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Featured B&B in Cheshire

The Cornell Inn, Lenox
3.0 star property
8.8 out of 10, Excellent, 1,002 reviews
"The staff was very friendly and the breakfast was delicious. The outdoor areas were beautiful. The room was beautifully designed"
The price is RM 551
per night
4 Jun - 5 Jun
The Cornell Inn, Lenox
Lakehouse Inn
4.0 star property
9.6 out of 10, Exceptional, 155 reviews
"They greeted us as soon as we checked in with apple cider and brownies. The room was super cute. Breakfast was delicious. The only negative was it could be noisy when people are walking in hallway. We will definitely stay again. "
The price is RM 621
per night
4 Jun - 5 Jun
Lakehouse Inn
Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, 136 reviews
"This is a charming and very pleasant place to stay."
The price is RM 946
per night
4 Jun - 5 Jun
Brook Farm Inn
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Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, 386 reviews
"Quaint "
The price is RM 618
per night
4 Jun - 5 Jun
Shaker Mill Inn
Inn at Silver Maple Farm
3.0 star property
9.8 out of 10, Exceptional, 68 reviews
"Clean! Innkeepers were professional and accommodating. Great breakfasts!"
The price is RM 795
per night
4 Jun - 5 Jun
Inn at Silver Maple Farm
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, 356 reviews
"Amazing place.."
The price is RM 1,172
per night
6 Jun - 7 Jun
Chambery Inn
33 Main
4.0 star property
10.0 out of 10, Exceptional, 63 reviews
"I love the fact that it only had eight rooms they had happy hour from 5 to 6 PM so we are able to meet other people at the hotel. I love the rooms and the cleanliness and especially the breakfast they were amazing and delicious!! I would recommend this hotel highly!"
The price is RM 1,821
per night
5 Jun - 6 Jun
33 Main
The Inn at Stockbridge
4.0 star property
9.6 out of 10, Exceptional, 94 reviews
"Fantastic!"
The Inn at Stockbridge
Whistler's Inn Bed & Breakfast
3.5 star property
7.6 out of 10, Good, 433 reviews
"Gorgeous loved large home where you will feel at home. Lots of antiques, books. Grand piano. Hosts very welcoming. No air conditioning. Hot showers once hot water heater turned on. First night unfortunately cool shower. Dog friendly. Breakfast choice fine. So near to Lennox (easy walk downhill) and close to Tanglewood. Really comfortable beds. This is an old house built in 1867 and there are many ongoing minor repairs to do with walls. Highly recommend and looking forward to returning. "
The price is RM 640
per night
17 Jun - 18 Jun
Whistler's Inn Bed & Breakfast
The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
8.8 out of 10, Excellent, 105 reviews
"It was clean and quiet good Breakfast "
The price is RM 1,030
per night
4 Jun - 5 Jun
The Trail in Adams - Berkshires’ Art Hotel
Devonfield Inn B&B
4.0 star property
10.0 out of 10, Exceptional, 106 reviews
"The classic character of the Inn is so beautiful and adds to the whole experience!"
The price is RM 1,737
per night
5 Jun - 6 Jun
Devonfield Inn B&B
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
9.2 out of 10, Wonderful, 101 reviews
"The b&b was so beautiful and unique! The area was serene. The host was very sweet and accommodating."
The price is RM 2,160
per night
4 Jun - 5 Jun
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Inn at Kenmore Hall
3.0 star property
10.0 out of 10, Exceptional, 25 reviews
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
Inn at Kenmore Hall
Berkshire Mountain House
3.0 star property
9.4 out of 10, Exceptional, 22 reviews
"GORGEOUS Scenery and NICE place to stay !"
Berkshire Mountain House
Tanglewood Suites
2.5 star property
8.0 out of 10, Very good, 15 reviews
"The property is so lovely and peaceful. I love the classic mid-century modern aesthetic. For visitors to the National Shrine of Divine Mercy, the Inn’s location couldn’t be more perfect with only a 5-minute walk to the Shrine. "
Tanglewood Suites
Harbour House Inn
3.5 star property
9.4 out of 10, Exceptional, 48 reviews
"Decorations were beautiful, room and bed were so comfortable, hostess and food were wonderful. Brandi was thoughtful in every way possible. Can't go wrong choosing this place over a chain. Love it!"
The price is RM 1,164
per night
10 Jun - 11 Jun
Harbour House Inn
Eastgate Inn B&B
2.5 star property
9.0 out of 10, Wonderful, 64 reviews
"The owner, Daliya, is very friendly and helpful, with good advice. We enjoyed the breakfasts."
Eastgate Inn B&B
The Red Door B&B
3.0 star property
10.0 out of 10, Exceptional, 5 reviews
"We loved staying at this b&b. The owners were very accommodating, kind and helpful. Because of the pandemic, they only took us for the weekend. The breakfasts were above and beyond our expectations, simply fantastic. We highly recommend this beautiful place and we will be back for sure. "
The Red Door B&B
Chesapeake Inn of Lenox
3.0 star property
7.2 out of 10, Good, 8 reviews
"Very convenient location to arts / outdoors events in Lenox area. Available for one night stay, last minute booking. Host very responsive"
Chesapeake Inn of Lenox
Federal House Inn
3.5 star property
9.0 out of 10, Wonderful, 406 reviews
"Beautiful old house. Personable, helpful and accommodating staff. Wonderful homemade breakfast, wine hour and snacks. We had a great stay."
Federal House Inn
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See all available properties in Cheshire
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.

Other property types in Cheshire

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, 858 reviews
"Staff were so attentive, even at the late hour we checked in (10pm) the place had everything you need. Amazing views and amenities. Loved it"
The price is RM 748
per night
4 Jun - 5 Jun
Jiminy Peak Mountain Resort
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.

Cheshire B&B information

Number of reviews
2,530
Accommodation
20 B&B
Lowest Price
RM551
Highest Price
RM2,278

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. If your ideal holiday to Cheshire includes spending lots of time outside, Mount Greylock State Reservation is a good spot to enjoy the scenery.
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.
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, April, March and February, with each month seeing an average of 20 cm of snowfall.
What is there to do in Cheshire?
When you want to see some attractions in town, you might consider a visit to Mount Greylock State Reservation and St Mary’s of the Assumption Church. 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.

Recent Reviews in Cheshire
Expedia verified reviews