney, surrounded by trees with autumn foliage.

4. UU Rowe Camp and Conference Center

Rowe

Stuart

includes taxes & fees

28 Oct - 29 Oct

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

5. Shaker Mill Inn

West Stockbridge

Mahadeva

includes taxes & fees

2 Nov - 3 Nov

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

6. Whistler's Inn Bed & Breakfast

Lenox

Mary Anna

includes taxes & fees

24 Oct - 25 Oct

7. Cozy Farmhouse Retreat - Ram Dass Room

Rowe

includes taxes & fees

27 Oct - 28 Oct

An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

8. Inn at Silver Maple Farm

East Chatham

Linda

includes taxes & fees

22 Nov - 23 Nov

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Top Cheshire Hotel Reviews

Quality Inn Lee - Lenox South

10/10 Excellent

"Nice modern motel well located for AT hike"

Jiminy Peak Mountain Resort

8/10 Good

"The rooms are outdated but they were clean. The hot tubs were down unfortunately which was one reason we booked this resort so that was a bummer but the staff was great and the price was right. The views were gorgeous and it's near hiking trails and a bike trail. Would book it again if they update their rooms and amenities."

Berkshires Untold

10/10 Excellent

"The lobby was absolutely beautiful, aesthetically and structurally! From all the greenery from the plants to the high ceilings, cute seating areas, and nice bar. The outdoor furniture was a plus, especially with the fire pits and the surrounded by the nice view of the berkshires. After an evening out, we came back and played a board game in the lobby and even did a little painting of our own while enjoying some good cocktails…you can definitely create a vibe. The room was clean, and overall it was a great stay if you’re just looking to relax, unwind, and get away for a bit!"

Berkshire Mountain Lodge

10/10 Excellent

"We've stayed at Berkshire Mountain Lodge in October a number of times now, and we really enjoy the property. The rooms are well-appointed, very clean, and quite comfortable. We appreciate the free washers and dryers as well as the many other amenities, and you cannot beat the location. There's a supermarket down the driveway and across the street and an excellent specialty grocer--Guido's Market--just down the road. We highly recommend this property. The District Restaurant in Pittsfield is excellent. We've also seen several great plays at Barrington Theatre Company. The area is loaded with historical and cultural activities. We like the proximity to Lenox and the Edith Wharton mansion as well as The Clark art museum in Williamstown, both of which have lovely grounds/gardens typically exhibiting sculptures. There are also abundant outdoor activities and opportunities for hiking and lovely scenic drives. This was a good year for fall color, and the red maples were glorious! It's a short ride to Vermont where we checked out Mt. Equinox for the first time. Highly recommend the drive to the top on a sunny, clear day."

Find out more about Cheshire

Cheshire B&B information

Number of reviews	3,042
Accommodation	46 B&B
Lowest Price	AU$161
Highest Price	AU$610

Frequently asked questions

Searching for B&Bs in Cheshire?

If you want to find some accommodation with fewer rooms than the traditional hotel and an intimate environment, a B&B might be a great fit for your trip to Cheshire. When you want to explore some attractions in town, Mount Greylock State Reservation and Cheshire Reservoir are worth a stop.

Why should you consider a B&B versus a traditional hotel?

B&Bs all have a unique charm — whether it's a cosy reading space or a beautiful breakfast room, the quaint details are what make bed and breakfasts the perfect escape.

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 decor. The Cornell Inn, Lenox & The Berkshires: 14.8 mi (23.9 km) from the city centre. Enjoy the free full breakfast and unique decor. 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 decor and patio area.

When is the best time 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 temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Cheshire are January, March, February and November, with each month seeing an average of 17 cm 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 such as 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) from the city centre. Otherwise, look 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.

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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. UU Rowe Camp and Conference Center

5. Shaker Mill Inn

6. Whistler's Inn Bed & Breakfast

7. Cozy Farmhouse Retreat - Ram Dass Room

8. Inn at Silver Maple Farm

9. Cozy Retreat in historic Farmhouse - Tranquility Room

10. The Red Door B&B

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

12. Chambery Inn

13. Brook Farm Inn

14. The Inn at Stockbridge

15. Devonfield Inn B&B

16. Experience Timeless Elegance in The Edith Wharton Room!

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

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

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

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

Top Cheshire Hotel Reviews

Quality Inn Lee - Lenox South

Jiminy Peak Mountain Resort

Berkshires Untold

Berkshire Mountain Lodge

The Whitlock

The Yankee Inn

The Cornell Inn, Lenox & The Berkshires

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Williams Inn

Find out more about Cheshire

Cheshire B&B information

Frequently asked questions

Explore a world of travel with Expedia

Search Cheshire Bed & 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. The Cornell Inn, Lenox & The Berkshires

4. UU Rowe Camp and Conference Center

5. Shaker Mill Inn

6. Whistler's Inn Bed & Breakfast

7. Cozy Farmhouse Retreat - Ram Dass Room

8. Inn at Silver Maple Farm

9. Cozy Retreat in historic Farmhouse - Tranquility Room

10. The Red Door B&B

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

12. Chambery Inn

13. Brook Farm Inn

14. The Inn at Stockbridge

15. Devonfield Inn B&B

16. Experience Timeless Elegance in The Edith Wharton Room!

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

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

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

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

Top Cheshire Hotel Reviews

Quality Inn Lee - Lenox South

Find out more about Cheshire

Cheshire B&B information

Frequently asked questions

Explore a world of travel with Expedia