A lake surrounded by autumn-colored trees and hills.

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Check prices for these dates

Next weekend
24 Jul - 26 Jul
In two weeks
31 Jul - 2 Aug
In one month
14 Aug - 16 Aug
In two months
11 Sept - 13 Sept

Our top choices for Cheshire bed & breakfast

Exterior

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (55 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is £180
includes taxes & fees
28 Jul - 29 Jul
Harbour House Inn
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (464 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is £142
includes taxes & fees
22 Jul - 23 Jul
Shaker Mill Inn
Property grounds

Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (505 reviews)
"Beautiful inn with the most interesting treasures and decorations."
United States
Mary
The price is £139
includes taxes & fees
20 Jul - 21 Jul
Whistler's Inn Bed & Breakfast
Terrace/patio

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, (151 reviews)
"Incredible staff, free parking and cute rooms!"
Canada
Priscilla
The price is £179
includes taxes & fees
19 Jul - 20 Jul
The Trail in Adams - Berkshires’ Art Hotel
Aerial view

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (112 reviews)
"Very nice hotel."
United States
Erdem
The price is £173
includes taxes & fees
22 Jul - 23 Jul
Inn at Silver Maple Farm
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"The staff were super friendly"
United States
John
The price is £140
includes taxes & fees
22 Jul - 23 Jul
The Cornell Inn, Lenox & The Berkshires
Suite, Private Bathroom (RedBird Suite) | View from room

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, (113 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is £295
includes taxes & fees
5 Aug - 6 Aug
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (381 reviews)
"Location is convenient to walk through downtown Lee and to get to a show at Tanglewood."
United States
Joseph
The price is £223
includes taxes & fees
23 Jul - 24 Jul
Chambery Inn
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (99 reviews)
"Great spot close to town. Cozy, tasteful, comfortable room. Nice breakfasts and pleasant interaction with the staff. We love the Berkshires and we’ll definitely stay here again."
United States
Stephen
The price is £321
includes taxes & fees
29 Jul - 30 Jul
The Inn at Stockbridge
Front of property – evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (139 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is £364
includes taxes & fees
21 Jul - 22 Jul
Devonfield Inn B&B
Luxury Room, 1 King Bed, Bathtub | Premium bedding, iron/ironing board, free WiFi, individually decorated

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is £577
includes taxes & fees
16 Aug - 17 Aug
33 Main
1 bedroom, WiFi, bed sheets

Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is £256
includes taxes & fees
22 Jul - 23 Jul
Experience Timeless Elegance in The Edith Wharton Room!
3 bedrooms, bed sheets

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
The price is £255
includes taxes & fees
22 Jul - 23 Jul
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Interior

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 £485
includes taxes & fees
10 Aug - 11 Aug
Cozy Carriage House room with a double bed and private balcony
Terrace/patio

Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is £421
includes taxes & fees
3 Aug - 4 Aug
Historic Susan B. Anthony Room - Cozy & Charming Stay
Front of property

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (168 reviews)
"Lovely stay!"
United States
Jiacheng
The price is £189
includes taxes & fees
20 Jul - 21 Jul
Brook Farm Inn
Interior

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 £273
includes taxes & fees
19 Jul - 20 Jul
Elegant Carriage House room with a queen bed and private patio.
Fireplace

Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn

Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Lenox
The price is £447
includes taxes & fees
23 Jul - 24 Jul
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
1 bedroom, bed sheets

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

Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Lenox
The price is £373
includes taxes & fees
23 Jul - 24 Jul
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
1 bedroom, bed sheets

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
The price is £473
includes taxes & fees
29 Jul - 30 Jul
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"The AC went out on my last night. That was the killer. But the pool, game room, and everything else was alright."
Owen 2-night trip
Posted 8 hours ago
Vacation Village in the Berkshires

Find out more about Cheshire

Cheshire B&B information

Number of reviews
3,094
Accommodation
46 B&B
Lowest Price
£139
Highest Price
£577

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. Chambery Inn: 9 rooms. 18.1 mi (29.1 km) from the city centre. Enjoy the private garden and snack bar/deli. Inn at Silver Maple Farm: 11 rooms. Located 18.2 mi (29.3 km) from the core of Cheshire. Enjoy the free buffet breakfast and designer toiletries.
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 Susan B. Anthony Birthplace Museum 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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