A lake surrounded by autumn-colored trees and hills.

Find a Bed and Breakfast in Cheshire from CA $144

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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

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 CA $295
CA $312 total
includes taxes & fees
Dec 2 - Dec 3
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 CA $239
CA $267 total
includes taxes & fees
Dec 8 - Dec 9
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 CA $139
CA $146 total
includes taxes & fees
Nov 8 - Nov 9
UU Rowe Camp and Conference Center
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
9.4 out of 10, Exceptional, (1,002 reviews)
"Lovely room, comfortable bed and a nice breakfast."
United Kingdom
judith
The price is CA $238
CA $273 total
includes taxes & fees
Nov 9 - Nov 10
The Cornell Inn, Lenox & The Berkshires
A garden with a white gazebo, a brick pathway, and various plants and flowers.

5. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.2 out of 10, Very good, (522 reviews)
"Delightful experience in a gilded age setting."
United States
George
The price is CA $192
CA $214 total
includes taxes & fees
Nov 8 - Nov 9
Whistler's Inn Bed & Breakfast
A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

6. 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 CA $230
CA $257 total
includes taxes & fees
Dec 6 - Dec 7
Inn at Silver Maple Farm
A red building with a sign reading "Shaker Mill Inn."

7. 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 CA $203
CA $223 total
includes taxes & fees
Nov 9 - Nov 10
Shaker Mill Inn
Room

8. Cozy Farmhouse Retreat - Ram Dass Room

Cozy Farmhouse Retreat - Ram Dass Room
Rowe
The price is CA $126
CA $144 total
includes taxes & fees
Nov 8 - Nov 9
Cozy Farmhouse Retreat - Ram Dass Room
A two-story building with a sign reading "Chambéry Inn".

9. 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 CA $245
CA $274 total
includes taxes & fees
Nov 8 - Nov 9
Chambery Inn
Front of property

10. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.6 out of 10, Exceptional, (108 reviews)
"Wonderful place… clean, cosy room, comfy bed, friendly staff, great breakfast. Delightful location near Norman Rockwell museum."
United States
Kimberly
The price is CA $343
CA $402 total
includes taxes & fees
Nov 15 - Nov 16
The Inn at Stockbridge
Room

11. Cozy Retreat in historic Farmhouse - Tranquility Room

Cozy Retreat in historic Farmhouse - Tranquility Room
Rowe
The price is CA $182
CA $200 total
includes taxes & fees
Nov 8 - Nov 9
Cozy Retreat in historic Farmhouse - Tranquility Room
A neatly made bed with a headboard, a bedside lamp, a framed painting, and a small bedside table with a tissue box.

12. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is CA $380
CA $474 total
includes taxes & fees
Nov 9 - Nov 10
Experience Timeless Elegance in The Edith Wharton Room!
Room

13. Cozy Retreat in Historic Farmhouse, Charming Bunk Bed Room,- Owl Dorm

Cozy Retreat in Historic Farmhouse, Charming Bunk Bed Room,- Owl Dorm
Rowe
10.0 out of 10, Exceptional, (3 reviews)
"Great space."
United States
Andrew S.
The price is CA $182
CA $200 total
includes taxes & fees
Nov 8 - Nov 9
Cozy Retreat in Historic Farmhouse, Charming Bunk Bed Room,- Owl Dorm
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
9.6 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 CA $232
CA $271 total
includes taxes & fees
Dec 1 - Dec 2
Brook Farm Inn
A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

15. 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 CA $517
CA $578 total
includes taxes & fees
Nov 17 - Nov 18
Devonfield Inn B&B
A two-story house with a brick entrance and a white facade.

16. 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, (120 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is CA $535
CA $648 total
includes taxes & fees
Nov 26 - Nov 27
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A well-appointed bedroom with a large bed, a bedside table, a chair, and a bathroom visible through an open door.

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
The price is CA $380
CA $474 total
includes taxes & fees
Nov 9 - Nov 10
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
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.

18. 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 CA $403
CA $501 total
includes taxes & fees
Nov 9 - Nov 10
Elegant Carriage House room with a queen bed and private patio.
A porch with a white railing, a potted plant, and a view of a garden.

19. 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 CA $425
CA $528 total
includes taxes & fees
Nov 17 - Nov 18
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.

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

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is CA $448
CA $557 total
includes taxes & fees
Nov 9 - Nov 10
Historic Susan B. Anthony Room - Cozy & Charming Stay
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 Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"😊"
NATALYA 3-night trip
Posted 5 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Find out more about Cheshire

Cheshire B&B information

Number of reviews
2,886
Accommodation
46 B&B
Lowest Price
CA $144
Highest Price
CA $648

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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