A lake surrounded by autumn-colored trees and hills.

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Check prices for these dates

Next weekend
7 Aug - 9 Aug
In two weeks
14 Aug - 16 Aug
In one month
28 Aug - 30 Aug
In two months
25 Sep - 27 Sep

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, (55 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is 6.678.399 ₫
7.059.067 ₫ total
includes taxes & fees
28 Jul - 29 Jul
Harbour House 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, (152 reviews)
"Incredible staff, free parking and cute rooms!"
Canada
Priscilla
The price is 5.133.180 ₫
5.733.761 ₫ total
includes taxes & fees
29 Jul - 30 Jul
The Trail in Adams - Berkshires’ Art Hotel
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"The cornel Inn is terrific! Great location near tanglewood, shops snd restaurants. Great breakfast"
United States
Judith
The price is 4.330.193 ₫
4.981.931 ₫ total
includes taxes & fees
29 Jul - 30 Jul
The Cornell Inn, Lenox & The Berkshires
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (465 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is 5.212.152 ₫
5.717.731 ₫ total
includes taxes & fees
29 Jul - 30 Jul
Shaker Mill Inn
Property grounds

Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (507 reviews)
"Beautiful inn with the most interesting treasures and decorations."
United States
Mary
The price is 4.477.712 ₫
5.001.823 ₫ total
includes taxes & fees
29 Jul - 30 Jul
Whistler's Inn Bed & Breakfast
Aerial view

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (112 reviews)
"Very nice hotel."
United States
Erdem
The price is 6.028.196 ₫
6.751.580 ₫ total
includes taxes & fees
24 Aug - 25 Aug
Inn at Silver Maple Farm
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (383 reviews)
"Location is convenient to walk through downtown Lee and to get to a show at Tanglewood."
United States
Joseph
The price is 7.107.217 ₫
7.938.792 ₫ total
includes taxes & fees
26 Aug - 27 Aug
Chambery Inn
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (99 reviews)
"Beautifully decorated inside and gorgeous gardens and landscaping outside. A lovely serene spot away from the crowds that are only minutes away in downtown Stockbridge. The breakfasts were plentiful, artfully presented and delicious. Staff were friendly and very competent."
United States
Barbara
The price is 9.760.939 ₫
11.448.307 ₫ total
includes taxes & fees
29 Jul - 30 Jul
The Inn at Stockbridge
Front of property – evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (139 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is 11.556.236 ₫
12.908.237 ₫ total
includes taxes & fees
19 Aug - 20 Aug
Devonfield Inn B&B
Suite, Private Bathroom (RedBird Suite) | View from room

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
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (113 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is 8.691.395 ₫
10.514.065 ₫ total
includes taxes & fees
9 Aug - 10 Aug
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Luxury Room, 1 King Bed, Bathtub | Premium bedding, iron/ironing board, free WiFi, individually decorated

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (75 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is 19.693.511 ₫
21.997.652 ₫ total
includes taxes & fees
16 Aug - 17 Aug
33 Main
Front of property

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (169 reviews)
"Lovely stay!"
United States
Jiacheng
The price is 6.407.788 ₫
7.368.088 ₫ total
includes taxes & fees
3 Aug - 4 Aug
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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"I love the Red Lion Inn because of its Old World charm. My husband thinks it could use some new rugs and fix cracked ceiling, but that does not bother me in the least. I just enjoy the place, including the dining room. Our room was very large and comfortable and very clean---no complaints at all. We have been there in the past and will be there again."
Sandra 3-night trip
Posted 1 hour ago
The Red Lion Inn

Find out more about Cheshire

Cheshire B&B information

Number of reviews
1,227
Accommodation
23 B&B
Lowest Price
4.981.931 ₫
Highest Price
21.997.652 ₫

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 attractions in town, Mount Greylock State Reservation and Cheshire Reservoir are worth a stop.
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 spend some time in the great outdoors, Mount Greylock State Reservation and Cheshire Reservoir are some notable spots. You might also consider a trip to sites such as Mount Greylock State Reservation Visitor Center or Susan B. Anthony Birthplace Museum 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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