The road less traveled sometimes is absolutely beautiful. In a month this will be a great spot for Autumn. I will repost the exact same foliage shot and see if I am correct. Excited to do it actually..

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B&B in Cheshire

"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."

￥26,701 total

includes taxes & fees

Sep 1 - Sep 2

"Nice unique design. A very nice seating area in the living room. The bedroom nicely arranged, fully stocked with all items one needs for the stay, and very clean. A beautiful warm breakfast and access 24/7 to a full kitchen. "

￥30,981 total

includes taxes & fees

Sep 8 - Sep 9

"Very casual and easy check in and out; lovely and substantial breakfast"

￥26,545 total

includes taxes & fees

Aug 26 - Aug 27

"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "

￥36,666 total

includes taxes & fees

Sep 9 - Sep 10

"We returned to the Chambery Inn to celebrate my wife's birthday and the Memorial Day weekend. We were very happy with our choice. We stayed in a beautiful room (203), which included a spacious sitting area and a well-appointed bath. The breakfast were nicely prepared and presented. The Inn provided timely information prior and during our stay. We will be back in the future. "

"Very enjoyable comfortable stay"

"Nice quaint out of the ordinary vacation experience. "

￥26,856 total

includes taxes & fees

Aug 25 - Aug 26

Loft, Private Bathroom (Skylight Loft) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds

"Inn was gorgeous and staff exceptional!"

Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi

"33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! "

￥92,455 total

includes taxes & fees

Aug 26 - Aug 27

1 bedroom, bed sheets, wheelchair access

￥44,217 total

includes taxes & fees

Sep 1 - Sep 2

2 Bedrooms 1 Bath | 1 bedroom, premium bedding, iron/ironing board, free WiFi

"The owner did not honor our confirmed Expedia reservation, so we had to find a hotel at the last minute. She made up various excuses and was very rude."

￥39,527 total

includes taxes & fees

Aug 25 - Aug 26

￥50,127 total

includes taxes & fees

Sep 1 - Sep 2

￥44,217 total

includes taxes & fees

Sep 1 - Sep 2

￥47,170 total

includes taxes & fees

Sep 3 - Sep 4

￥53,080 total

includes taxes & fees

Sep 1 - Sep 2

￥67,196 total

includes taxes & fees

Sep 1 - Sep 2

￥73,268 total

includes taxes & fees

Sep 7 - Sep 8

￥82,132 total

includes taxes & fees

Sep 2 - Sep 3

￥82,132 total

includes taxes & fees

Sep 1 - Sep 2

"Great breakfast, friendly helpful staff, pretty yard, good location "

￥55,012 total

includes taxes & fees

Sep 8 - Sep 9

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Top Cheshire Hotel Reviews

The Yankee, Trademark Collection by Wyndham

10/10 Excellent

"Great option a little further away from Lenox! Clean and great service. "

The Constance by the Lenox Collection

10/10 Excellent

"The staff on duty were very professional and pleasant. The young man on duty on Thursday afternoon and evening was very attentive and capably answered my question about the Shakespeare theater. My room was very clean and modern. The slight problem with the bed footboard did not effect my comfort or the function of the bed."

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent

"This place is it's own oasis in the Berkshires. Very nice place which was clean and the folks we talked to at the front desk were very very nice and helpful! It would be tough for someone who has any mobility issues, no elevator and even we had a really hard time getting into and out of the tub/shower and we don't have mobility issues."

Vacation Village in the Berkshires

10/10 Excellent

"Staff was pleasant and helpful, apartment was spacious and clean. For about the same price as a hotel room, we had a 1 bedroom apartment with a ptl. kitchen (full size fridge with freezer, microwave, 2 burner cooktop, large sink) and resort amenities (indoor, outdoor and kid's pool and a hot tub) and activities. "

Find out more about Cheshire

Cheshire B&B information

Number of reviews	2,706
Accommodation	23 B&B
Lowest Price	￥18,761
Highest Price	￥82,771

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Frequently asked questions

Searching for B&Bs in Cheshire?

If you want to find a place to stay with a small number of rooms and a more personalized environment, a B&B might be a great fit for your vacation to Cheshire. If your ideal vacation to Cheshire includes spending lots of time outside, Mount Greylock State Reservation is a good spot to enjoy the scenery.

Why would you choose a B&B versus a traditional hotel?

B&Bs all have a unique charm. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a fun place to get away.

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 décor. The Cornell Inn, Lenox & The Berkshires: 14.8 mi (23.9 km) from the downtown core. Enjoy the free full breakfast and unique décor. Chambery Inn: 9 rooms. Situated 18.1 mi (29.1 km) from the heart of Cheshire. Enjoy the private yard and deli. Whistler's Inn Bed & Breakfast: 14 rooms. 15.1 mi (24.2 km) from the heart of downtown. Enjoy the private yard and unique décor.

What's the best time of year 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 temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Cheshire are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

What is there to do in Cheshire?

When you want to check out 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 like 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) away from the heart of the city. You can also search 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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Find Cheshire Bed And Breakfast

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Treat yourself

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Check prices for these dates

B&B in Cheshire

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel

Shaker Mill Inn

Shaker Mill Inn

Harbour House Inn

Harbour House Inn

Chambery Inn

Chambery Inn

Devonfield Inn B&B

Devonfield Inn B&B

Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast

Brook Farm Inn

Brook Farm Inn

33 Main

33 Main

Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!

Tanglewood Suites

Tanglewood Suites

Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony

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

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

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

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

Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay

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

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

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & 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

Elegant suite with a king bed, fireplace, and kitchenette.

Elegant suite with a king bed, fireplace, and kitchenette.

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

Top Cheshire Hotel Reviews

The Yankee, Trademark Collection by Wyndham

Find out more about Cheshire

Find out more about Cheshire

Cheshire B&B information

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