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Check prices for these dates

Next weekend
12 Jun - 14 Jun
In two weeks
19 Jun - 21 Jun
In one month
3 Jul - 5 Jul
In two months
31 Jul - 2 Aug

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, (53 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is ₹23,377
₹24,710 total
includes taxes & fees
1 Jul - 2 Jul
Harbour House Inn
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (458 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is ₹12,967
₹14,225 total
includes taxes & fees
4 Jun - 5 Jun
Shaker Mill Inn
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 ₹16,980
₹18,967 total
includes taxes & fees
8 Jun - 9 Jun
The Trail in Adams - Berkshires’ Art Hotel
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
"Great place, nice amenities and convenient location, highly recommended."
United States
Arthur
The price is ₹14,346
₹16,506 total
includes taxes & fees
3 Jun - 4 Jun
The Cornell Inn, Lenox & The Berkshires
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (377 reviews)
"Yes the room was spotless and always the staff is ready to answer any questions that we might have. We have been enjoying the Chambery Inn for many years always had a great stay and again looking for our next visit. Vincent Farricielli and Roibert Modena. "
United States
robert
The price is ₹16,245
₹18,145 total
includes taxes & fees
3 Jun - 4 Jun
Chambery Inn
Front of property – evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (138 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is ₹32,203
₹35,971 total
includes taxes & fees
8 Jun - 9 Jun
Devonfield Inn B&B
Property grounds

Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (501 reviews)
"This family owned Inn is absolutely charming and the owners are so nice! I will definitely stay here again when I visit the Berkshires."
United States
Stacey
The price is ₹25,314
₹28,276 total
includes taxes & fees
7 Jun - 8 Jun
Whistler's Inn Bed & Breakfast
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi

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 ₹55,744
₹62,266 total
includes taxes & fees
3 Jun - 4 Jun
33 Main
Front of property

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (164 reviews)
"Everything was perfect - location and accommodation."
United States
Christopher
The price is ₹14,783
₹17,273 total
includes taxes & fees
30 Jun - 1 Jul
Brook Farm Inn
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, (111 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is ₹31,365
₹37,942 total
includes taxes & fees
23 Jun - 24 Jun
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Lobby

Inn at Kenmore Hall

Inn at Kenmore Hall
3.0 star property
Richmond
10.0 out of 10, Exceptional, (28 reviews)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is ₹40,376
₹44,293 total
includes taxes & fees
16 Jun - 17 Jun
Inn at Kenmore Hall
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

Berkshires Untold

Berkshires Untold

10/10 Excellent
"Very nice hotel. Highly recommend the restaurant."
Thomas 2-night trip
Posted 1 hour ago
Berkshires Untold

Find out more about Cheshire

Cheshire B&B information

Number of reviews
2,417
Accommodation
23 B&B
Lowest Price
₹14,225
Highest Price
₹62,266

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 of the destination's attractions, Mount Greylock State Reservation is worth a visit.
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 explore some things to do in Cheshire, consider a visit to Mount Greylock State Reservation. You might also consider a trip to sites such as Mount Greylock State Reservation Visitor Center or Adams Theater 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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