Old Chatham B&B: Find the Best Bed and Breakfast from CA $176

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Our top choices for Old 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

East Chatham

Linda

CA $257 total

includes taxes & fees

Dec 2 - Dec 3

A red building with a sign reading "Shaker Mill Inn."

2. Shaker Mill Inn

West Stockbridge

Mahadeva

CA $222 total

includes taxes & fees

Nov 12 - Nov 13

A snow-covered outdoor area with a patio, seating, and a covered dining area.

3. The Cornell Inn, Lenox & The Berkshires

Lenox

judith

CA $272 total

includes taxes & fees

Nov 15 - Nov 16

A garden with a white gazebo, a brick pathway, and various plants and flowers.

4. Whistler's Inn Bed & Breakfast

Lenox

George

CA $197 total

includes taxes & fees

Nov 6 - Nov 7

A garden with a stone wall, various plants, and a small shed.

5. Gardner Farm Inn

Troy

Karon

CA $284 total

includes taxes & fees

Nov 10 - Nov 11

6. The Inn at Stockbridge

Stockbridge

Kimberly

CA $438 total

includes taxes & fees

Nov 15 - Nov 16

A dining area with a round table and four chairs, a radiator, and a window with a view of greenery.

7. Granville House

Housatonic

Cynthia

CA $398 total

includes taxes & fees

Nov 19 - Nov 20

A two-story house with a brick entrance and a white facade.

8. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Stockbridge

Philippe

CA $615 total

includes taxes & fees

Dec 6 - Dec 7

A dining table with a view of trees and parked cars through a window with wooden shutters.

9. The Morgan State House

Albany

Michael

CA $417 total

includes taxes & fees

Nov 10 - Nov 11

A two-story building with a sign reading "Chambéry Inn".

10. Chambery Inn

Lee

Alexandra

CA $273 total

includes taxes & fees

Nov 8 - Nov 9

A large, two-story house with a well-maintained lawn and a fence.

11. Devonfield Inn B&B

Lee

Sebastien

CA $576 total

includes taxes & fees

Nov 13 - Nov 14

A well-appointed bedroom with a large bed, a bedside table, a chair, and a bathroom visible through an open door.

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

Lenox

CA $472 total

includes taxes & fees

Nov 15 - Nov 16

A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

13. Brook Farm Inn

Lenox

Carrie

CA $270 total

includes taxes & fees

Dec 1 - Dec 2

A neatly made bed with a headboard, a bedside lamp, a framed painting, and a small bedside table with a tissue box.

14. Experience Timeless Elegance in The Edith Wharton Room!

Lenox

CA $472 total

includes taxes & fees

Nov 15 - Nov 16

A porch with a white railing, a potted plant, and a view of a garden.

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

Lenox

CA $527 total

includes taxes & fees

Nov 15 - Nov 16

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.

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

Lenox

CA $500 total

includes taxes & fees

Nov 15 - Nov 16

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

Lenox

CA $556 total

includes taxes & fees

Nov 15 - Nov 16

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

Lenox

CA $680 total

includes taxes & fees

Nov 12 - Nov 13

A bedroom with a bed, a television, a fireplace, and a window.

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

Lenox

CA $719 total

includes taxes & fees

Nov 16 - Nov 17

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

Lenox

CA $820 total

includes taxes & fees

Nov 16 - Nov 17

View all properties

Learn more about Old Chatham

Tucked in the Hudson Valley, this historic hamlet offers peaceful countryside walks and the charming Old Chatham Country Store for local provisions. Nearby Shaker Museum preserves artifacts from America's oldest Shaker settlement, while Chatham's Main Street features independent shops and farm-to-table dining.

See all hotels in Old Chatham

A brick building with a green dome and columns, labeled "TRACY MEMORIAL VILLAGE HALL".

Top reviews in Old Chatham

Inn at Silver Maple Farm

East Chatham

10/10 Excellent

Timothy

Devonfield Inn B&B

Lee

10/10 Excellent

We stayed at the Devonfield Inn in mid-October during peak foliage season. The hotel is a wonderful historic home built in 1800 with much of its historic character preserved. Our hosts were so welcoming and made us feel at home. The room was very comfortable and breakfast was fantastic. In the morning, we got a special surprise to see a bear on the patio drinking from the fountain and robbing the bird feeder. Overall we highly recommend the Devonfield. We will definitely go back.

Lise

The Cornell Inn, Lenox & The Berkshires

Lenox

10/10 Excellent

Michael

Gardner Farm Inn

Troy

10/10 Excellent

Katharine

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Stockbridge

10/10 Excellent

Anonymous traveller

Chambery Inn

Lee

10/10 Excellent

Val

The Morgan State House

Albany

10/10 Excellent

Don

Frequently Asked Questions

What is the nightly rate for a B&B in Old Chatham?

Prices for B&Bs in Old Chatham often vary, but you can find a great deal from CA $176 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Old 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 Old Chatham B&B and a hotel?

Every Old 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 Old Chatham B&Bs.

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Find a Bed and Breakfast in Old Chatham from CA $176

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Old Chatham bed & breakfast

1. Inn at Silver Maple Farm

2. Shaker Mill Inn

3. The Cornell Inn, Lenox & The Berkshires

4. Whistler's Inn Bed & Breakfast

5. Gardner Farm Inn

6. The Inn at Stockbridge

7. Granville House

8. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

9. The Morgan State House

10. Chambery Inn

11. Devonfield Inn B&B

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

13. Brook Farm Inn

14. Experience Timeless Elegance in The Edith Wharton Room!

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

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

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

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

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

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

Learn more about Old Chatham

Top reviews in Old Chatham

Inn at Silver Maple Farm

10/10 Excellent

Frequently Asked Questions

What is the nightly rate for a B&B in Old Chatham?

What is the difference between a Old Chatham B&B and a hotel?

Explore a world of travel with Expedia