Photo by Ed Gaffny

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"The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!"

per night

23 Jun - 24 Jun

"I really loved my stay at this beautiful property surrounded by nature and peacefulness in the Berkshire mountains. The owners were great too with communication and making things easy for check in and check out. Highly recommend this place!"

"The house was clean and cozy. The kitchen was well stocked, especially important as we like to cook at home. Justin was responsive when I contacted him with questions. Love that the house was dog friendly with a fenced in back yard. The house has been updated inside but the deck needs some TLC, which I am sure are in the plans. A perfect get away!"

Cheshire B&B information

Number of reviews	2,358
Accommodation	27 B&B
Lowest Price	£116
Highest Price	£1,026

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.