A lake surrounded by autumn-colored trees and hills.

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Check prices for these dates

Next weekend
18 Sep - 20 Sep
In two weeks
25 Sep - 27 Sep
In one month
9 Oct - 11 Oct
In two months
6 Nov - 8 Nov

Our top choices for Cheshire bed & breakfast

Exterior

1. Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (56 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is ฿8,345
฿8,820 total
includes taxes & fees
10 Sept - 11 Sept
Harbour House Inn
Terrace/patio

2. 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, (156 reviews)
"Great central location for travelers there to see the sights."
United States
Jenna
The price is ฿5,676
฿6,340 total
includes taxes & fees
22 Sept - 23 Sept
The Trail in Adams - Berkshires’ Art Hotel
Exterior

3. 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)
"Lovely people and place. Breakfast was great and so was the room. Highly recommend."
United States
FRED
The price is ฿5,413
฿6,208 total
includes taxes & fees
13 Sept - 14 Sept
The Cornell Inn, Lenox & The Berkshires
Garden

4. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (471 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is ฿4,901
฿5,376 total
includes taxes & fees
10 Sept - 11 Sept
Shaker Mill Inn
Property grounds

5. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (517 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
The price is ฿5,834
฿6,517 total
includes taxes & fees
1 Oct - 2 Oct
Whistler's Inn Bed & Breakfast
Aerial view

6. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (116 reviews)
"We had a very pleasant stay at this. Eautiful country property. Check in was smooth and instructions were easy to follow. Our room, in the main building was well appointed. The bed was super comfortable and the amenities were fine. Breakfast was great! Common areas were lovely and inviting, and the s’mores kits in the lobby were just the thing for an evening around the outdoor fire pit. Highly recommend for anyone seeking a serene country setting."
United States
Jody
The price is ฿7,532
฿8,436 total
includes taxes & fees
10 Sept - 11 Sept
Inn at Silver Maple Farm
Front of property

7. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (387 reviews)
"An absolutely perfect getaway spot! Beautiful rooms, great service, and an ideal location. Highly recommend and we will be going back."
United States
Alexandra
The price is ฿8,881
฿9,920 total
includes taxes & fees
10 Sept - 11 Sept
Chambery Inn
Front of property – evening/night

8. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (140 reviews)
"Excellent food and helpful staff"
United States
Richard
The price is ฿13,453
฿15,027 total
includes taxes & fees
10 Sept - 11 Sept
Devonfield Inn B&B
Front of property

9. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (106 reviews)
"Lovely grounds, property.. room was lovely. Delicious breakfast friendly helpful owners and staff great location"
United States
Jodi
The price is ฿12,400
฿14,543 total
includes taxes & fees
14 Sept - 15 Sept
The Inn at Stockbridge
Suite, Private Bathroom (RedBird Suite) | View from room

10. 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, (117 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is ฿10,860
฿13,137 total
includes taxes & fees
28 Sept - 29 Sept
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property

11. Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (174 reviews)
"Breakfast was not only delicious, the room was sweet and bright and staff very attentive."
United States
Carrie
The price is ฿7,956
฿9,150 total
includes taxes & fees
10 Sept - 11 Sept
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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent
"Convenient location"
Peter 2-night trip
Posted 2 hours ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Find out more about Cheshire

Cheshire B&B information

Number of reviews
2,084
Accommodation
23 B&B
Lowest Price
฿5,376
Highest Price
฿15,027

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.
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 decor. The Cornell Inn, Lenox & The Berkshires: 14.8 mi (23.9 km) from the city centre. Enjoy the free full breakfast and unique decor. 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. The Trail in Adams - Berkshires' Art Hotel: 9 rooms. Located 4.7 mi (7.5 km) from the core of Cheshire. Enjoy the unique decor and patio area.
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 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) 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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