An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.

Search B&B in Cheshire

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Jun 26 - Jun 28
In two weeks
Jul 3 - Jul 5
In one month
Jul 17 - Jul 19
In two months
Aug 14 - Aug 16

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 NT$8,005
NT$8,462 total
includes taxes & fees
Jun 22 - Jun 23
Harbour House Inn
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (461 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is NT$4,702
NT$5,158 total
includes taxes & fees
Jun 17 - Jun 18
Shaker Mill Inn
Aerial view

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (107 reviews)
"Very nice hotel."
United States
Erdem
The price is NT$5,964
NT$6,679 total
includes taxes & fees
Jun 22 - Jun 23
Inn at Silver Maple Farm
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 NT$6,247
NT$6,978 total
includes taxes & fees
Jun 22 - Jun 23
The Trail in Adams - Berkshires’ Art Hotel
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (378 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 NT$5,395
NT$6,027 total
includes taxes & fees
Jun 17 - Jun 18
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 NT$10,697
NT$11,948 total
includes taxes & fees
Jun 17 - Jun 18
Devonfield Inn B&B
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Great spot close to town. Cozy, tasteful, comfortable room. Nice breakfasts and pleasant interaction with the staff. We love the Berkshires and we’ll definitely stay here again."
United States
Stephen
The price is NT$11,793
NT$13,832 total
includes taxes & fees
Jun 23 - Jun 24
The Inn at Stockbridge
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,003 reviews)
"Great place, nice amenities and convenient location, highly recommended."
United States
Arthur
The price is NT$5,279
NT$6,073 total
includes taxes & fees
Jun 21 - Jun 22
The Cornell Inn, Lenox & The Berkshires
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 NT$5,907
NT$6,598 total
includes taxes & fees
Jun 18 - Jun 19
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 NT$21,931
NT$24,497 total
includes taxes & fees
Jun 17 - Jun 18
33 Main
Front of property

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (167 reviews)
"Lovely stay!"
United States
Jiacheng
The price is NT$5,787
NT$6,716 total
includes taxes & fees
Jun 17 - Jun 18
Brook Farm Inn
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cheshire Hotel Reviews

Hotel On North

Hotel On North

10/10 Excellent
"The whole experience was great. Staff excellent."
Pamela 1-night trip
Posted 2 hours ago
Hotel On North

Find out more about Cheshire

Cheshire B&B information

Number of reviews
Accommodation
 B&B
Lowest Price
Highest Price

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. Chambery Inn: 9 rooms. 18.1 mi (29.1 km) from the heart of downtown. Enjoy the private yard and deli. The Trail in Adams - Berkshires' Art Hotel: 9 rooms. Located 4.7 mi (7.5 km) from the core of Cheshire. Enjoy the unique décor and patio area.
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 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) 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.

Explore a world of travel with Expedia