A lake surrounded by autumn-colored trees and hills.

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Check prices for these dates

Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13
In one month
Sep 25 - Sep 27
In two months
Oct 23 - Oct 25

Our top choices for Cheshire bed & breakfast

A large, two-story building with a symmetrical facade, multiple windows, and a central entrance with a covered porch.

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 ￥36,728
￥38,821 total
includes taxes & fees
Aug 27 - Aug 28
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
9.0 out of 10, Wonderful, (154 reviews)
"Great central location for travelers there to see the sights."
United States
Jenna
The price is ￥31,818
￥35,540 total
includes taxes & fees
Sep 16 - Sep 17
The Trail in Adams - Berkshires’ Art Hotel
A red building with a sign reading "Shaker Mill Inn."

3. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (470 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is ￥26,181
￥28,722 total
includes taxes & fees
Aug 31 - Sep 1
Shaker Mill Inn
A snow-covered outdoor area with a patio, seating, and a covered dining area.

4. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,007 reviews)
"The entire staff was amazing and the inn was beautiful, we will definitely be back"
United States
Edward
The price is ￥31,438
￥36,059 total
includes taxes & fees
Aug 26 - Aug 27
The Cornell Inn, Lenox & The Berkshires
An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

5. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (114 reviews)
"Very nice hotel."
United States
Erdem
The price is ￥20,523
￥22,986 total
includes taxes & fees
Aug 26 - Aug 27
Inn at Silver Maple Farm
A garden with a white gazebo, a brick pathway, and various plants and flowers.

6. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very Good, (516 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
The price is ￥25,343
￥28,308 total
includes taxes & fees
Sep 13 - Sep 14
Whistler's Inn Bed & Breakfast
A two-story building with a sign reading "Chambéry Inn".

7. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (386 reviews)
"The room was clean and very quiet. Breakfast was delivered to our room as requested."
United States
Richard
The price is ￥42,952
￥47,978 total
includes taxes & fees
Aug 26 - Aug 27
Chambery Inn
A large, two-story house with a well-maintained lawn and a fence.

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 ￥61,832
￥69,066 total
includes taxes & fees
Sep 3 - Sep 4
Devonfield Inn B&B
A neatly made bed with a headboard, a bedside lamp, a framed painting, and a small bedside table with a tissue box.

9. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is ￥49,541
￥64,820 total
includes taxes & fees
Aug 26 - Aug 27
Experience Timeless Elegance in The Edith Wharton Room!

10. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (103 reviews)
"Our room was very clean and comfortable - exactly what we needed to rest well. Breakfast was excellent and we felt well taken care of. We are grateful for the friendly and welcoming hosts and their staff who listened to every need and graciously provided for us. We’ll definitely return for another stay when we’re in the area."
United Kingdom
Michele
The price is ￥59,974
￥70,341 total
includes taxes & fees
Sep 13 - Sep 14
The Inn at Stockbridge
A modern bathroom with a glass shower, white marble walls, and a large window.

11. 33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (76 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
33 Main
A two-story house with a brick entrance and a white facade.

12. 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, (116 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is ￥57,466
￥69,517 total
includes taxes & fees
Sep 11 - Sep 12
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A room with a dark green sofa, a small table with a vase of flowers, a desk with a lamp, and a window with curtains.

13. Elegant Carriage House room with a queen bed and private patio.

Elegant Carriage House room with a queen bed and private patio.
Lenox
The price is ￥53,359
￥69,733 total
includes taxes & fees
Sep 8 - Sep 9
Elegant Carriage House room with a queen bed and private patio.
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

14. Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (173 reviews)
"Breakfast was not only delicious, the room was sweet and bright and staff very attentive."
United States
Carrie
The price is ￥43,991
￥50,411 total
includes taxes & fees
Aug 30 - Aug 31
Brook Farm Inn
A well-appointed bedroom with a large bed, a bedside table, a chair, and a bathroom visible through an open door.

15. Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
The price is ￥49,541
￥64,820 total
includes taxes & fees
Aug 26 - Aug 27
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
A porch with a white railing, a potted plant, and a view of a garden.

16. Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony
Lenox
The price is ￥54,632
￥71,013 total
includes taxes & fees
Aug 31 - Sep 1
Cozy Carriage House room with a double bed and private balcony
A wooden deck with Adirondack chairs and a small table, leading to a garden area with a swing set.

17. Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is ￥57,177
￥74,289 total
includes taxes & fees
Aug 31 - Sep 1
Historic Susan B. Anthony Room - Cozy & Charming Stay
A bedroom with a bed, a fireplace, a ceiling fan, and a door.

18. Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Lenox
The price is ￥68,631
￥89,203 total
includes taxes & fees
Aug 31 - Sep 1
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
A bedroom with a bed, a television, a fireplace, and a window.

19. "Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
The price is ￥73,722
￥94,074 total
includes taxes & fees
Aug 26 - Aug 27
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
A modern living room with a sloped ceiling, a sofa, a coffee table, and a unique chandelier.

20. Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn

Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Lenox
The price is ￥82,631
￥107,928 total
includes taxes & fees
Sep 3 - Sep 4
Experience Luxury in The Lady Cicely Grand Suite at The Cornell 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

10/10 Excellent
"Very quiet despite being larger area than we thought. Staff at check-in helpful as our card had been corrupted .. manually entered info and we were all set! Enjoyed our balcony very much. lot of fun in the pool !"
Curt 3-night trip
Posted 4 hours ago
Vacation Village in the Berkshires

Find out more about Cheshire

Cheshire B&B information

Number of reviews
2,201
Accommodation
46 B&B
Lowest Price
￥22,986
Highest Price
￥107,928

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. Chambery Inn: 9 rooms. 18.1 mi (29.1 km) from the heart of downtown. Enjoy the private yard and deli. 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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