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

1. 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 ฿8,509
฿8,994 total
includes taxes & fees
3 Aug - 4 Aug
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, (152 reviews)
"Incredible staff, free parking and cute rooms!"
Canada
Priscilla
The price is ฿7,596
฿8,484 total
includes taxes & fees
4 Aug - 5 Aug
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, (1,000 reviews)
"The cornel Inn is terrific! Great location near tanglewood, shops snd restaurants. Great breakfast"
United States
Judith
The price is ฿7,369
฿8,478 total
includes taxes & fees
25 Aug - 26 Aug
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, (465 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is ฿8,586
฿9,419 total
includes taxes & fees
3 Aug - 4 Aug
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, (508 reviews)
"Beautiful inn with the most interesting treasures and decorations."
United States
Mary
The price is ฿5,645
฿6,305 total
includes taxes & fees
3 Aug - 4 Aug
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, (112 reviews)
"Very nice hotel."
United States
Erdem
The price is ฿7,345
฿8,227 total
includes taxes & fees
3 Aug - 4 Aug
Inn at Silver Maple Farm
Front of property

7. 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 ฿9,055
฿10,115 total
includes taxes & fees
30 Aug - 31 Aug
Chambery Inn
Front of property

8. 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 ฿13,644
฿16,003 total
includes taxes & fees
13 Aug - 14 Aug
The Inn at Stockbridge
Front of property – evening/night

9. 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 ฿13,718
฿15,323 total
includes taxes & fees
30 Aug - 31 Aug
Devonfield Inn B&B
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, (114 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is ฿11,074
฿13,396 total
includes taxes & fees
16 Aug - 17 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

11. 33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (75 reviews)
"This was our second stay at 33 Main. Wonderfully maintain, homey environment, with friendly, welcoming and helpful staff. Welcoming cookies, and beautiful water bottle. They even remembered that we asked for the beach and gave us excellent recommendation. Convenient parking in the back. My only suggestion for improvement is breakfast - last year it was much better."
United States
Tatyana
The price is ฿25,092
฿28,028 total
includes taxes & fees
16 Aug - 17 Aug
33 Main
Front of property

12. 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 ฿8,164
฿9,388 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

Berkshires Untold

Berkshires Untold

8/10 Good
"We had a nice stay. Room was comfortable and the staff was great."
Julie 2-night trip
Posted 1 hour ago
Berkshires Untold

Find out more about Cheshire

Cheshire B&B information

Number of reviews
1,228
Accommodation
23 B&B
Lowest Price
฿6,305
Highest Price
฿28,028

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. Chambery Inn: 9 rooms. Situated 18.1 mi (29.1 km) from the heart of Cheshire. Enjoy the private garden and snack bar/deli. Inn at Silver Maple Farm: 11 rooms. Located 18.2 mi (29.3 km) from the core of Cheshire. Enjoy the free buffet breakfast and designer toiletries.
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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