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

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Check prices for these dates

Next weekend
19 Jun - 21 Jun
In two weeks
26 Jun - 28 Jun
In one month
10 Jul - 12 Jul
In two months
7 Aug - 9 Aug

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 6.677.638 ₫
7.058.264 ₫ total
includes taxes & fees
24 Jun - 25 Jun
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 4.264.488 ₫
4.678.143 ₫ total
includes taxes & fees
17 Jun - 18 Jun
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 3.132.556 ₫
3.508.463 ₫ total
includes taxes & fees
23 Jun - 24 Jun
Inn at Silver Maple Farm
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 4.500.654 ₫
5.027.231 ₫ total
includes taxes & fees
18 Jun - 19 Jun
Chambery Inn
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 4.968.655 ₫
5.549.987 ₫ total
includes taxes & fees
15 Jun - 16 Jun
The Trail in Adams - Berkshires’ Art Hotel
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 8.660.596 ₫
9.673.807 ₫ total
includes taxes & fees
14 Jun - 15 Jun
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 9.837.474 ₫
11.538.073 ₫ total
includes taxes & fees
25 Jun - 26 Jun
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 4.392.448 ₫
5.053.554 ₫ total
includes taxes & fees
23 Jun - 24 Jun
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 5.069.425 ₫
5.662.700 ₫ total
includes taxes & fees
18 Jun - 19 Jun
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 18.293.621 ₫
20.433.975 ₫ total
includes taxes & fees
25 Jun - 26 Jun
33 Main
Front of property

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (165 reviews)
"Lovely stay!"
United States
Jiacheng
The price is 4.956.546 ₫
5.747.056 ₫ total
includes taxes & fees
1 Jul - 2 Jul
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.
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Top Cheshire Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Clean kitchen and room over-all. Accessories in kitchen were adequate. Like that room is not cleaned every day."
Douglas 3-night trip
Posted 7 hours ago
Berkshire Mountain Lodge

Find out more about Cheshire

Cheshire B&B information

Number of reviews
2,629
Accommodation
23 B&B
Lowest Price
3.508.463 ₫
Highest Price
20.433.975 ₫

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. When you want to explore some of the destination's attractions, Mount Greylock State Reservation is worth a visit.
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, March, February and November, with each month seeing an average of 17 cm 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 such as 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) 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.

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