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

Our top choices for Cheshire bed & breakfast

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

₩234,881 total

includes taxes & fees

Sep 22 - Sep 23

"This family owned Inn is absolutely charming and the owners are so nice! I will definitely stay here again when I visit the Berkshires."

₩218,538 total

includes taxes & fees

Sep 22 - Sep 23

"What a wonderful one-night stay on the July 4th weekend. It’s a beautiful, comfortable inn with lovely hosts. Also in a great location, set back from a fairly busy country road with several good food options nearby, and charming villages and towns to tour. Highly recommend. "

₩324,940 total

includes taxes & fees

Sep 21 - Sep 22

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

₩261,924 total

includes taxes & fees

Sep 22 - Sep 23

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

"NOT A REAL LOCATION. There was nothing there. Neighbors said this was a scam. Expedia ended up helping us find a local hotel room though the location was not as good. DO NOT BOOK THIS LOCATION -- it needs to be taken off the website."

₩373,415 total

includes taxes & fees

Sep 20 - Sep 21

"We had an excellent experience. The location was convenient for our needs, clean, and tastefully done. It's excellent value for the area. It must be said that a younger traveller will probably be more comfortable with the low-touch approach (text check in, code-locked doors), but they've clearly made an effort to be more accessible to a traveler looking for something more traditional. "

₩269,413 total

includes taxes & fees

Sep 22 - Sep 23

"ease of late check in. Super comfortable room."

₩348,864 total

includes taxes & fees

Sep 21 - Sep 22

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

"Inn was gorgeous and staff exceptional!"

₩278,395 total

includes taxes & fees

Sep 24 - Sep 25

"A great getaway! Everything was excellent!"

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

₩519,696 total

includes taxes & fees

Oct 6 - Oct 7

"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!! "

₩384,869 total

includes taxes & fees

Sep 23 - Sep 24

"The inn has an excellent location and amenities."

₩556,818 total

includes taxes & fees

Sep 28 - Sep 29

"This is a beautiful property straight out of a magazine. Service was impeccable"

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! "

₩959,649 total

includes taxes & fees

Oct 8 - Oct 9

"Dahlia is great. Excellent accommodation. We walked to Tanglewood "

Comfort Apartment, 1 Bedroom, Mountain View, Garden Area | Private kitchenette | Mini-fridge, paper towels

"GORGEOUS Scenery and NICE place to stay !"

"Well-run and elegant property. "

₩623,118 total

includes taxes & fees

Sep 21 - Sep 22

"Centrally located. Lovely hosts. Only three bedrooms so we got to know the other guests. The breakfasts were works of art as well as delicious."

"Very convenient location to arts / outdoors events in Lenox area. Available for one night stay, last minute booking. Host very responsive"

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Top Cheshire Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"No food, no parking near…"

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent

"Valerie at the front desk and who checked me in was above and beyond in customer service. She checked to see if I had a IGH account—which I did but had forgotten, and reminded me about the points and promotions. This Holiday Inn is a well managed property. Thank you"

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

10/10 Excellent

"We stayed for 5 nights and really enjoyed the surroundings and the drive to the property. The area is peaceful and quiet, with plenty to do for kids, including a mountain hike that even our 2- and 6-year-olds managed well. The grounds are beautiful for photos, very well maintained, and we often saw the crew cleaning and painting the sidewalks. I booked 2 suites, which were a good size for a family of four and offered plenty of space. The only downsides were that check-in felt a bit tedious it took several tries to swipe my card and there was no housekeeping service or follow-up to check on amenities during our stay. A self check-in option would make things smoother. Overall, we loved the quietness, the family-friendly activities, and the clean, well-kept property. With a few improvements in guest service, this could easily be a 5-star experience."

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

10/10 Excellent

" To whom it may concern, My wife & I were blessed beyond measures with Chris the recepcionista who was an amazing incredible human being who treated us like family. We needed some direction to southbridge Ma. He explain to us the best way to get there and back to the hotel. Also the other gentleman working along side of him also assisted us as well. Thank you for this beautiful experience and to let you know that we will come again. Please give our love to the precious lady housekeeper who blessed us as well. "

Find out more about Cheshire

Cheshire B&B information

Number of reviews	2,739
Accommodation	23 B&B
Lowest Price	₩218,538
Highest Price	₩959,649

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. When you want to explore some of the destination's attractions, Mount Greylock State Reservation is worth a visit.

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. Inn at Silver Maple Farm: 11 rooms. Situated 18.2 mi (29.3 km) from the heart of Cheshire. Enjoy the free buffet breakfast and designer toiletries.

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 explore some things to do in Cheshire, consider a visit to Mount Greylock State Reservation. 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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Search B&B in Cheshire

Change your mind

Treat yourself

Be picky

Check prices for these dates

B&B in Cheshire

Our top choices for Cheshire bed & breakfast

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast

Inn at Silver Maple Farm

Inn at Silver Maple Farm

Shaker Mill Inn

Shaker Mill Inn

Tanglewood Suites

Tanglewood Suites

The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel

Chambery Inn

Chambery Inn

Brook Farm Inn

Brook Farm Inn

Lakehouse Inn

Lakehouse Inn

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

Harbour House Inn

Harbour House Inn

Devonfield Inn B&B

Devonfield Inn B&B

Inn at Kenmore Hall

Inn at Kenmore Hall

33 Main

33 Main

Eastgate Inn B&B

Eastgate Inn B&B

Berkshire Mountain House

Berkshire Mountain House

The Inn at Stockbridge

The Inn at Stockbridge

The Red Door B&B

The Red Door B&B

UU Rowe Camp and Conference Center

UU Rowe Camp and Conference Center

Chesapeake Inn of Lenox

Chesapeake Inn of Lenox

Top Cheshire Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

Find out more about Cheshire

Find out more about Cheshire

Cheshire B&B information

Frequently asked questions

Explore a world of travel with Expedia

Explore a world of travel with Expedia

More Accommodation Types in Cheshire

All Accommodation Types

More ways to book