A lake surrounded by autumn-colored trees and hills.

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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Cheshire bed & breakfast

A large, two-story house with a front porch and a well-maintained garden with various flowers and shrubs.

1. Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.8 out of 10, Exceptional, (58 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is P16,167
P17,089 total
includes taxes & fees
Nov 30 - Dec 1
Harbour House Inn
A wooden cabin interior with a dining area featuring two white chairs, a table with a coffee pot and a cup, and a view into the kitchen through an open doorway.

2. The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
9.2 out of 10, Wonderful, (159 reviews)
"Fun decor, friendly staff, great complimentary breakfast, directly on bike path."
United States
Susan
The price is P11,072
P12,368 total
includes taxes & fees
Nov 16 - Nov 17
The Trail in Adams - Berkshires’ Art Hotel
A house with a chimney, surrounded by trees with autumn foliage.

3. UU Rowe Camp and Conference Center

UU Rowe Camp and Conference Center
2.0 star property
Rowe
10.0 out of 10, Exceptional, (1 review)
"Yes"
United States
Stuart
The price is P6,297
P6,656 total
includes taxes & fees
Nov 17 - Nov 18
UU Rowe Camp and Conference Center
A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

4. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (118 reviews)
"Perfect location for hiking, hanging out and Tanglewood Comfortable and charming common space and cozy nicely decorated rooms Generous breakfast and snacks throughout the day We’ll be back"
United States
Linda
The price is P9,814
P10,991 total
includes taxes & fees
Dec 6 - Dec 7
Inn at Silver Maple Farm
A snow-covered outdoor area with a patio, seating, and a covered dining area.

5. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.4 out of 10, Exceptional, (1,001 reviews)
"Lovely room, comfortable bed and a nice breakfast."
United Kingdom
judith
The price is P10,834
P12,427 total
includes taxes & fees
Nov 16 - Nov 17
The Cornell Inn, Lenox & The Berkshires
A red building with a sign reading "Shaker Mill Inn."

6. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (483 reviews)
"Loved the location, fireplace and vibe"
United States
Mahadeva
The price is P9,240
P10,137 total
includes taxes & fees
Nov 16 - Nov 17
Shaker Mill Inn
Front of property

7. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.6 out of 10, Exceptional, (110 reviews)
"Wonderful place… clean, cosy room, comfy bed, friendly staff, great breakfast. Delightful location near Norman Rockwell museum."
United States
Kimberly
The price is P13,916
P16,322 total
includes taxes & fees
Nov 16 - Nov 17
The Inn at Stockbridge
A two-story building with a sign reading "Chambéry Inn".

8. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (390 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 P13,420
P14,990 total
includes taxes & fees
Dec 15 - Dec 16
Chambery Inn
A two-story house with a brick entrance and a white facade.

9. 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
9.4 out of 10, Exceptional, (121 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is P24,338
P29,443 total
includes taxes & fees
Nov 29 - Nov 30
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

10. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (141 reviews)
"Wonderful location and hosts are amazing. Breakfast was great. Clean."
United States
Sebastien
The price is P23,515
P26,266 total
includes taxes & fees
Nov 16 - Nov 17
Devonfield Inn B&B
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

11. Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.6 out of 10, Exceptional, (178 reviews)
"Breakfast was not only delicious, the room was sweet and bright and staff very attentive."
United States
Carrie
The price is P10,554
P12,298 total
includes taxes & fees
Dec 1 - Dec 2
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"Noisy, even with few people. Tried to take a hot bath and never got more than lukewarm water, I had better luck boiling water on the stove dumping it to warm it up."
Kylie 1-night trip
Posted 4 hours ago
Vacation Village in the Berkshires

Find out more about Cheshire

Cheshire B&B information

Number of reviews
1,482
Accommodation
20 B&B
Lowest Price
P6,656
Highest Price
P29,443

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 attractions in town, Mount Greylock State Reservation and Cheshire Reservoir are worth a stop.
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. 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 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 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 like 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) 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.

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