A lake surrounded by autumn-colored trees and hills.

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Check prices for these dates

Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct
In one month
30 Oct - 1 Nov
In two months
27 Nov - 29 Nov

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

Harbour House Inn
3.5 star property
Cheshire
9.6 out of 10, Exceptional, (58 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is HK$1,991
HK$2,104 total
includes taxes & fees
26 Oct - 27 Oct
Harbour House Inn
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

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
9.0 out of 10, Wonderful, (157 reviews)
"Fun decor, friendly staff, great complimentary breakfast, directly on bike path."
United States
Susan
The price is HK$1,364
HK$1,523 total
includes taxes & fees
1 Nov - 2 Nov
The Trail in Adams - Berkshires’ Art Hotel
A snow-covered outdoor area with a patio, seating, and a covered dining area.

3. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"Convenient location for Tanglewood and other Berkshire sights. Nice complimentary breakfast and arrival cocktail."
United States
Rosann
The price is HK$1,204
HK$1,381 total
includes taxes & fees
27 Oct - 28 Oct
The Cornell Inn, Lenox & The Berkshires
A house with a chimney, surrounded by trees with autumn foliage.

4. UU Rowe Camp and Conference Center

UU Rowe Camp and Conference Center
2.0 star property
Rowe
10.0 out of 10, Exceptional, (1 review)
"Yes"
United States
Stuart
The price is HK$1,052
HK$1,112 total
includes taxes & fees
25 Oct - 26 Oct
UU Rowe Camp and Conference Center
Room

5. Cozy Retreat in historic Farmhouse - Tranquility Room

Cozy Retreat in historic Farmhouse - Tranquility Room
Rowe
The price is HK$1,020
HK$1,186 total
includes taxes & fees
5 Oct - 6 Oct
Cozy Retreat in historic Farmhouse - Tranquility Room
A garden with a white gazebo, a brick pathway, and various plants and flowers.

6. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (519 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
The price is HK$1,157
HK$1,292 total
includes taxes & fees
5 Oct - 6 Oct
Whistler's Inn Bed & Breakfast
A red building with a sign reading "Shaker Mill Inn."

7. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (476 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is HK$1,091
HK$1,197 total
includes taxes & fees
3 Nov - 4 Nov
Shaker Mill Inn
A wooden deck with a table and chairs, surrounded by a metal railing, overlooking a lush green landscape with trees.

8. The Red Door B&B

The Red Door B&B
3.0 star property
Lee
10.0 out of 10, Exceptional, (5 reviews)
"Centrally located. Lovely hosts. Only three bedrooms so we got to know the other guests. The breakfasts were works of art as well as delicious."
United States
Anonymous traveller
The price is HK$1,377
HK$2,195 total
includes taxes & fees
26 Oct - 27 Oct
The Red Door B&B
An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

9. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (117 reviews)
"Very nice hotel."
United States
Erdem
The price is HK$1,601
HK$1,793 total
includes taxes & fees
1 Nov - 2 Nov
Inn at Silver Maple Farm
Room

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

Cozy Retreat in Historic Farmhouse, Charming Bunk Bed Room,- Owl Dorm
Rowe
10.0 out of 10, Exceptional, (2 reviews)
"The piano, large spaces, and fireplace were all much appreciated."
United States
Benjamin B.
The price is HK$1,020
HK$1,186 total
includes taxes & fees
4 Oct - 5 Oct
Cozy Retreat in Historic Farmhouse, Charming Bunk Bed Room,- Owl Dorm
Room

11. Cozy Farmhouse Retreat - Ram Dass Room

Cozy Farmhouse Retreat - Ram Dass Room
Rowe
The price is HK$706
HK$872 total
includes taxes & fees
4 Oct - 5 Oct
Cozy Farmhouse Retreat - Ram Dass Room
A two-story building with a sign reading "Chambéry Inn".

12. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (388 reviews)
"An absolutely perfect getaway spot! Beautiful rooms, great service, and an ideal location. Highly recommend and we will be going back."
United States
Alexandra
The price is HK$2,118
HK$2,366 total
includes taxes & fees
18 Oct - 19 Oct
Chambery Inn
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

13. Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (174 reviews)
"Breakfast was not only delicious, the room was sweet and bright and staff very attentive."
United States
Carrie
The price is HK$1,526
HK$1,768 total
includes taxes & fees
2 Nov - 3 Nov
Brook Farm Inn
A neatly made bed with a headboard, a bedside lamp, a framed painting, and a small bedside table with a tissue box.

14. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is HK$1,941
HK$2,524 total
includes taxes & fees
27 Oct - 28 Oct
Experience Timeless Elegance in The Edith Wharton Room!
A large, two-story house with a well-maintained lawn and a fence.

15. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (141 reviews)
"Wonderful location and hosts are amazing. Breakfast was great. Clean."
United States
Sebastien
The price is HK$2,896
HK$3,235 total
includes taxes & fees
2 Nov - 3 Nov
Devonfield Inn B&B
Front of property

16. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.6 out of 10, Exceptional, (107 reviews)
"Lovely grounds, property.. room was lovely. Delicious breakfast friendly helpful owners and staff great location"
United States
Jodi
The price is HK$2,863
HK$3,357 total
includes taxes & fees
1 Nov - 2 Nov
The Inn at Stockbridge
A two-story house with a brick entrance and a white facade.

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

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (119 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is HK$2,997
HK$3,626 total
includes taxes & fees
1 Nov - 2 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A well-appointed bedroom with a large bed, a bedside table, a chair, and a bathroom visible through an open door.

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
The price is HK$1,941
HK$2,524 total
includes taxes & fees
27 Oct - 28 Oct
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
A room with a dark green sofa, a small table with a vase of flowers, a desk with a lamp, and a window with curtains.

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

Elegant Carriage House room with a queen bed and private patio.
Lenox
The price is HK$3,008
HK$3,915 total
includes taxes & fees
20 Oct - 21 Oct
Elegant Carriage House room with a queen bed and private patio.
A porch with a white railing, a potted plant, and a view of a garden.

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

Cozy Carriage House room with a double bed and private balcony
Lenox
The price is HK$2,380
HK$3,090 total
includes taxes & fees
1 Nov - 2 Nov
Cozy Carriage House room with a double bed and private balcony
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cheshire Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

8/10 Good
"I have stayed here multiple times. My unit this trip was very clean, well equipped and comfortable. The check in process and front desk staff were terrific. My only issue was a strong smell of marijuana coming through the slider and bedroom window . The staff gave me a fan to blow the smell back out however it was an issue throughout my stay."
Susan 7-night trip
Posted 9 hours ago
Berkshire Mountain Lodge

Find out more about Cheshire

Cheshire B&B information

Number of reviews
2,626
Accommodation
46 B&B
Lowest Price
HK$872
Highest Price
HK$3,915

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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