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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 Chatham bed & breakfast

An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

1. 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 $229
CA $257 total
includes taxes & fees
Dec 2 - Dec 3
Inn at Silver Maple Farm
A red building with a sign reading "Shaker Mill Inn."

2. 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 $222 total
includes taxes & fees
Nov 5 - Nov 6
Shaker Mill Inn
A snow-covered outdoor area with a patio, seating, and a covered dining area.

3. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.4 out of 10, Exceptional, (1,000 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 bedroom with a large mural of a waterfall, two bedside lamps, a bed with multiple pillows, and a nightstand with a lamp.

4. Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (127 reviews)
"A great place to stay!"
United States
Thomas
The price is CA $280
CA $313 total
includes taxes & fees
Nov 5 - Nov 6
Changing Times Boutique Country Lodging
A dining table with pastries, a coffee pot, and a vase of sunflowers.

5. Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (110 reviews)
"We loved everything about Granville House, especially the innkeepers! Wonderful atmosphere and excellent food! It was definitely the highlight of our trip to New England."
United States
Cynthia
The price is CA $357
CA $398 total
includes taxes & fees
Nov 22 - Nov 23
Granville House
A two-story house with a brick entrance and a white facade.

6. 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 $534
CA $646 total
includes taxes & fees
Nov 26 - Nov 27
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A garden with a white gazebo, a brick pathway, and various plants and flowers.

7. 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 $141
CA $157 total
includes taxes & fees
Nov 8 - Nov 9
Whistler's Inn Bed & Breakfast
Front of property

8. 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 $374
CA $438 total
includes taxes & fees
Nov 8 - Nov 9
The Inn at Stockbridge
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 $244
CA $273 total
includes taxes & fees
Nov 5 - Nov 6
Chambery Inn
Interior detail

10. Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (72 reviews)
"Clean, cozy, and charming. The breakfast is delicious and all went smoothly."
United States
Liliana
The price is CA $229
CA $256 total
includes taxes & fees
Nov 12 - Nov 13
Wilder House Berkshires
A large, two-story house with a well-maintained lawn and a fence.

11. 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 $516
CA $576 total
includes taxes & fees
Nov 17 - Nov 18
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.

12. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is CA $380
CA $473 total
includes taxes & fees
Nov 8 - Nov 9
Experience Timeless Elegance in The Edith Wharton Room!
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

13. 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 $270 total
includes taxes & fees
Dec 1 - Dec 2
Brook Farm Inn
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.

14. 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 $402
CA $500 total
includes taxes & fees
Nov 5 - Nov 6
Elegant Carriage House room with a queen bed and private patio.
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 CA $380
CA $473 total
includes taxes & fees
Nov 8 - Nov 9
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 CA $424
CA $527 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.

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

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is CA $447
CA $556 total
includes taxes & fees
Nov 5 - Nov 6
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 CA $547
CA $681 total
includes taxes & fees
Nov 8 - Nov 9
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 CA $592
CA $719 total
includes taxes & fees
Nov 8 - Nov 9
"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 CA $659
CA $820 total
includes taxes & fees
Nov 17 - Nov 18
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 Chatham Hotel Reviews

Berkshires Untold

Berkshires Untold

10/10 Excellent
"Very nice place beautiful view"
Brian 1-night trip
Posted 12 hours ago
Berkshires Untold

Find out more about Chatham

Chatham B&B information

Number of reviews
2,004
Accommodation
40 B&B
Lowest Price
CA $157
Highest Price
CA $820

Frequently asked questions

What is the nightly rate for a Bed & Breakfast in Chatham?
Prices for B&Bs in Chatham often vary, but you can find a great deal from CA $157 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Chatham B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
What is the difference between a Chatham B&B and a hotel?
Every Chatham B&B has its own unique feel. 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 home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Chatham B&Bs.

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